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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

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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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$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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$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

Details

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

Charming Home Nestled in the Berkshires - Berkshires vacation rentals
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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$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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Reviews

(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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(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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$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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$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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$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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$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

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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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$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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$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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$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

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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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$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

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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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$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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$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

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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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$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

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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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$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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$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

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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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$250

3 BR / 2 BA / Sleeps 8

1 / 19

$250

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Maya's Garden House

Great Barrington house
3 BR / 2 BA / Sleeps 8 | Quick view

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Surrounded by one of the most beautiful gardens in the Berkshires, Maya's Garden House is an outstanding example of an 18th century barn converted into a modern, comfortable, semi-secluded home. Located less than a mile from Great Barrington, it is close to everything the Berkshires are famous for; Tanglewood, Jacob's…
  • Mountain Views
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly

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$229

2 BR / 2 BA / Sleeps 4

1 Reviews

$229

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Golden Triangle in the Berkshires

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

Details

Reviews

(1)

Cozy ranch home 3 miles away from Jiminy Peak Ski Resort. Near MASS MOCA, Clark Art Institute, Williams College Contemperary Museum of Art, Williamstown Theatre Festival, Tanglewood, shopping, golf courses. Wrap around deck with beautiful mountain views. Family room with full wet bar & flat screen TV to unwind after a…
  • Mountain Views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Spacious, adequate, nice views!

Left on Aug 11, 2013 for a stay in August 2013

Aside from the excessive amount of men's shirts in the closets (closets and drawers had not been emptied so storage space was minimal), the full trash bins and dirty dishes waiting for us on our arrival, we had a very nice stay. Nice mountain view from the deck, mostly clean house, and the three of us and our cat were very comfortable!

Good selection of movies for rainy days, great grill on …

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$150

3 BR / 2 BA / Sleeps 8

1 Reviews

$150

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Berkshire's Getaway ---Peace & Tranquility

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

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Reviews

(1)

House is very private and located on 4 acres of Land. Back yard is peaceful and overlooks ponds. The backyard has a patio/picnic area with gas grill and firepit. One of the ponds has a spurting and lighted fountain that is relaxing ...so have a campfire at night and watch the lighted fountain for a relaxing evening. …
  • Waterfront
  • Mountain Views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(1)

Quaint home on its own lake--don't miss this!

Left on Nov 29, 2014 for a stay in November 2014

The photos speak for themselves. Overall, the home was a great escape from city life, and included its own scenery and lake. My only complaint is that our stay was so short-lived. From our email communication with the owners, they seemed just as charming. We'll be back again.

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$199

1 BR / 1 BA / Sleeps 3

12 Reviews

$199

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Berkshires: Romantic Cottage with spectacular view

Great Barrington cottage
1 BR / 1 BA / Sleeps 3 | Quick view
“ Excellent ” 12 Reviews

Details

Reviews

(12)

Berkshires: Romantic Berkshires Cottage with Stunning Views (Great Barrington) The Berkshires in spring, summer and fall are alive with beauty, and now is the time to plan your restoring getaway in this idyllic studio cottage with its glorious views of the rolling hills and verdant meadows.. Nature lovers, artists…
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Central heating
  • Parking
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly

Details

Reviews

(12)

Peaceful and relaxing weekend

Left on Sep 06, 2011 for a stay in August 2011

My husband and I stayed here while visiting Great Barrington for the weekend. The space is immaculate and very quaintly designed. There is ample space to spread out. Bed is comfortable, full bath is very clean and towels are provided. No stovetop, but a full fridge and kitchen sink. Not much need for a kitchen since downtown is just minutes away and offers plenty of excellent restaurants. The …

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$120

1 BR / 1 BA / Sleeps 4

108 Reviews

$120

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Unique People & Pet-Welcoming Country Haven

Charlemont condo
1 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 108 Reviews

Details

Reviews

(108)

Discover Cavalier Cottage B&B, a pet-friendly home away from your home and an attractive alternative to conventional hotels, motels and B&B's. We warmly welcome visitors who come to this beautiful and diverse area of Western Massachusetts with or without their companion animals. Since opening the cottage in…
  • Mountain Views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(108)

A wonderful place to stay with or without pets.

