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$72

2 BR / 2 BA / Sleeps 8

2 Reviews

$72

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Wyndham Bentley Brook - 2 Bedroom 2 Bath

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

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Reviews

(2)

The Two-Bedroom Condos are the ultimate Hancock, Massachusetts vacation retreat. Apart from two ultra-spacious private bedrooms and two oversized bathrooms, take advantage of the washer and dryer and fully equipped kitchen for additional travel savings. Create fun filled memories just minutes from Wyndham Bentley …
  • Sauna
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Central heating
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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(2)

Nice place to gather with friends

Left on Aug 19, 2014 for a stay in August 2014

The condo has a full kitchen and living room, making it pleasant to gather with family and/or friends in the evening or on a rainy day.

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$250

3 BR / 2 BA / Sleeps 8

2 Reviews

$250

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Berkshires Spacious Comfortable Charming Farmhouse

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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$135

3 BR / 1 BA / Sleeps 6

4 Reviews

$135

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Lakeview home with swingset & firepit!

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

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Reviews

(4)

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

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(4)

Best little hidden treasure

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

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

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$175

2 BR / 1 BA / Sleeps 4

12 Reviews

$175

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Stone School 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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(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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$250

3 BR / 3 BA / Sleeps 7

5 Reviews

$250

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MARCH MADNESS Weekend Special Rate Spring Skiing

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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$357

5 BR / 5 BA / Sleeps 12

Elegant 6000+Sf Luxury Estate on 13+ Park - Stockbridge vacation rentals
1 / 37

$357

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Elegant 6000+Sf Luxury Estate on 13+ Park

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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$200

4 BR / 3 BA / Sleeps 10

1 / 27

$200

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Flower Hill Farm Retreat Apartment/ Entire Retreat

4 BR / 3 BA / Sleeps 10 | Quick view

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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

4 BR / 2 BA / Sleeps 8 | Quick view

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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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$360

5 BR / 3 BA / Sleeps 11

8 Reviews

$360

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

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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Reviews

(8)

Great Girlfriends' Getaway!

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

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

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$250

5 BR / 2 BA / Sleeps 12

12 Reviews

$250

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Berkshire Farmhouse Vacation

5 BR / 2 BA / Sleeps 12 | Quick view
“ Excellent ” 12 Reviews

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Reviews

(12)

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

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Reviews

(12)

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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$185

1 BR / 1 BA / Sleeps 2

3 Reviews

$185

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The Smith Farm Homestead

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

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!

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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$499

4 BR / 4 BA / Sleeps 12

2 Reviews

$499

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Beautiful New Construction Vacation Home

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

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Reviews

(2)

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

Details

Reviews

(2)

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

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

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

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$250

5 BR / 3 BA / Sleeps 12

1 / 21

$250

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Beautiful Berkshire post and beam house

5 BR / 3 BA / Sleeps 12 | Quick view

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

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$130

3 BR / 2 BA / Sleeps 7

1 / 8

$130

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New Timberframe House Rental in the Berkshire Mountains, Masschusetts

3 BR / 2 BA / Sleeps 7 | Quick view

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

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$250

2 BR / 2 BA / Sleeps 6

1 / 6

$250

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Jiminy Peak Ski Resort-Country Village's Best Unit

2 BR / 2 BA / Sleeps 6 | Quick view

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

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$122

2 BR / 2 BA / Sleeps 4

1 / 6

$122

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Berkshires on the Pond

2 BR / 2 BA / Sleeps 4 | Quick view

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

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$300

2 BR / 2 BA / Sleeps 1

1 Reviews

$300

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Vac Rent Hancock Ma Ski-In Ski Out @ Jiminy Peak

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

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Reviews

(1)

Wyndham Bentley Brook Ski-In Ski Out Wyndham Bentley Brook Resort Ski-In Ski-Out at Jiminy Peak at Wyndham Bentley Brook Resort. Beginners or Experts, we have -programs designed for all levels. After a couple days of skiing, you want to venture out and hit local attractions like, Barrington Stage Company in …
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible - ask

Details

Reviews

(1)

