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$300

2 BR / 2 BA / Sleeps 6

9 Reviews

$300

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Wyndham Bentley Brook at Jiminy Peak

Hancock resort
2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 9 Reviews

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Reviews

(9)

On-site Amenities Include: Heated Indoor/Outdoor Pool (year round), Alpine Slide (warmer months), Berkshire Express Chairlift to Summit Lodge during ski season. The Berkshire Express provides scenic rides during warmer months. Bentley Brook is situated Slope Side for SKI/IN - SKI/OUT all winter long. Jiminy Peak …
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(9)

Fall Colors

Left on Oct 04, 2011 for a stay in October 2011

Great location and they really work to keep the place well kept and painted. The beds are very comfortable. Unfortunately the walls are paper thin and the bedrooms butt up against each other. We could hear the conversations of the couple next door without listening-even ear-plugs didn't help. The kitchen has no cabinet to store spices or groceries. Water pressure in showers was very weak. There …

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$250

3 BR / 2 BA / Sleeps 8

2 Reviews

$250

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Berkshires Spacious Comfortable Charming Farmhouse

Lee condo
3 BR / 2 BA / Sleeps 8 | Quick view
“ Very Good ” 2 Reviews

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Reviews

(2)

Experience a little of old New England. Our vacation rental is a charming historic family farmhouse apartment with lots of room and comfort,2100Sq.ft., situated on 22 acres. Built in 1782, our farm was famous for breeding Plymouth Barred Rock chickens. In the 1800's, one of these barred rock roosters won the grand …
  • Mountain Views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(2)

lovely stay

Left on Sep 24, 2010 for a stay in August 2010

The house is comfortable, clean, and convenient to Lenox, Stockbridge, and the rest of the Berkshires. Traffic from the street can be a bit loud at times, but it quiets down at night.

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$265

3 BR / 2 BA / Sleeps 8

3 Reviews

$265

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Rose & Goat Retreat- Mountain Top Lodge

North Adams chalet
3 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 3 Reviews

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Reviews

(3)

Spectacular views are yours from this 2000 square foot Chalet Lodge located on the 50 acre Rose and Goat Retreat on the top of beautiful Florida Mountain in the Berkshires in Western Massachusetts. Enjoy cozy evenings in front of the massive stone fireplace after a day of enjoying all that the the Berkshires has to …
  • Mountain Views
  • Fireplace
  • Outdoor Dining Area
  • Central heating
  • Deck
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - adapted

Details

Reviews

(3)

"Can we stay here for every vacation!"

Left on Feb 01, 2014 for a stay in January 2014

Those are the words of my 15 year old son, who loved every minute at the Rose and Goat Retreat Chalet Lodge!! My husband and I returned to the Rose and Goat after a lovely weekend in October at the Romantic Rose and Goat Retreat, but in the cozy apartment below the Chalet Lodge. This time we were accompanied by 5 teenagers, boys and girls, and they wanted to move right in! We had a beautiful …

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$200

2 BR / 1 BA / Sleeps 4

Retreat in the Woods - Berkshires vacation rentals
1 / 6

$200

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Retreat in the Woods

Savoy house
2 BR / 1 BA / Sleeps 4 | Quick view

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Located in a quiet corner of the northern Berkshires, this lovely two-bedroom home has a combined living room/kitchen with cathedral ceilings and a spacious bathroom complete with a 2-person jacuzzi tub. The house is located about a mile from beautiful Tannery Falls in the Savoy State Forest and other hiking trails …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Porch
  • Parking
  • Suitable for children - over five
  • Suitable for the elderly - ask

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$250

5 BR / 3 BA / Sleeps 12

Beautiful Berkshire post and beam house - Berkshires vacation rentals
1 / 21

$250

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Beautiful Berkshire post and beam house

Monterey house
5 BR / 3 BA / Sleeps 12 | Quick view

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This is a beautiful Berkshire, post and beam private house nestled in the woods just off the Appalachian trail. Set on one of the Berkshires most coveted roads close to fresh water swimming in Lake Garfield, boating, fishing, classical outdoor concerts at Tanglewood & Skiing are all close by. The Space The large…
  • Mountain Views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

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$200

1 BR / 1 BA / Sleeps 4

little blue cottage lots of cute! 1 mile to stockbridge center . pet friendly! - Berkshires vacation rentals
1 / 11

$200

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little blue cottage lots of cute! 1 mile to stockbridge center . pet friendly!

Lee cottage
1 BR / 1 BA / Sleeps 4 | Quick view

Details

cute cozy cottage, screened porch with views, close to everything, sleeps 4 . nice yard with big old trees and soft grass. gas bbq, just one mile to stockbridge center , Berkshire theatre festival. 5 miles to tanglewood, lenox , kripalu. 10 minutes to great barrington. bath has shower. full kitchen with peninsula…
  • Mountain Views
  • Internet Access
  • Fireplace
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

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$250

5 BR / 2 BA / Sleeps 12

13 Reviews

$250

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Berkshire Farmhouse Vacation

West Stockbridge house
5 BR / 2 BA / Sleeps 12 | Quick view
“ Excellent ” 13 Reviews

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Reviews

(13)