Left on Mar 15, 2012 for a stay in February 2012

The cottage is clean, full of light and simply decorated. I have stayed in frilly, cutesy, flowery places that felt downright claustrophobic. The full-size kitchen has new appliances and is stocked with everything one could want, from coffee and teas to hot cereal and a variety of fresh fruit. Pat, the proprietor, spoiled me with fresh baked English scones each morning of my stay.
It is …

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$350

5 BR / 3 BA / Sleeps 10

1 / 9

$350

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Berkshire Lakefront House

Great Barrington house
5 BR / 3 BA / Sleeps 10 | Quick view

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Attractive year-round lakefront house in a wooded area on a pristine Round Pond in the Berkshires. Relax and enjoy the view from your deck or dock. Fish from the dock or take the boat out onto the lake. Ideal family retreat in Great Barrington and only a short drive to cultural attractions (Tanglewood, Rockwell Museum…
  • 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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$250

2 BR / 1 BA / Sleeps 5

2 Reviews

$250

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1940's Cabin with fantastic 180o mountain views!!

Great Barrington house
2 BR / 1 BA / Sleeps 5 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Please note that this property is not winterized so it's not available this winter of 2012. I am winterizing this spring & the property will be available on a year around basis stating on 5/15/2013. Please go to (website: hidden) listing #219964 to see my reviews, I am new to flipkey. Located in South Egremont, 3 …
  • Mountain Views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly

Details

Reviews

(2)

What a wonderful cabin! What an amazing location! - The perfect log cabin getaway

Left on May 20, 2013 for a stay in May 2013

This was a perfect weekend for us. I am very picking when choosing a cabin rental because I want it to be "just right--" to fit into all of my ideal visions of the quintessential cozy cabin. Jonathan's Luka Lodge has it-- you feel totally isolated and yet you're only minutes away from delicious restaurants and gourmet shopping. The furnishings and decor are subdued and add to the rustic but …

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$200

2 BR / 2 BA / Sleeps 8

1 / 16

$200

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Wyndham Bentley Brook Jiminy Peak ski in/out

Hancock condo
2 BR / 2 BA / Sleeps 8 | Quick view

Details

Bentley Brook is a ski in/ski out resort located at the base of Jiminy Peak ski resort. On-site Amenities Include: Heated Indoor/Outdoor Pool (year round), 3 hot tubs, 'Get out & Play ' children's program, 3 tennis courts, game room, exercise equipment, sauna, theater with nightly movies.. At Jiminy - Alpine Slide (…
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

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$375

4 BR / 3 BA / Sleeps 8

16 Reviews

$375

Inquire

Beautiful Berkshire House w/ Tennis

Sheffield house
4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 16 Reviews

Details

Reviews

(16)

Enjoy your vacation in a beautiful historic house located in the heart of the Berkshires. Located two and a quarter hours north of New York City, this circa-1770s center chimney colonial will charm and delight your family and guests. 88 acres of land with views of Mt. Washington and Mount Everett promises privacy, …
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(16)

home on the range

Left on Jul 08, 2010 for a stay in May 2003

my wife and i stayed at this lovely home for the entire summer, may through october, and we returned during the new year holiday the following winter. the setting is extremely private and sits on a gorgeous field surrounded on one side by the mountains and the other side of woods and cleared fields with an infinite skyscape, especially interesting on a starry night for heaven seekers.
the home …

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$375

2 BR / 2 BA / Sleeps 6

1 / 5

$375

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July4th Berkshires/James Taylor/2Bed Presidential

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

Details

I have a corner unit first floor 2-bed resort presidential suite in beautiful Berkshires! Just 2 hours drive down the Mass Pike from Boston. It's July 4th week and James Taylor will be playing at Tanglewood. This is one of the most sought after concerts every year and you wouldn't want to miss it! Tanglewood/Lenox is …
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

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$600

2 BR / 2 BA / Sleeps 5

3 Reviews

$600

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July 26 to August 2 Berkshire Oak & Spruce resort

Lee condo
2 BR / 2 BA / Sleeps 5 | Quick view
“ Very Good ” 3 Reviews

Details

Reviews

(3)

Prime week 2br 2ba Berkshire Oak & Spruce resort time share. Full amenities indoor and outdoor pools. Tennis, basketball, mini golf, game room, movie theater on resort. A short drive to tangle wood, lakes etc.
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Housekeeping Optional
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

Peaceful, Quiet, and Scenic

Left on Jun 25, 2014 for a stay in June 2014

I was planning to spend the week traveling around the upper Northeast of the US (Conn, Rhode Island, New Hampsire, Vermont, Maine, and New York.) I chose this resort based on its central location and that it had two bedroom/two bath untis available.

