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$300

6 BR / 3 BA / Sleeps 11

Beautiful  Colonial in Secluded Berkshires - Housatonic vacation rentals
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$300

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Beautiful Colonial in Secluded Berkshires

Becket house – 14.3 mi away
6 BR / 3 BA / Sleeps 11 | Quick view

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Enjoy the Fall in our New England farmhouse! Cross country ski at Canterbury Farms, only 5 minutes away! Beautifully restored Colonial historical farmhouse (1790) with almost 2 acres of lawn for playing croquet and hanging out in the sun. There is a small pond (unfenced) for frogs and birds. Large screened in …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Central heating
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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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 – 6.4 mi away
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

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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

2 Reviews

$250

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Berkshires Spacious Comfortable Charming Farmhouse

Lee condo – 8.2 mi away
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

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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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$350

4 BR / 2 BA / Sleeps 9

1 Reviews

$350

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Field View Cottage , Convenient to All Berkshire

Great Barrington house – 6.2 mi away
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

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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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$499

4 BR / 4 BA / Sleeps 12

2 Reviews

$499

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Beautiful New Construction Vacation Home

Stockbridge house – 3.0 mi away
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

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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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$250

3 BR / 2 BA / Sleeps 6

1 Reviews

$250

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Renovated Early 1800s Greek Revival Farmhouse

Stockbridge house – 2.6 mi away
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

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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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$250

5 BR / 2 BA / Sleeps 12

13 Reviews

$250

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Berkshire Farmhouse Vacation

West Stockbridge house – 3.5 mi away
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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$135

3 BR / 1 BA / Sleeps 6

4 Reviews

$135

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Lakeview home with swingset & firepit!

Richmond house – 11.2 mi away
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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Reviews

(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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$360

5 BR / 3 BA / Sleeps 11

8 Reviews

$360

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

Lee house – 10.8 mi away
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

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(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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$300

3 BR / 4 BA / Sleeps 6

1 / 16

$300

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Charming Home Nestled in the Berkshires

Becket house – 16.7 mi away
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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$185

1 BR / 1 BA / Sleeps 2

3 Reviews

$185

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The Smith Farm Homestead

Alford B&B – 2.5 mi away
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

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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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$200

3 BR / 2 BA / Sleeps 8

1 Reviews

$200

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Stockbridge Bowl house

Stockbridge house – 5.2 mi away
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

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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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$140

3 BR / 1 BA / Sleeps 7

1 Reviews

$140

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Lakeside 2Bedroom Home in the Beautiful Berkshires

Richmond house – 11.0 mi away
3 BR / 1 BA / Sleeps 7 | Quick view
“ Poor ” 1 Reviews

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Reviews

(1)

The Berkshires, in Western Massachusetts, are known as center of cultural activities, including but not limited to Tanglewood (the summer home of the Boston Symphony Orchestra), Shakespeare Theatre Festival, Jacobs Pillow, Williamstown Theatre Festival, plus numerous recreational opportunities for hiking, swimming, …
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Balcony or terrace
  • Parking
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(1)

Major Let Down

Left on Sep 10, 2014 for a stay in August 2014

I recently rented this vacation rental with a couple friends to go to Tanglewood and Kripalu. While the house has a lot of potential, it has been very poorly maintained. The owners require that you pay a $75 cleaning fee, but the house was clearly not cleaned before we arrived. The owners also mailed the wrong keys, so we were locked out of the house after Tanglewood until about midnight when …

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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 – 5.8 mi away
3 BR / 2 BA / Sleeps 7 | Quick view
“ Excellent ” 4 Reviews

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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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$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 – 4.2 mi away
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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$149

1 BR / 1 BA / Sleeps 2

5 Reviews

$149

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RiverSong Suite In The Berkshires

North Egremont condo – 4.9 mi away
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 8

1 / 10

$250

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Josiah Loomis Homestead

Richmond house – 10.3 mi away
3 BR / 2 BA / Sleeps 8 | Quick view

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In 1832, Josiah Loomis bought a parcel of land "and the structures thereon", along what was then known as "Massachusetts Turnpike No. 10," the toll road between Albany, NY and Hartford, CT. Josiah Loomis, when he owned this property, could never have imagined what it would look like 180 years later. His 3 room …
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

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$275

5 BR / 4 BA / Sleeps 10

2 Reviews

$275

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Shaker Hill

Great Barrington house – 2.0 mi away
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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$150

4 BR / 1 BA / Sleeps 7

19 Reviews

$150

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Gartner House, a charming home in Lenox

Lenox condo – 8.5 mi away
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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$200

2 BR / 1 BA / Sleeps 4

1 / 10

$200

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Berkshire Schoolhouse Cottage

Great Barrington cottage – 5.6 mi away
2 BR / 1 BA / Sleeps 4 | Quick view

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Welcome to our School House Cottage located in the heart of the Berkshires. Set in front of the ledges of Warner Mountain, this historic home was originally a three room schoolhouse. An addition in the 1960's transformed it into a private home which it remained for many years. Now updated, the cottage has become a …
  • Internet Access
  • Housekeeping Optional
  • A/C or climate control
  • Parking
  • Books
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