Quaint, , 2 story 1850's farmhouse in the Berkshires with original ceiling beams and 16" floor boards in much of the house. Fully furnished with 5 bedrooms, 2 full baths and a gorgeous screened-in porch overlooking 4 acres of gardens, stream and wooded mountains. Country kitchen with dish washer, microwave, toaster …
  • Mountain Views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

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Reviews

(13)

Fantastic place to stay in the Berkshires

Left on Jan 08, 2014 for a stay in December 2013

Elaine was a very gracious host, and the...accommodations were lovely
and in a great location. The historic house has a lot of charm and many
nice updates, especially the clean, updated bathrooms and the huge
screened-in porch. ... We had room to spare, and everyone had a room to
themselves. The kitchen was well stocked, and the living room very cozy...
This would be a great place for skiers. …

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$300

3 BR / 4 BA / Sleeps 6

1 / 16

$300

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Charming Home Nestled in the Berkshires

Becket house
3 BR / 4 BA / Sleeps 6 | Quick view

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Charming 3 bedroom home nestled on 5 acres of secluded woods in the beautiful Berkshire Mountains. Located in the lovely town of Becket on a private road. Completely updated home with a large, open floor plan. Master bedroom with attached private full bathroom on first floor, two additional bedrooms on second …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly

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$135

3 BR / 1 BA / Sleeps 6

4 Reviews

$135

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Lakeview home with swingset & firepit!

Richmond house
3 BR / 1 BA / Sleeps 6 | Quick view
“ Excellent ” 4 Reviews

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Reviews

(4)

Fantastic spot for families and for those looking for a quiet getaway. Come have some summer fun, enjoy the autumn colors or play in the snow. This year round cottage is the perfect spot for those who enjoy outdoor activities. The house is on a private dead end road, has a wonderful lake view and very private …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask

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(4)

Best little hidden treasure

Left on Jul 07, 2010 for a stay in June 2010

We contacted the owners on a referal from a friend and had all our questions answered and more in regards to the propery and its amenities . Upon our arrival we got out of the car and was immediately greeted with a spectacular view of the lake. The house , was immaculate , clean , organized and big enough for me and my family to feel at home. We had a fantastic vacation and I would highly …

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$195

4 BR / 3 BA / Sleeps 7

15 Reviews

$195

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Berkshire Gorge House

New Ashford house
4 BR / 3 BA / Sleeps 7 | Quick view
“ Excellent ” 15 Reviews

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(15)

The Berkshire Gorge House sits beside the Green River above a turbulent set of cascades, on the western slopes of Mt. Greylock. This 5-bedroom house was built in 1910 by New England’s finest craftsmen. It has been recently remodeled and is offered for rent. The house offers a new kitchen with gas range, new washer/…
  • Ocean or water views
  • Mountain Views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

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Reviews

(15)

A peaceful setting minutes away from action and activities

Left on Apr 16, 2012 for a stay in March 2012

A fantastic, rustic house on a wonderful piece of property with easy access to skiing and other activities at Jiminy Peak, historic Williamstown, and the rest of the Berkshires. The house has a ton of character - we especially appreciated its an abundance of rooms and space for us to host friends and family for overnight visits; the new kitchen (including new appliances) was perfect for a ski …

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$300

3 BR / 2 BA / Sleeps 8

7 Reviews

$300

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Berkshire Retreat. Pets Welcome. No Extra Fees.

Hancock house
3 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 7 Reviews

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Reviews

(7)

Secluded mountain home surrounded by 27 acres yet convenient to major attractions including Jiminy Peak, Williamstown, Hancock Shaker Village, Tanglewood, and MassMOCA. Home offers 3 bedrooms and 2 full baths with finished basement recreation room. Updated kitchen with all amenities needed for home cooked meals. …
  • Mountain Views
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Central heating
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(7)

Heaven in Hancock

Left on Sep 18, 2012 for a stay in January 2011

Clean, quiet, and peaceful! This is one of our favorite spots in New England to ski, watch the autumn leaves, and go pumpkin picking. We love to hike on the trails from the back door leading into the woods and past a tranquil stream. The kitchen was recently renovated and we love the open, airy floor plan. Lots of natural light. The deck is huge and a perfect place for barbequing, evening …

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$130

3 BR / 2 BA / Sleeps 7

1 / 8

$130

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New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house
3 BR / 2 BA / Sleeps 7 | Quick view

Details

Located on 19 acres of forest and a creek, mixing modern and traditional with a charming two story wall of windows overlooking a back deck. This comfortable furnished home has two bedrooms with an additional open loft area for a third bedroom, two baths, all hardwood floors, and contains a large kitchen with all new …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Central heating
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

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$149

1 BR / 1 BA / Sleeps 2

5 Reviews

$149

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RiverSong Suite In The Berkshires

North Egremont condo
1 BR / 1 BA / Sleeps 2 | Quick view
“ Excellent ” 5 Reviews

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Reviews

(5)

Located in the Berkshire mountains on more than 5 acres surrounded by 29 acres of conservation land. Featuring beautiful views of meadows, mountains and farm land bordering the crystal clear Green River (great trout fishing).Only 10 minutes from Great Barrington's Main Street stores, resturaunts, theaters, and events…
  • Waterfront
  • Ocean or water views
  • Mountain Views
  • Internet Access
  • Fireplace
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(5)