Great, but

Left on Jul 21, 2014 for a stay in July 2014

The condo was great - clean, roomy, stocked with expected items (towels, linens, shampoos, etc.) - my kids felt that it was very hotel-like. Location was perfect for us, although the pool is in a different building (basically need to walk outside and down two sets of steps, not such a big deal.) My one issue is that the price $175 a night was posted, yet I ended up being charged $200 per night …

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$650

4 BR / 6 BA / Sleeps 12

1 / 22

$650

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Country Elegance in the Berkshires

4 BR / 6 BA / Sleeps 12 | Quick view

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

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$200

3 BR / 2 BA / Sleeps 8

1 Reviews

$200

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Stockbridge Bowl 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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$130

1 BR / 1 BA / Sleeps 4

1 / 16

$130

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Cultural Playground 1 bed, walk to Red Lion Inn.

1 BR / 1 BA / Sleeps 4 | Quick view

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One bedroom air conditioned apartment with private entrance in 18th century house in Historic District of Stockbridge. Wonderful views of the river, 18th green of Stockbridge Golf Club and the Berkshire Hills. 5 minutes walk to the famous Red Lion Inn/town center. Self contained and private. You have private bedroom …
  • Waterfront
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Central heating
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

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$179

0 BR / 2 BA / Sleeps 7

1 / 11

$179

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Fabulous Post & Beam Berkshire Rental

0 BR / 2 BA / Sleeps 7 | Quick view

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

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    $350

    5 BR / 4 BA / Sleeps 10

    2 Reviews

    $350

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    Shaker Hill

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

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    Reviews

    (2)

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

    Details

    Reviews

    (2)

    Big house, private, but a few drawbacks

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

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

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

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    $200

    4 BR / 3 BA / Sleeps 10

    1 / 13

    $200

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    Cosy family house with a swimming pool

    4 BR / 3 BA / Sleeps 10 | Quick view

    Details

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

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    $275

    4 BR / 3 BA / Sleeps 8

    1 Reviews

    $275

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    Escape to the Berkshires!

    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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    $300

    3 BR / 2 BA / Sleeps 6

    1 / 23

    $300

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    Sunroom comfort, spread-out room for everyone

    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 Located On Pristine Lake In Natur

    5 BR / 3 BA / Sleeps 12 | Quick view

    Details

    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 house has a unique setting in the heart of a nature preserve and is facing an …
    • 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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    $500

    4 BR / 3 BA / Sleeps 8

    1 / 18

    $500

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    BEAUTIFUL LINDAL CEDAR HOME WITH GREAT LAKE VIEW

    4 BR / 3 BA / Sleeps 8 | Quick view

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    The best place in the world to watch the sunset! Set up high on a hill and nestled amidst the pine trees, this four year old, private and spacious contemporary home overlooks Lake Ashmere (across the road) in Hindsdale. The great room with cathedral ceilings and a wall of windows overlooking the lake, is open to the …
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

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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

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

    Details

    Reviews

    (1)

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

    Details

    Reviews

    (1)

    Best Memorable Thanksgiving Ever

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

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

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    $125

    2 BR / 1 BA / Sleeps 6

    2 Reviews

    $125

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    Cozy & Modern Home -mins from Tanglewood & Kripalu

    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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    $465

    4 BR / 4 BA / Sleeps 12

    3 Reviews

    $465

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    Gem of the Berkshires, walk to downtown & lake.

    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

    2 BR / 1 BA / Sleeps 6

    1 / 12

    $175

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    Berkshire Cottage

    2 BR / 1 BA / Sleeps 6 | Quick view

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

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    $189

    2 BR / 2 BA / Sleeps 6

    1 Reviews

    $189

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    Berkshires Vacation Rental - Bentley Brook Resort Suite

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

    Details

    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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    $350

    5 BR / 3 BA / Sleeps 10

    1 / 9

    $350

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    Berkshire Lakefront 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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    $225

    3 BR / 2 BA / Sleeps 7

    4 Reviews

    $225

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    Family-friendly Cottage Near Lake, Tanglewood

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

    Details

    Reviews

    (4)

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

    Details

    Reviews

    (4)