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$175

2 BR / 2 BA / Sleeps 6

1 / 4

$175

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Berkshires Rental 15 minutes to Tanglewood

South Lee condo – 4.8 mi away
2 BR / 2 BA / Sleeps 6 | Quick view

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Two Bedroom two bathroom condo located on beautiful resort in the Berkshires. Oak and Spruce Resort located 15 minutes to Tanglewood is the summer home in the Berkshires of the Boston Symphony Orchestra. Condominium sleeps 6 with an eat in kitchen and living area. Recreational activities, ample parking located in …
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

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$375

4 BR / 3 BA / Sleeps 8

16 Reviews

$375

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Beautiful Berkshire House w/ Tennis

Sheffield house – 10.2 mi away
4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 16 Reviews

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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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$125

2 BR / 1 BA / Sleeps 6

2 Reviews

$125

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Cozy & Modern Home -mins from Tanglewood & Kripalu

West Stockbridge condo – 5.6 mi away
2 BR / 1 BA / Sleeps 6 | Quick view
“ Excellent ” 2 Reviews

Details

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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$350

5 BR / 3 BA / Sleeps 10

1 / 9

$350

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Berkshire Lakefront House

Great Barrington house – 1.0 mi away
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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$300

3 BR / 2 BA / Sleeps 6

1 / 23

$300

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Sunroom comfort, spread-out room for everyone

Great Barrington house – 4.4 mi away
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

5 BR / 3 BA / Sleeps 12

1 / 5

$250

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Lakefront Chalet On Pristine Lake/Nature Preserve

Granville chalet – 19.1 mi away
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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$225

1 BR / 1 BA / Sleeps 2

1 / 8

$225

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Romantic Berkshire Cottage on Storybook Estate

Tyringham cottage – 7.9 mi away
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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$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 – 6.8 mi away
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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$250

3 BR / 2 BA / Sleeps 8

1 / 19

$250

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Maya's Garden House

Great Barrington house – 4.3 mi away
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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$199

1 BR / 1 BA / Sleeps 3

12 Reviews

$199

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Berkshires: Romantic Cottage with spectacular view

Great Barrington cottage – 3.5 mi away
1 BR / 1 BA / Sleeps 3 | Quick view
“ Excellent ” 12 Reviews

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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

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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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$100

1 BR / 1 BA / Sleeps 5

1 Reviews

$100

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Yankee Suites Extended Stays

Pittsfield condo – 14.5 mi away
1 BR / 1 BA / Sleeps 5 | Quick view
“ Excellent ” 1 Reviews

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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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$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

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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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$139

2 BR / 2 BA / Sleeps 4

9 Reviews

$139

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Serene Lakefront Cottage

Becket house – 15.9 mi away
2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 9 Reviews

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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

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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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$188

4 BR / 2 BA / Sleeps 10

1 / 12

$188

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Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house – 1.1 mi away
4 BR / 2 BA / Sleeps 10 | Quick view

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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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$175

3 BR / 2 BA / Sleeps 7

13 Reviews

$175

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Berkshires House, 40 wooded acres, Lake Frontage

Monterey house – 10.1 mi away
3 BR / 2 BA / Sleeps 7 | Quick view
“ Excellent ” 13 Reviews

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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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$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 – 4.2 mi away
3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 22 Reviews

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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

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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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$175

4 BR / 6 BA / Sleeps 12

1 / 15

$175

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Spacious wooded home

Becket house – 14.9 mi away
4 BR / 6 BA / Sleeps 12 | Quick view

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Large home in wooded area of the Berkshires. Ideal for all the summer events such as visiting Great Barrington, Lenox, Lee, Stockbridge. Many mountain areas for picnics, biking, hiking in the summer and winter events such as skiing and snowboarding. Near Center pond where there are many boating activities and a beach …
  • Central heating
  • Balcony or terrace
  • Parking
  • Grill
  • Linens Provided

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$130

3 BR / 3 BA / Sleeps 8

1 / 10

$130

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Solid Rock Farm

Stockbridge farmhouse / barn – 3.7 mi away
3 BR / 3 BA / Sleeps 8 | Quick view

Details

Our 1762 Farmhouse is lovingly being restored with gardens in the Berkshires. Mission statement: Educating members in life, farming, and creative art skills acknowledging God as our provider. One mile from the Norman Rockwell Museum and 5 miles from Tanglewood. Come join the farm "Agritourism" experience!
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Central heating
  • Parking
  • Pet friendly - ask
  • Suitable for children

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$375

3 BR / 3 BA / Sleeps 6

1 / 8

$375

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Modern and spacious Colonial with amazing views.