Enjoyable stay

Left on Aug 23, 2013 for a stay in August 2013

My husband and I stayed 2 nights at Riversong suite - a lower level studio/suite in Barbara and Philip's house. Their property is beautiful overlooking an open field and we enjoyed sitting in the rocking chairs in the gazebo out back. We enjoyed being away from congestion in a peaceful setting. Barbara has thought of everything in terms of furnishing and decorating the space and making sure …

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$250

3 BR / 2 BA / Sleeps 6

1 Reviews

$250

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Renovated Early 1800s Greek Revival Farmhouse

Stockbridge house
3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

Welcome to our family getaway in the Berkshires which we also rent out. Set on 2 acres in the Stockbridge hamlet of Glendale, the house is conveniently located - just a short walk to the Norman Rockwell Museum, Chesterwood House, and Botanical Gardens. The sunny 1st floor features a living room with fireplace open to…
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area

Details

Reviews

(1)

Awesome home and great getaway destination!

Left on Jan 22, 2015 for a stay in October 2014

This home has everything. It also happens to be a wonderfully furnished home. The home owner left little treats for us as we arrived late the first night.

The surrounding towns had great food, fun music, good hiking, solitude and peaceful spots to stop and take in the great views!

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$200

3 BR / 2 BA / Sleeps 8

1 Reviews

$200

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Stockbridge Bowl house

Stockbridge house
3 BR / 2 BA / Sleeps 8 | Quick view
“ Average ” 1 Reviews

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Reviews

(1)

3-bedroom home on lake, near Tanglewood. 2 baths, den, screened porch, large yard.
  • Waterfront
  • Ocean or water views
  • Mountain Views
  • Internet Access
  • Fireplace
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(1)

Great location, tired house

Left on Jul 30, 2014 for a stay in July 2014

Nice house but tired bathrooms and kitchen. One great bedroom, two so so. Hot one nite and needed non existing a/c. Great screened porch with view of water. Canoe was a plus. With a little updating and a good cleaning,it could be fantastic.

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$499

4 BR / 4 BA / Sleeps 12

2 Reviews

$499

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Beautiful New Construction Vacation Home

Stockbridge house
4 BR / 4 BA / Sleeps 12 | Quick view
“ Excellent ” 2 Reviews

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Reviews

(2)

We call this house ‘South Sedgwick’ because of its location on a piece of land formerly used by the Sedgwick family for picnicking–an ideal spot for relaxation with stunning views of Monument Mountain and Ice Glen. The house is newly constructed with ash hardwood floors, custom white pine trim and mahogany …
  • Mountain Views
  • Sauna
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(2)

A true gem. New and beautiful with incredible space and wonderdul amenities, right in the heart of

Left on Jul 18, 2014 for a stay in July 2014

Our family of 5 rented this home over July 4th weekend and we couldn't have been more pleased. The home has just been newly renovated, is very tastefully appointed and looks and feels brand new both inside and out. It also has every amenity we could've hoped for, such as state-of-the-art kitchen appliances, wi-fi, cable TV plus Netflix, dual zone central air, a nice gas grill, multiple outdoor…

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$650

4 BR / 6 BA / Sleeps 12

1 / 22

$650

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Country Elegance in the Berkshires

Great Barrington house
4 BR / 6 BA / Sleeps 12 | Quick view

Details

This immaculate home is the place for relaxing, entertaining and sharing great times with family and friends. The house sets over 4 beautifully wooded acres. We call it the "illision of seclusion," as it is very private and yet is 5 minutes from the town as well as lakes, hiking, movies, theater, shops, …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

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$185

1 BR / 1 BA / Sleeps 2

3 Reviews

$185

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The Smith Farm Homestead

Alford B&B
1 BR / 1 BA / Sleeps 2 | Quick view
“ Excellent ” 3 Reviews

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Reviews

(3)

The Smith Homestead in Alford Massachusetts has been homesteaded and farmed by our family for the past two centuries. Located on one of the nicest settings in the Berkshires, with 30 acres of fields and woods, and the crystal clear Alford Brook running through, we are central to all the cultural events and outdoor …
  • Waterfront
  • Ocean or water views
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Wireless Internet

Details

Reviews

(3)

Beautiful

Left on Apr 09, 2013 for a stay in March 2013

Five stars! Perfect location for a getaway. A quick ride into the beautiful downtown Great Barrington. I have had many good night rests in this room. The hillside view is spectacular. And the best cup of coffee around.

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$360

5 BR / 3 BA / Sleeps 11

8 Reviews

$360

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Bird Watchers Delight! Country Get-Away w/Pond!

Lee house
5 BR / 3 BA / Sleeps 11 | Quick view
“ Very Good ” 8 Reviews

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Reviews

(8)

Beautiful house surrounded by protected woodland and a small beaver pond behind your backyard. All kinds of birds and wildlife. 5 Bedrooms, 2.5 baths, brand new kitchen, open living/dining room, laundry room. Wood stove that can function as a fireplace. 3 heating zones for comfort. All new electric and plumbing in …
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Central heating

Details

Reviews

(8)

Great Girlfriends' Getaway!