Other than checking in late at night (quite efficient and pleasent by the way), the only other contact I had with resort staff was the minor …

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$185

2 BR / 2 BA / Sleeps 4

9 Reviews

$185

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Serene Lakefront Cottage

Becket house
2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 9 Reviews

Details

Reviews

(9)

Pretty cottage in the woods on a beautiful private lake with a stream running through the property's two acres of land. Newly constructed, spacious and sunny second floor with views of the lake. Hardwood floors throughout the house. Swim, kayak, canoe or fish from the back yard, or just lounge all day watching the …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(9)

Idyllic retreat

Left on Oct 08, 2012 for a stay in October 2012

Quiet rural getaway in a beautiful setting. The backyard ends in the pond shown in the picture, which is surrounded by trees in full fall color. I spent a few hours perched at its edge and lost track of time for the first time in weeks. A complete absence of traffic noise means that the only outside sounds are of running water and rustling leaves, so you can hear yourself breathe. Not much by way…

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$500

4 BR / 3 BA / Sleeps 8

1 / 15

$500

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Charming and Spacious Colonial Farmhouse on 4 Acre Estate

Tyringham villa
4 BR / 3 BA / Sleeps 8 | Quick view

Details

Located on the Santarella Estate, an historic site located in the the Massachussetts' Berkshires. The colonial home is the former residence of sculptor Sir Henry Hudson Kitson. The estate includes the landmark, iconic storybook style 'Gingerbread House,' designed by Kitson to look like an English Country Cottage, the …
  • Mountain Views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

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$300

4 BR / 3 BA / Sleeps 10

1 / 9

$300

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Charming Village- Great House

Housatonic house
4 BR / 3 BA / Sleeps 10 | Quick view

Details

This house is a perfect family retreat in the Berkshires. Nestled in the Village of Housatonic you will be centrally located to all Berkshire attractions. Less that ten minutes from skiing and Tanglewood, as well as the shops and restaurants of Stockbridge, Lenox, and Great Barrington, this is really the ideal …
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Central heating
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

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$188

4 BR / 2 BA / Sleeps 10

1 / 12

$188

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Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house
4 BR / 2 BA / Sleeps 10 | Quick view

Details

Located in a wooded area overlooking a pristine lake, this woodsy style contemporary is a sportsman's paradise. It's a short drive to skiing (Jiminy Peak, Butternut, Catamount) and cultural attractions, (Tanglewood, National Music Center, Aston Magna, etc.) or you can fish, swim, boat, hike, or lounge on the deck and …
  • Waterfront
  • Ocean or water views
  • Mountain Views
  • Internet Access
  • Fireplace
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

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$99

3 BR / 2 BA / Sleeps 6

22 Reviews

$99

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The Cottage B&B near Tanglewood in The Berkshires

Stockbridge B&B
3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 22 Reviews

Details

Reviews

(22)

The Cottage, in picturesque Stockbridge, has the PERFECT location -- minutes from Main Street Lenox, Main Street Stockbridge, The Norman Rockwell Museum, Berkshire Botanical Gardens, Tanglewood Music Festival, The Shrine of the Divine Mercy at the Congregation of Marians, shops, theaters, hiking an biking. Private…
  • Mountain Views
  • Internet Access
  • Housekeeping Optional
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(22)

Location, location, location

Left on Apr 09, 2011 for a stay in August 2006

This place is in one of the absolutely ideal locations in Berkshire Co. You are a 10 minute drive to Tanglewood (and away from all the traffic jams in Lenox and Lee) a walk to Stockbridge center, and Great Barrington is just down Route 7 a few miles. People who want to go to the theatre in Stockbridge or concerts at Tanglewood are nuts not to stay here. If you are not into a breakfast with 5 …

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$150

3 BR / 2 BA / Sleeps 7

13 Reviews

$150

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Berkshires House, 40 wooded acres, Lake Frontage

Monterey house
3 BR / 2 BA / Sleeps 7 | Quick view
“ Excellent ” 13 Reviews

Details

Reviews

(13)

Charming house with the feeling of a cottage, set on a knoll with adjacent cathedral-like pine forest. ** Stone fireplace, woodstove, beautiful kitchen with modern appliances (gas stove, microwave, refrigerator with water/ice dispenser, dishwasher, breadmaker, crockpot, blender, etc.) ** Cathedral-ceiling living area…
  • Waterfront
  • Ocean or water views
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(13)

Awesome Venue!