    Hidden Gem

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

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

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    $157

    2 BR / 2 BA / Sleeps 1

    1 / 9

    $157

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    Rent Hancock Ma.2 Bedroom Vac Village Ski Condo

    2 BR / 2 BA / Sleeps 1 | Quick view

    Details

    This is an amazing 2 Bedroom Condo located in the heart of Berkshires.. On site amenities include, Pool and Game Room. Full Kitchen, 2 Baths and a large Living Room. Western Mass known for its rich culture, which will allow to enjoy close by Jaunts like, Norman Rockwell Museum, Tanglewood etc.. Just one half mile …
    • Mountain Views
    • Hot Tub/Jacuzzi
    • Internet Access
    • A/C or climate control
    • Central heating
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

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    $143

    3 BR / 3 BA / Sleeps 6

    1 Reviews

    $143

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    Lake community - Berkshires

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

    Details

    Reviews

    (1)

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

    Details

    Reviews

    (1)

    Great house in a beautiful lake community

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

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

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    $250

    3 BR / 2 BA / Sleeps 6

    1 Reviews

    $250

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    Renovated Early 1800s Greek Revival Farmhouse

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

    Details

    Reviews

    (1)

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

    Details

    Reviews

    (1)

    Awesome home and great getaway destination!

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

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

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

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    $250

    3 BR / 2 BA / Sleeps 8

    1 / 19

    $250

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    Maya's Garden 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
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Pet friendly
    • Smoking allowed - ask
    • Suitable for children
    • Suitable for the elderly

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    $325

    4 BR / 3 BA / Sleeps 8

    1 / 21

    $325

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    Historic South Lee Schoolhouse near Stockbridge

    4 BR / 3 BA / Sleeps 8 | Quick view

    Details

    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

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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)

    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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    $134

    3 BR / 2 BA / Sleeps 6

    1 / 13

    $134

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    Berkshires- 2015 Summer Rental July And August

    3 BR / 2 BA / Sleeps 6 | Quick view

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

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    $150

    4 BR / 1 BA / Sleeps 7

    19 Reviews

    $150

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    Gartner House, a charming home in Lenox

    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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    $199

    1 BR / 1 BA / Sleeps 3

    12 Reviews

    $199

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    Berkshires: Romantic Cottage with spectacular view

    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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    $500

    4 BR / 3 BA / Sleeps 8

    1 / 15

    $500

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    Charming and Spacious Colonial Farmhouse on 4 Acre Estate

    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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    $250

    2 BR / 1 BA / Sleeps 5

    1 / 14

    $250

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    Lenox Walk to Town / Tanglewood

    2 BR / 1 BA / Sleeps 5 | Quick view

    Details

    This summer cottage built in the 1950's has recently been completely renovated from stem to stern to bring it up to date with the most current design standards. It is a 2-bedroom, 1-bathroom space with a beautiful backyard for grilling. There is also an amazing dining room surrounded by windows and the lush forest …
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly

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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

    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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    $300

    2 BR / 2 BA / Sleeps 6

    8 Reviews

    $300

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    Wyndham Bentley Brook at Jiminy Peak

    2 BR / 2 BA / Sleeps 6 | Quick view
    “ Excellent ” 8 Reviews

    Details

    Reviews

    (8)

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

    Details

    Reviews

    (8)

    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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    $100

    1 BR / 1 BA / Sleeps 5

    1 Reviews

    $100

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    Yankee Suites Extended Stays

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

    Details

    Reviews

    (1)

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

    Details

    Reviews

    (1)

    Excellent Rooms Plus Exceptional Service

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

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

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

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    $500

    3 BR / 2 BA / Sleeps 6

    1 / 11

    $500

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    Vacation Home on 10 Acres with Pool and Spa

    3 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Vacation home centrally located in the Berkshires, 1 mile from Norman Rockwell and 3 miles from Tanglewood, on a quiet country road. Spacious grounds with large 2-level deck overlooking gardens and woods, private in-ground pool with pool house and deck, hot tub. House includes 3 bedrooms, 2 newly renovated baths, …
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly - ask
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