Left on Jan 31, 2012 for a stay in January 2012

We decided on fairly short notice to get away with a group of girlfriends to the Berkshires. Robin was so gracious to accommodate us on short notice. We arrived on a frigid day to find a clean and comfortable house, with a fire laid and ready for us. The kitchen had everything we needed for preparing our meals. We especially love the oversized coffee mugs! It's the little things that make a …

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$175

2 BR / 1 BA / Sleeps 4

12 Reviews

$175

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Stone School Cottage

Lanesboro cottage
2 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 12 Reviews

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Reviews

(12)

If you’ve driven by, you’ve wondered about the story of this beautiful stone building. Built in 1832 as a one-room schoolhouse – a function it served until 1950 -- this charming and historic building has been given new life as a vacation getaway. It is perfect for romantic weekends or family adventures. We are …
  • Mountain Views
  • Internet Access
  • Housekeeping Optional
  • Outdoor Dining Area
  • Central heating
  • Suitable for children

Details

Reviews

(12)

Great location, with wonderful scenic spots very close by

Left on Oct 17, 2011 for a stay in October 2011

The best thing about this place was the location. We came here to see the foliage, and we didn't have to go anywhere else driving around looking for it. This is right on the road to Mt Greylock which has so many hiking trails and scenic overlooks.

The Old Stone School cottage is a quaint setup, and the classroom doubles as a bedroom. This is not much of a bedroom, but just a big room with 2 …

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$200

3 BR / 2 BA / Sleeps 6

1 / 13

$200

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Berkshires- 2015 Summer Rental July And August

Hancock condo
3 BR / 2 BA / Sleeps 6 | Quick view

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Luxury condo in hancock, ma ....Three bedrooms, loft, 2 baths, living room, kitchen with dining area, a/c, deck w/grill et al, heated pool, tennis court, mountain view. Near williamstown theater, clark art museum, tanglewood and three local golf courses.
  • Mountain Views
  • Sauna
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Suitable for children
  • Suitable for the elderly

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$189

2 BR / 2 BA / Sleeps 6

1 Reviews

$189

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Berkshires Vacation Rental - Bentley Brook Resort Suite

Hancock condo
2 BR / 2 BA / Sleeps 6 | Quick view
“ Very Good ” 1 Reviews

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Reviews

(1)

A fully furnished and nicely appointed 2br/2ba suite. There's a full kitchen, living room with sofa sleeper, king bed in master bedroom, 2nd bedroom has either a king bed or two queen size beds(varies), washer/dryer, private balcony with mountain or valley views. Everything you need on your vacation. Free parking and…
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(1)

Beautiful area in the fall

Left on Oct 25, 2014 for a stay in October 2014

Lovely place with pool, spa, gym, and movie theater. Units are a bit noisy between floors but otherwise nice and quiet. We had the unfortunate experience of having three small children above us. They enjoyed running and moving furniture. Oh well. Still had a nice stay despite that and a couple of days of rain.

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$122

2 BR / 2 BA / Sleeps 4

1 / 6

$122

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Berkshires on the Pond

Becket house
2 BR / 2 BA / Sleeps 4 | Quick view

Details

Lovely house on pond, Beautiful views of pond from every room, except one. Lounge on the deck with a glass of wine watch the Great Blue Heron has he stalks his fish, see the beavers swim lazily across the pond, flapping their tails to let you know they are there. Every room but one has a water view. Bedroom sleeps …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for the elderly - ask

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$357

5 BR / 5 BA / Sleeps 12

1 / 37

$357

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Elegant 6000+Sf Luxury Estate on 13+ Park

Great Barrington house
5 BR / 5 BA / Sleeps 12 | Quick view

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Bedroom 14, Bathroom 8.75, Sleeps 60 Sitting amongst the apple and lilac trees is our beautifully restored 1790's Captain Jacob Lincoln farmhouse. Enjoy morning coffee on the porch, arrange for a lobster bake on the shore, walk the meandering trails that make their way through 62 private acres of field, forest, and…
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$243

2 BR / 2 BA / Sleeps 4

1 Reviews

$243

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Cozy and clean in Gt Barrington- 1 week in summer!

Great Barrington house
2 BR / 2 BA / Sleeps 4 | Quick view
“ Very Good ” 1 Reviews

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Reviews

(1)

Our home is located in Great Barrington, given the title of the #1 Best Small Town in America by Smithsonian Magazine. There are many great restaurants, shopping, the Mahaiwe theater, a cineplex, golf, natural foods Co-op, a State Forest, yoga studio, and more. There are about twelve (12!) hiking trails in Great …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Porch
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(1)

Easy, comfortable summer getaway!

Left on Feb 02, 2015 for a stay in August 2013

My cousin and I thoroughly enjoyed our stay. The house was cozy and very convenient for our needs. Having a laundry room just off the kitchen was great when we came back from the lake, the bedrooms were airy with cross ventilation and the screened in porch was a great place to linger over coffee in the morning. The location is also wonderful! It is only a 5 minute drive to lake Mansfield, 7or 8 …

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$275

5 BR / 4 BA / Sleeps 10

2 Reviews

$275

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Shaker Hill

Great Barrington house
5 BR / 4 BA / Sleeps 10 | Quick view
“ Very Good ” 2 Reviews

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Reviews

(2)

Shaker Hill is a quirky rambling farmhouse located less than 3 hours from NYC and Boston. Hidden away down a 400’ unpaved driveway on 30 acres of fields and forest in the heart of the Berkshires, Shaker Hill is totally private and surrounded by 30 acres of rolling fields, diverse wetlands, wildlife and forest. It…
  • Mountain Views
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Central heating
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(2)

Big house, private, but a few drawbacks

Left on Sep 11, 2014 for a stay in August 2014

This is a very large house, more than adequate in size for a group of ten people. It has a big yard and a spectacular view of the mountains, especially from an upstairs window. The playroom is a nice touch for those with kids. There are two staircases, which is also nice.