Left on Jul 17, 2012 for a stay in June 2012

The Hill Cottage is absolutely charming. It is nestled in the forest surrounded by soaring, magnificent pines on a private country road. The atmosphere is very tranquil and peaceful. The cottage is spacious, clean, and well stocked.It is very comfortable and inviting. The cottage is rustic with attractive wide pine floors and knotty pine walls, yet it has very modern amenities including a Jacuzzi…

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$100

4 BR / 3 BA / Sleeps 15

8 Reviews

$100

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Race Mountain House

Sheffield house
4 BR / 3 BA / Sleeps 15 | Quick view
“ Excellent ” 8 Reviews

Details

Reviews

(8)

The Race Mountain House is set high on the slopes of the Taconic Mountains in Southern Berkshire County. Large, east-facing windows look out over a sweeping view of the Housatonic River Valley. In the early hours, the house floods with warm morning light and sunrises are spectacular. The inviting, creative design …
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(8)

Perfect weekend getaway!

Left on Feb 12, 2014 for a stay in December 2013

A truly beautiful house in such a magical place! I spent a lovely weekend here with a group of friends from NYC, and we all had our own space to relax, and enjoyed coming together to cook and unwind in the spacious kitchen and living room (the fire place is awesome!). The perfect spot for a peaceful weekend in the woods, plus it's only a short walk to Race Brook Lodge to enjoy some food and …

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$300

3 BR / 2 BA / Sleeps 5

2 Reviews

$300

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Perfect Getaway for Body, Mind and Soul

Lee cottage
3 BR / 2 BA / Sleeps 5 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

** Rental is only available for 2 week minimum during the summer (July - August) Special Summer Deal -- Rent for the Season (July and August) and get either the last week in June OR the first week in September for half price! This adorable cottage has all the ingredients for the ultimate retreat for body, mind and …
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Washing Machine
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(2)

Great getaway!

Left on Feb 12, 2012 for a stay in August 2011

We had the most amazing time. This adorable home is so close to everything and yet is feels very private and secluded. It provided a perfect balance for relaxation and adventure. One of the best parts for us was the awesome lake. We certainly hope to come back very soon!

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$242

3 BR / 2 BA / Sleeps 6

1 / 15

$242

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Spacious comfortable mid-century modern near town

Lenox house
3 BR / 2 BA / Sleeps 6 | Quick view

Details

In the heart of Lenox, this 2 BR plus study (can be used as a 3BR) house offers the best of both worlds. On nearly 2 park-like acres, the house is a peaceful place for rest and relaxation. But there's much to do nearby. The town center of Lenox is within easy walking distance so you'll be close to restaurants, shops…
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

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$643

6 BR / 6 BA / Sleeps 12

1 / 25

$643

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Berkshire Estate: Exquisitely furnished 7,000sf

Great Barrington villa
6 BR / 6 BA / Sleeps 12 | Quick view

Details

This home is uniquely and magnificently furnished by a retired couple that spent 18 years traveling and living abroad. Even local real estate agents have called the house “special”. It has 7,000 sf of living space (3 floors) with plenty of places to be together or to be alone (as one so chooses). It is on 9 …
  • Mountain Views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$250

3 BR / 2 BA / Sleeps 8

1 / 12

$250

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Charming, secluded 1860's farmhouse

Lenox house
3 BR / 2 BA / Sleeps 8 | Quick view

Details

Charming, spacious and comfortable 1860's farmhouse adjacent to wildlife sanctuary. Cozy country decor with original wide plank floors, lovely views and outdoor dining or lounging on porch or deck. Walking distance to hiking trails in Pleasant Valley Wildlife Preserve or Kennedy Park. Quiet and private, yet …
  • Mountain Views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

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$200

2 BR / 1 BA / Sleeps 5

1 / 19

$200

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Charming Berkshires lakefront house, great views

Cheshire house
2 BR / 1 BA / Sleeps 5 | Quick view

Details

Comfortable house situated on the shore of Hoosac Lake with beautiful, long views stretching across the large lake. It's fully furnished, with cable TV, stereo, and high-speed Internet. There's a big kitchen, with a central island for dining. The expansive living/dining room and attached study, with distinctive wood …
  • Waterfront
  • Ocean or water views
  • Mountain Views
  • Internet Access
  • Washing Machine
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$225

4 BR / 2 BA / Sleeps 10

3 Reviews

$225

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2200sf Country House on 16 Acres-2 Miles to Jiminy

Hancock house
4 BR / 2 BA / Sleeps 10 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

Come and enjoy our beautiful mountain retreat - A home for every season. This charming home away from home is a wonderful place for family, friends and romance. Only 3 minutes from Jiminy Peak! With over 2200 square feet, this new country home has plenty of space for everyone yet a very cozy feel. Each one of the 3…
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(3)

Had a great time!

Left on Oct 07, 2010 for a stay in August 2010

The house was very clean and well supplied. The location is very convenient to fun family activities.


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