Southfield house – 12.9 mi away
3 BR / 3 BA / Sleeps 6 | Quick view

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Peaceful home set on 3-acres with mountain views and a sunny Southern exposure. Kitchen is oversized with an eating area and a breakfast bar. Front porch and patio, master bedroom with ample storage and private bath with soaking tub. Extra rooms for work or play space. Attached two car garage and mudroom. Close to…
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Patio
  • Parking
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$300

5 BR / 3 BA / Sleeps 12

1 / 10

$300

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Comfortable Farmhouse in the Berkshires

West Stockbridge farmhouse / barn – 5.2 mi away
5 BR / 3 BA / Sleeps 12 | Quick view

Details

Rent a comfortable 1840 farmhouse with 26 acres in the Berkshire mountains. Walk to the village of West Stockbridge or a short drive to all the Berkshire attractions. Close to the ski resorts of Butternut, Bousquet, Catamount and Jiminy Peak. The house sleeps 10 to 12 people and is fully equipped. There's a sewing …
  • Mountain Views
  • Wireless Internet
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Suitable for children

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$200

4 BR / 3 BA / Sleeps 10

1 / 27

$200

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Flower Hill Farm Retreat Apartment/ Entire Retreat

Williamsburg house – 19.1 mi away
4 BR / 3 BA / Sleeps 10 | Quick view

Details

Flower Hill Farm Retreat is housed within a 1790 farmhouse and studio situated on an east facing hillside fifteen minutes west of Northampton, Massachusetts. You can rent the entire retreat or separate apartments. See Rates below in this write up. Rambling organic gardens, fields and forest surround the Retreat …
  • Mountain Views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

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$300

4 BR / 2 BA / Sleeps 8

1 / 12

$300

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Colesbrook Manor

Washington house – 16.8 mi away
4 BR / 2 BA / Sleeps 8 | Quick view

Details

Shingle style, timber frame, passive solar, Berkshie "Cottage" Built along side of Coles Brook, the manor is a retreat destination any time of the year. The seclusion and tranquility of the custom built home and site are unique and comforting for family gatherings and weekend getaways.
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

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$172

3 BR / 2 BA / Sleeps 6

1 / 16

$172

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Charming get-a-way in Great Barrington Berkshires

Great Barrington house – 3.8 mi away
3 BR / 2 BA / Sleeps 6 | Quick view

Details

Charming get-a-way in a friendly residential neighborhood in Great Barrington. Our home is sunny and bright, with an eat-in-kitchen, casual living room and dining area with beautiful picture windows, three comfortable bedrooms, and 1.5 bathrooms. Fully furnished with an eclectic mix of modern and older finds from the …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children

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$200

1 BR / 1 BA / Sleeps 4

1 / 11

$200

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

Lee cottage – 4.6 mi away
1 BR / 1 BA / Sleeps 4 | Quick view

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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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$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 – 3.7 mi away
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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$175

1 BR / 1 BA / Sleeps 2

1 / 2

$175

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chestnut lodge Queens Room

Lee B&B – 9.1 mi away
1 BR / 1 BA / Sleeps 2 | Quick view

Details

Sunny, light , bright and wide! the queens room is one of the biggest rooms and has private ensuite bathroom with tub/shower. 2 big closets, large writing desk, comfy conversation area, 2 dressers full sized bed. a section of the room has original ceilings so persons taller than 6'2" would be happier in the writer'…
  • Pet friendly - ask
  • Suitable for the elderly - ask

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$275

4 BR / 3 BA / Sleeps 8

1 Reviews

$275

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Escape to the Berkshires!

Becket house – 15.5 mi away
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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$150

1 BR / 1 BA / Sleeps 2

1 Reviews

$150

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the yellow room at the chestnut lodge

Lee B&B – 9.2 mi away
1 BR / 1 BA / Sleeps 2 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

first floor queensized bed, bath with shower. floors are wood ceiling has exposed beams and is furnished with oak antiques and a big wingbacked chair.built in bookshelf was from a companionway on a wooden sailing vessel owned by a sea captain that owned and ran the lodge back at the turn of the 20th century. the …
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

I have stayed here several times

Left on Jun 17, 2014 for a stay in June 2013

And I hope to stay here again in the future. I feel very comfortable here - good privacy, the house is huge, rustic charm, generally very quiet. The property is massive - and the region is one of the most beautiful in the world.

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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 – 4.9 mi away
4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 3 Reviews

Details

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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$500

3 BR / 3 BA / Sleeps 8

1 Reviews

$500

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Fall/ Winter- Spectacular Setting-Family- Ski Sled Hike Fish Relax

Stockbridge house – 5.1 mi away
3 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

A home for the family: SKIING, SNOWSHOEING, AND SLEDDING. Fall and Winter availability. Behind the house, on the property is a HUGE hill that is great for sledding. 12 mins to Butternut. 25 mins to Jiminy. Across the road is a park that is great fun to hike, snowshoe, CC ski, and explore. A 1/4 mile driveway …
  • Waterfront
  • Ocean or water views
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Pet friendly
  • Suitable for the elderly

Details

Reviews

(1)

A little piece of paradise!

Left on May 18, 2010 for a stay in July 2009

This house had it all... my wife and I loved our time there. During the day we would either sit on the deck and read or go swimming in our own private lake that was very, very clean. It was close to town for us to go shopping and there were lot's of places to take walks and things to see and do. At night we would make a fire outside in the fire pit and we would soak in the hot tub. The house was …

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