I was under the impression that there were four full bathrooms (which I took to mean with showers). When we arrived, we…

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$200

4 BR / 3 BA / Sleeps 10

1 / 13

$200

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Cosy family house with a swimming pool

Great Barrington condo
4 BR / 3 BA / Sleeps 10 | Quick view

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Sweet cozy house with plenty of room for large groups coming to enjoy the treasures of the Berkshires. Nestled behind Monument Mountain in Great Barrington. 4 bedrooms, 2.5 bathrooms, a spacious kitchen, living room, TV room, game room with pool/Ping-Pong table & two cars garage. Located within a neighborhood friendly…
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask

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$175

2 BR / 1 BA / Sleeps 6

1 / 12

$175

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Berkshire Cottage

Windsor cottage
2 BR / 1 BA / Sleeps 6 | Quick view

Details

Peaceful, mountain hideaway. Rural, yet easily accessible to all major Berkshire County and Pioneer Valley attractions. Recently renovated, this charming 2-bedroom cottage can comfortably accommodate 4-6 people or could be a romantic retreat for two. Full kitchen with all appliances gives you the option of cooking …
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

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$350

4 BR / 2 BA / Sleeps 9

1 Reviews

$350

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Field View Cottage , Convenient to All Berkshire

Great Barrington house
4 BR / 2 BA / Sleeps 9 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

The perfect house for friends and family to share! Bright,uncluttered, and inviting, with privacy and views just minutes to town. There are two fireplaces,a sunken living room, dining room with seating for 10, 4 bedrooms, 2 full bathrooms, and a cozy hang out area in the basement. There is a washer and dryer, …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Best Memorable Thanksgiving Ever

Left on Feb 05, 2015 for a stay in November 2014

This was the first time we had a rental cottage, but it surpassed all of our expectations. The cottage was clean and well arranged. Kitchen was spacious enough for more than a few people cook together. Fireplace was lovely and so fun! The neighborhood was so quiet and calm. It snowed right before Thanksgiving, and the view was priceless! We would like to come back again!

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$145

1 BR / 1 BA / Sleeps 6

1 Reviews

$145

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PanoramicView1000 sq ft Guest Quarters Berkshires

Hancock cottage
1 BR / 1 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Low long term rates. Call $2500/mo for 3 months. Free Electric Vehicle Charging Station! (240V 40A no J1772) Thanksgiving Special - Nov 24 - Dec 1 - $500 Christmas Special - Dec 20 - Dec 27 - $800 Ski Season Dec 1 - Mar 31 $8000 April $50/nt Summer Cultural May 26, 2014 - Seot 2, 2014 $7500 Summer $200/nt Other $150/…
  • Mountain Views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(1)

Clean, Comfortable and Convenient

Left on Oct 16, 2014 for a stay in October 2014

This property is perfect for people with pets.

Serene setting with a gorgeous view. The hosts, Tom and Susan, were gracious and very helpful. Highly recommended if your travels take you to Northwest MA.

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$179

0 BR / 2 BA / Sleeps 7

1 / 11

$179

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Fabulous Post & Beam Berkshire Rental

Monterey house
0 BR / 2 BA / Sleeps 7 | Quick view

Details

You'll love our hand-hewn post & beam beauty on 13 acres in the Berkshire Mountains of Western Mass located near the Monterey/Great Barrington line, close to everything. Great for summer and winter ski season. Rich in both outdoor and cultural attractions, shopping and antiquing. Located adjacent to legendary …
    • Pet friendly - ask
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $225

    3 BR / 2 BA / Sleeps 7

    4 Reviews

    $225

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    Family-friendly Cottage Near Lake, Tanglewood

    Stockbridge cottage
    3 BR / 2 BA / Sleeps 7 | Quick view
    “ Excellent ” 4 Reviews

    Details

    Reviews

    (4)

    Located a short walk to the town beach on the Stockbridge Bowl, and 1.5 miles from Tanglewood's Hawthorn entrance, this casual summer cottage is a great get away for the whole family. The master bedroom is equipped with a queen bed; two twins in the 2nd bedroom, and a full-size bed in the 3rd bedroom. A sofa in the …
    • Internet Access
    • Fireplace
    • Washing Machine
    • Clothes Dryer
    • Deck
    • Suitable for children
    • Suitable for the elderly - ask

    Details

    Reviews

    (4)

    Hidden Gem

    Left on Jul 18, 2013 for a stay in July 2013

    I would like to tell you not to go here. I would like to say stay away, that way it will be availible whenever we want to go back. It is the perfect place to use as a centre to see the area, or sit and do nothing. It was my wife, kids and grand mothers. We did hike, we did spend a day on the beach right by the house, but we also felt at ease to just sit on the screened porch and play cards or …

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    $125

    2 BR / 1 BA / Sleeps 6

    2 Reviews

    $125

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    Cozy & Modern Home -mins from Tanglewood & Kripalu

    West Stockbridge condo
    2 BR / 1 BA / Sleeps 6 | Quick view
    “ Excellent ” 2 Reviews

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    Reviews

    (2)

    Cozy and modern two bedroom and one bath vacation home with lake nearby Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living room, fall foliage and…
    • Internet Access
    • Fireplace
    • Washing Machine
    • Clothes Dryer
    • A/C or climate control
    • Pet friendly - ask
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (2)

    Great home, great location

    Left on Nov 26, 2013 for a stay in November 2013

    Beautiful, modern and cosy home which proved to be a great base for the trip! The fire was an added treat at the end of the day! Location wise the cottage was perfect - close to some wonderful hikes, gorgeous villages and towns and some wonderful food options and restaurants. Already looking forward to the next visit!

