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$357

5 BR / 5 BA / Sleeps 12

Elegant 6000+Sf Luxury Estate on 13+ Park - Berkshires vacation rentals
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$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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$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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$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

Details

Reviews

(8)

Great Girlfriends' Getaway!

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

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

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$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

Beautiful Berkshire post and beam house - Berkshires vacation rentals
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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$195

4 BR / 3 BA / Sleeps 7

15 Reviews

$195

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Berkshire Gorge House

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

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Reviews

(15)

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

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Reviews

(15)

A peaceful setting minutes away from action and activities

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

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

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$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

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$200

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Cosy family house with a swimming pool

4 BR / 3 BA / Sleeps 10 | Quick view

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

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$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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$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

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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

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Reviews

(1)

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

Details

Reviews

(1)

Best Memorable Thanksgiving Ever

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

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

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$465

4 BR / 4 BA / Sleeps 12

3 Reviews

$465

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Gem of the Berkshires, walk to downtown & lake.

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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$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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$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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$432

5 BR / 3 BA / Sleeps 14

1 / 8

$432

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Hawk Mountain Lodge at Zoar Outdoor

5 BR / 3 BA / Sleeps 14 | Quick view

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

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$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

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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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$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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$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

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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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$445

5 BR / 5 BA / Sleeps 16

1 / 17

$445

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House On Main Street

5 BR / 5 BA / Sleeps 16 | Quick view

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Lots of space, great yard, plus you can walk to everything: restaurants, museums, Williams College, theater, night life, etc. This beautifully maintained historic House On Main Street was known as the Victorian Tourist & Antique House in a by-gone era. It was originally constructed in the mid 1700's and was …
  • Wireless Internet
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly - ask
  • Suitable for children
  • Wheelchair accessible - ask

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$300

6 BR / 3 BA / Sleeps 11

1 / 9

$300

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Beautiful Colonial in Secluded Berkshires

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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$375

4 BR / 3 BA / Sleeps 8

16 Reviews

$375

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Beautiful Berkshire House w/ Tennis

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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$300

4 BR / 3 BA / Sleeps 10

1 / 9

$300

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Charming Village- Great 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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$188

4 BR / 2 BA / Sleeps 10

1 / 12

$188

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Lakefront Berkshires Ski/Summer House, Great Views

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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$750

5 BR / 5 BA / Sleeps 12

1 / 7

$750

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Deluxe New Home, 2 Master Suites, Tanglewood Area

5 BR / 5 BA / Sleeps 12 | Quick view

Details

--Brand new 3400 sq ft Lee home in a private lake community, Berkshires --Situated on 4 wooded acres on a quiet country road --Pristine home features two master bedroom suites plus 3 additional bedrooms, 5 bathrooms --Spacious living room with vaulted ceiling & skylights --Fully equipped kitchen, --New 25' Dining …
  • Suitable for children
  • Suitable for the elderly

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$643

6 BR / 6 BA / Sleeps 12

1 / 25

$643

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Berkshire Estate: Exquisitely furnished 7,000sf

6 BR / 6 BA / Sleeps 12 | Quick view

Details

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

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$400

4 BR / 2 BA / Sleeps 10

1 / 18

$400

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LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

4 BR / 2 BA / Sleeps 10 | Quick view

Details

220+ Acres W\ Tennis Cts, Indoor / Outdoor Pool, Canoe, Fishing Boat, Hot Tub. New first time rental of 4 BR, 2BA, Cape Cod style, sleeps 10-12. New fully equipped kitchen w/ center island, indoor and outdoor barbecues, wine cooler, 2 fireplaces, large deck with 8 person hot tub and super seating for beautiful sunsets…
  • Ocean or water views
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

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$100

4 BR / 3 BA / Sleeps 15

8 Reviews

$100

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Race Mountain House

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

Details

Reviews

(8)

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

Details

Reviews

(8)

Perfect weekend getaway!

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

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

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$225

4 BR / 2 BA / Sleeps 10

3 Reviews

$225

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

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

Details

Reviews

(3)

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

Details

Reviews

(3)

Had a great time!

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

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


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