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Houses Great Barrington

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47 houses

Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

4 bedrooms / 2 bathrooms / sleeps 10

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Price per night from

$251

Gem of the Berkshires, walk to downtown & lake.

Great Barrington house

5 bedrooms / 4 bathrooms / sleeps 12

“Wonderful Home!” We had a wonderful weekend! The home and area are lovely - easy walk to town for drinks and dinner - and enjoyed sitting on the many porches, looking out at the view. The home has been upgraded and the kitchen and living areas are beautiful. Thank you!

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$344

Eco-friendly cozy home in Gt. Barrington

Great Barrington house

3 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$171

Impeccable House Minutes from Downtown Great Barrington

Great Barrington house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 3 hours 29 minutes

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Price per night from

$572

Private Home Overlooking Stevens Lake

Great Barrington house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 29 minutes

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Price per night from

$516

NEW! Cozy Great Barrington Home 1 Mi to Ski Resort

Great Barrington house

4 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 1 hour 18 minutes

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Price per night from

$296

Great rentals within 20 miles that match your search

Vacation Home on 10 Acres with Pool and Spa

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$853

Fabulous Post & Beam Berkshire Rental

Monterey house

/ 2 bathrooms / sleeps 7

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$204

Total Privacy! Tanglewood Retreat With Berkshire Views!

Hillsdale house

5 bedrooms / 5 bathrooms / sleeps 14

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Price per night from

$1,137

Evergreen Pines Country Estate Villa

Ancram house

4 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$2,273

Lake House

Lee house

5 bedrooms / 6 bathrooms / sleeps 9

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Price per night from

$812

BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES

Otis house

6 bedrooms / 5 bathrooms / sleeps 14

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Price per night from

$682

Modern Cozy Wooded Retreat

Spencertown house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$152

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 5

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Price per night from

$325

Lake House

Lakeville house

5 bedrooms / 3 bathrooms / sleeps 9

Responds fast! avg. 59 minutes

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Price per night from

$683

My Country Home

Craryville house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 14 minutes

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Price per night from

$171

Chalet near 4 ski resorts with hot tub

East Chatham house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 54 minutes

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Price per night from

$1,024

Deluxe New Home, 2 Master Suites, Tanglewood Area

Lee house

5 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 1 hour 25 minutes

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Price per night from

$855

Spacious Lakeside Berkshire Home

Monterey house

4 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 2 hours 35 minutes

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Price per night from

$512

Private Guest House in Dtwn Lenox, Walk to Dining!

Lenox house

3 bedrooms / 3 bathrooms / sleeps 6

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$216

Hudson Valley Berkshires Cottage

Spencertown house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 55 minutes

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Price per night from

$162

Heart of Lenox

Lenox house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$283

Beautiful Lakefront Berkshire Rental

Monterey house

5 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$624

Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$312

Berkshire Farmhouse Vacation

West Stockbridge house

5 bedrooms / 2 bathrooms / sleeps 15

“Quaint Getaway” We were 2 families with 5 kids staying for the weekend. We had plenty of space to spread out, cook & dine together and lots of bedroom options to meet everyone's needs. The house had a lot of antique charm like exposed beams in the living room and paneled walls in the dining room. We were there on a rainy, cold weekend, so did not have an opportunity to enjoy the grounds or porch, but imagine it would be lovely in the warmer weather. Elaine (and her shop) were on the same grounds and she was available for questions about the area. Overall a very relaxing & convenient experience.

Responds fast! avg. 47 minutes

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Price per night from

$297

LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

Lenox house

5 bedrooms / 3 bathrooms / sleeps 14

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Price per night from

$515

Fox Hollow Laurel Lake Ranch

Lenox house

4 bedrooms / 5 bathrooms / sleeps 11

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Price per night from

$572

Quiet Comfortable Cabin 5 Min. Walk to Lake

Becket house

2 bedrooms / 1 bathroom / sleeps 4

“Great winter getaway spot” My girlfriend and I spent new years at this awesome cabin tucked away in Becket, ma. It was quiet, clean, spacious and just about everything we could have asked for. The property was great, there was lots to do in nearby areas and we had a great time spending nights by the wood stove watching movies on their entertainment setup. I'd definitely recommend it for anyone looking to get out of the city for a few days to just relax and do something different!

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Price per night from

$171

Spacious Contemporary With Beautiful Gardens

Housatonic house

4 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$267

Nature Lover’s Haven: Ski, Golf, Fish, Hike & More

Philmont house

4 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 18 minutes

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Price per night from

$161

Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!

Becket house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 18 minutes

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Price per night from

$385

One of the Finest Homes and Best location in the Berkshires

Stockbridge house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 23 minutes

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Price per night from

$802

Escape to Avalon Cottage in the Hudson Valley

Craryville house

3 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$344

Berkshires Home w/Kayak - Walk to Stockbridge Bowl

Lenox house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 18 minutes

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Price per night from

$219

Cozy Monterey Home w/ Porch: Walk to Lake Garfield

Monterey house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 18 minutes

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Price per night from

$213

Renovated Lakefront House w/ Dock: Pets Welcome!

Monterey house

3 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 18 minutes

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Price per night from

$591

Walk To Tanglewood, Stockbridge Bowl Lake, Wheatleigh

Stockbridge house

3 bedrooms / 5 bathrooms / sleeps 8

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Price per night from

$911

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Lenox house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 18 minutes

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Price per night from

$255

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