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    $275

    4 BR / 3 BA / Sleeps 8

    1 Reviews

    $275

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    Escape to the Berkshires!

    Becket house
    4 BR / 3 BA / Sleeps 8 | Quick view
    “ Excellent ” 1 Reviews

    Details

    Reviews

    (1)

    Come to the Berkshires and stay in one of the most beloved areas of Massachusetts. We are located close to Lenox, Stockbridge, Lee, Great Barrington and more. Our 3400 square foot ranch home is located in the heart of the Berkshires awaiting memorable times with your family and friends. Our local lake is a …
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (1)

    Fabulous Getaway!

    Left on Aug 29, 2014 for a stay in August 2014

    This was our first trip to the Berkshires and we feel fortunate to have found this fabulous home. It suited our needs perfectly as we were traveling with kids and grandparents. The house is set up ideally for this arrangement since there are bedrooms on either side of the house with living room, kitchen, and dining area in the middle. This gives everyone plenty of privacy. We also really …

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    $465

    4 BR / 4 BA / Sleeps 12

    3 Reviews

    $465

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    Gem of the Berkshires, walk to downtown & lake.

    Great Barrington condo
    4 BR / 4 BA / Sleeps 12 | Quick view
    “ Excellent ” 3 Reviews

    Details

    Reviews

    (3)

    This sparkling, newly renovated cottage is for available vacation rental. A stunning sunrise & gorgeous view of the Berkshire Mountains. Conveniently located near many attractions. The house has been renovated by a contemporary designer. It has an open floor plan, making each room flow into another. The main …
    • Mountain Views
    • Wireless Internet
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (3)

    beautiful review and wonderful owners.

    Left on Jul 03, 2012 for a stay in June 2012

    We stayed here for a weekend with friends and couldn't have asked for a better time. The house is located on a hill above Great Barrington and has access to a lake. Ephrat is perhaps the nicest owner I've ever worked with on a vacation rental. She treated us like guests, not renters, and took the time to give us a wonderful tour of the beautiful property. The next morning she even dropped off…

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    $432

    5 BR / 3 BA / Sleeps 14

    1 / 8

    $432

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    Hawk Mountain Lodge at Zoar Outdoor

    Charlemont house
    5 BR / 3 BA / Sleeps 14 | Quick view

    Details

    Hawk Mountain Lodge offers a year-round New England vacation experience! Enjoy comfortable accommodations conveniently located in Charlemont in the northern Berkshires, just 2.5 hours from Boston and 3.5 to 4 hours from New York City. Overlooking the Deerfield River Valley and Berkshire East Ski Resort, our …
    • Ocean or water views
    • Mountain Views
    • Internet Access
    • Housekeeping Optional
    • Central heating
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible

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    $250

    5 BR / 3 BA / Sleeps 12

    1 / 5

    $250

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    Lakefront Chalet On Pristine Lake/Nature Preserve

    Granville chalet
    5 BR / 3 BA / Sleeps 12 | Quick view

    Details

    4 Bedrooms, 3 Baths, 3 Guest Rooms, Open Floor Plan Kitchen, Living, Dining 4 Bedrooms, 3 Baths, 3 Guest Rooms, Open Floor Plan Kitchen, Living, Dining Lakefront, 4 bedrooms, 3 baths, 3 guest rooms, open floor plan with kitchen, living and dining areas, family room, sports room, deck, two balconies and patio. The …
    • Waterfront
    • Ocean or water views
    • Outdoor Dining Area
    • Central heating
    • Deck
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly

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    $300

    3 BR / 2 BA / Sleeps 6

    1 / 23

    $300

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    Sunroom comfort, spread-out room for everyone

    Great Barrington house
    3 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Beautifully furnished, updated 3,000 square foot house. 3 bedrooms, 2 full baths; large sun room with great windows and sky-lights, comfortable seating area for 6 plus cafe table; dining room with table for 6 to 8 people; reading room with a wood-burning stove; living room with a fireplace; private fence-enclosed …
    • Mountain Views
    • Internet Access
    • Fireplace
    • Housekeeping Optional
    • Washing Machine
    • Suitable for children
    • Suitable for the elderly

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    $100

    1 BR / 1 BA / Sleeps 5

    1 Reviews

    $100

    Inquire

    Yankee Suites Extended Stays

    Pittsfield condo
    1 BR / 1 BA / Sleeps 5 | Quick view
    “ Excellent ” 1 Reviews

    Details

    Reviews

    (1)

    A Fully-Furnished Extended Stay property in the Berkshires. Located across the street from the Colonial Theatre and within minutes of most Berkshire County attractions. Each spacious, efficiency (condo-style) single bedroom apartment includes living room, kitchen with full size appliances, bathroom, and deck. Enjoy …
    • Hot Tub/Jacuzzi
    • Internet Access
    • Housekeeping Optional
    • Washing Machine
    • Clothes Dryer
    • Pet friendly
    • Smoking allowed - ask
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (1)

    Excellent Rooms Plus Exceptional Service

    Left on Jul 03, 2013 for a stay in January 2013

    WOW, this place was very nice! What you get is a place with a five minute walk from downtown, well kept buidlings and grounds, excellent floor plans, new furniture, modern kitchen, large closets, a lot of storage space, outside deck, deckbawasher and dryer in the basement, latest technology i.e. cable TV, internet, maid service twice a week.

    Plus a friendly staff on-site seven days a week …

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    $150

    4 BR / 1 BA / Sleeps 7

    19 Reviews

    $150

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    Gartner House, a charming home in Lenox

    Lenox condo
    4 BR / 1 BA / Sleeps 7 | Quick view
    “ Excellent ” 19 Reviews

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    Reviews

    (19)

    Located on a quiet side street in the charming Berkshire town of Lenox, Gartner House is a great place to call home while exploring this scenic, historical, and culturally rich area of Western Massachusetts. Walk to breakfast, lunch or dinner at one of the town's many charming restaurants, explore quirky little shops …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Central heating
    • Pet friendly - ask
    • Suitable for children - ask

    Details

    Reviews

    (19)

    Quaint & Cozy Condo!

    Left on Jan 10, 2012 for a stay in December 2011

    Having stayed at Gartner House a few times, I would recommend it to anyone looking for a comfortable getaway. It is a convenient, short walk to the center of Lenox allowing easy access to all of the wonderful little shops and some great places to eat.
    The condo offers all the comforts of home including full kitchen, land line phone, microwave, washer/dryer and a small side yard. Its spacious …

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    $240

    2 BR / 2 BA / Sleeps 6

    1 / 4

    $240

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    Wyndham Bentley Brook

    Hancock resort
    2 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Ski-In/Ski-Out Plus Year-Round Mountainside Fun. Wyndham Bentley Brook is situated right at the base of Jiminy Peak ski mountain, making this resort an exceptional choice for mountainside play. In winter, ski out your door and onto the lifts. The Two-Bedroom Condos are the ultimate Hancock, Massachusetts vacation …
    • Mountain Views
    • Hot Tub/Jacuzzi
    • Sauna
    • Wireless Internet
    • Washing Machine
    • Suitable for children
    • Suitable for the elderly - elevator access
    • Wheelchair accessible - ask

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    $250

    2 BR / 2 BA / Sleeps 6

    1 / 6

    $250

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    Jiminy Peak Ski Resort-Country Village's Best Unit

    Hancock condo
    2 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Two Bedroom Ski Condo at base of Jiminy Peak. Renovated kitchen, fireplace, deck and a large livingroom with vaulted ceilings. Rent from the owner and save.
    • Fireplace
    • Housekeeping Optional
    • Central heating
    • Linens Provided
    • Towels Provided
    • Suitable for children
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $450

    3 BR / 3 BA / Sleeps 6

    1 / 20

    $450

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    New Pristine Berkshire Vacation Rental with Pool (5 miles Tanglewood)

    Richmond house
    3 BR / 3 BA / Sleeps 6 | Quick view

    Details

    Newly furnished 3 bedroom (with AC) & 2 1/2 bath single family home with stunning deck and in ground pool nestled in the quiet countryside opposite a horse farm. Situated minutes from West Stockbridge convenience stores and restaurants. Property is on 2 quiet tree lined acres with an enclosed idyllic swimming pool …
    • Shared outdoor pool (unheated)
    • Internet Access
    • Fireplace
    • Housekeeping Optional
    • Washing Machine
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly - ask

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    $325

    4 BR / 3 BA / Sleeps 8

    3 Reviews

    $325

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    Historic South Lee Schoolhouse near Stockbridge

    Lee house
    4 BR / 3 BA / Sleeps 8 | Quick view
    “ Excellent ” 3 Reviews

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    Reviews

    (3)

    Enjoy all the Berkshires has to offer in our new (2014) restoration and outstanding renovation of the historic South Lee Schoolhouse. Perched on a hillside just across the road from the Housatonic River and Beartown State Forest in the hamlet of South Lee, just outside of Stockbridge, the 1892 schoolhouse has been …
    • Mountain Views
    • Internet Access
    • Fireplace
    • Washing Machine
    • Clothes Dryer
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly - ask

    Details

    Reviews

    (3)

    spacious, comfortable, and otherwise delightful

    Left on Apr 13, 2015 for a stay in April 2015

    Great place to stay; would be ideal for family groups or others looking for a mix of private spaces and togetherness.

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    $250

    3 BR / 3 BA / Sleeps 7

    5 Reviews

    $250

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    MARCH MADNESS Weekend Special Rate Spring Skiing

    West Stockbridge house
    3 BR / 3 BA / Sleeps 7 | Quick view
    “ Excellent ” 5 Reviews

    Details

    Reviews

    (5)

    Located in West Stockbridge minutes from everything . Nestled in the Berkshire Mountains. Convenient yet Private Visit our web-site at aberkshirehome The Berkshires is a world unto itself. It is scenic beauty married to cultural bounty. It is urban sophistication in an idyllic, rural setting. It is a destination…
    • Mountain Views
    • Internet Access
    • Fireplace
    • Washing Machine
    • Clothes Dryer
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (5)

    A memorable weekend getaway includes the most perfect house..

    Left on Apr 17, 2013 for a stay in July 2012

    My husband and I had the pleasure to rent out this house last summer with another married couple and their son. Although our daughter and their son truly enjoyed Tanglewood and our visits into Town (which are both extremely close), I can't help but think that my favorite part of our vacation was the house we were staying in! The space felt both warm and welcoming and fit our group size perfectly…

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    $250

    3 BR / 2 BA / Sleeps 8

    1 Reviews

    $250

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    N. Adams/Williamstown Exclusive Lakeside Home

    North Adams house
    3 BR / 2 BA / Sleeps 8 | Quick view
    “ Excellent ” 1 Reviews

    Details

    Reviews

    (1)

    Windsor Cottage is a beautiful, newly renovated lakeside retreat located on Windsor Lake in North Adams, MA. where you can enjoy your own private water access from your front lawn. You will feel like you are in the middle of the forest, yet you are in walking distance to the town, Mass MoCA and Massachusetts …
    • Waterfront
    • Ocean or water views
    • Mountain Views
    • Fireplace
    • Outdoor Dining Area
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (1)

    Charming, serene and immaculate cottage on Windsor Lake

    Left on Aug 16, 2014 for a stay in August 2014

    The cottage is well located, seemingly remote, but with nearby access to local attractions and restaurants. I enjoyed sitting on the deck, looking out over the water in the morning - very peaceful. The charming furnishings and immaculately maintained rooms made for a very pleasant stay. I would highly recommend this property.

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    $225

    1 BR / 1 BA / Sleeps 2

    1 / 8

    $225

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    Romantic Berkshire Cottage on Storybook Estate

    Tyringham cottage
    1 BR / 1 BA / Sleeps 2 | Quick view

    Details

    Charming, One Bedroom Cottage, former sculpting studio on the Santarella Estate in Tyringham, MA. Known as the "Silo Studio", there is a bedroom with queen bed upstairs, sitting room, wet bar with Micro/Fridge and bath downstairs. Fall asleep to sounds of babbling brook and views to pond and forest from large screened…
    • Mountain Views
    • Internet Access
    • Housekeeping Optional
    • Outdoor Dining Area
    • Balcony or terrace
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $350

    3 BR / 2 BA / Sleeps 5

    1 / 16

    $350

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    Berkshire Waterfront Home

    Becket house
    3 BR / 2 BA / Sleeps 5 | Quick view

    Details

    Lovey 3 Bedroom house on 200 acres in the Beautiful Berkshires. Drive in, close the gate and enjoy the privacy, sunny lawn leading to a small private lake for swimming, canoeing, fishing. Fully furnished and stocked with everything you need for a stay with family or friends. New bathrooms and kitchen, Pine Cone …
    • Waterfront
    • Ocean or water views
    • Mountain Views
    • Internet Access
    • Fireplace
    • Suitable for children
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $143

    3 BR / 3 BA / Sleeps 6

    1 Reviews

    $143

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    Lake community - Berkshires

    Sandisfield house
    3 BR / 3 BA / Sleeps 6 | Quick view
    “ Excellent ” 1 Reviews

    Details

    Reviews

    (1)

    Home on 2.5 wooded acres in a private lake community, with vacant wooded acres on both sides. Amenities of the community include non-motor boat lake, outdoor heated swimming pool, tennis courts, exercise facility, clubhouse and walking trails. The home is located in the Berkshires, a popular year round destination …
    • Wireless Internet
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Central heating
    • Suitable for children - ask

    Details

    Reviews

    (1)

    Great house in a beautiful lake community

    Left on Feb 01, 2015 for a stay in July 2014

    We stayed at this beautiful house in a lovely lake community. The house is open and bright and very comfortable. We spent most of our time on the large screened back porch, listening to the birds. It's a very short walk to the serene, non-motor boat lake and beach area. When not at the beach or heated community pool, we explored the Berkshires. There were so many things to do....Tanglewood …

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    $100

    2 BR / 1 BA / Sleeps 4

    4 Reviews

    $100

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    The House in Pumpkin Hollow B&B

    Conway house
    2 BR / 1 BA / Sleeps 4 | Quick view
    “ Excellent ” 4 Reviews

    Details

    Reviews

    (4)

    The House in Pumpkin Hollow Bed and Breakfast is nestled in the foothills of the Berkshires in Conway, Masschusetts. It is surrounded by woods. fields, and other historic homes. Ideally situated 6 miles off Route 9, it is close to Northampton, Deerfield, Brattleboro, Amherst and Shelburne Falls. This spacious, 1860 …
    • Mountain Views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • A/C or climate control
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask

    Details

    Reviews

    (4)

    Lovely Stay

    Left on Apr 03, 2014 for a stay in October 2013

    We so enjoyed our stay at The House in Pumpkin Hollow in the sweet town of Conway. We needed a getaway and it was perfect. Diane and her darling dogs greeted us, and she was available for any questions we had. She's a warm and engaging host. The house is stunning with beautiful decor, antiques, large windows and a curving staircase up to our rooms. It was quiet and very private. Nice restaurants …

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