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West Stockbridge Rentals

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98 Houses

Cozy Modern Condo for the Berkshires

West Stockbridge condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 35 minutes

Price per night from

$290

Cozy & Modern Home -mins from Tanglewood & Kripalu

West Stockbridge apartment

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 34 minutes

Price per night from

$115

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.

Price per night from

$298

Beautifully Renovated Berkshires Farmhouse

West Stockbridge b&b

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$261

NEW! Cozy Berkshires Cabin - Walk to Beach & Lake!

West Stockbridge cottage

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 14 minutes

Price per night from

$335

Great rentals within 20 miles that match your search

Horse Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$194

Golden Triangle in the Berkshires

Hancock house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$3,240

BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES

Otis house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$778

Thanksgiving week lux condo/4 Berkshires

Williamstown condo

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$298

Cedar Chest

Canaan cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$130

Fabulous Post & Beam Berkshire Rental

Monterey house

/ 2 bathrooms / sleeps 7

Price per night from

$233

The Meadow House 4 bdrm 4 bath house

Stephentown house

4 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$818

Lake House

Lee house

5 bedrooms / 6 bathrooms / sleeps 9

Price per night from

$927

Iris Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$195

Modern Cozy Wooded Retreat

Spencertown house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$173

Country estate on 100 acres perfect for families

Chatham house

4 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$1,299

Stunning New Construction All SeasonLakefront Home

Valatie house

3 bedrooms / 3 bathrooms / sleeps 5

“Fantastic House -- Lake, Poor” Yes, the house is wonderful. Beautiful views abound, it's well stocked with everything you'd want, and extremely clean. A five-star place. That said, the lake's dreadful, in our opinion. It's murky-black. We did go swimming in it, however, but it's so murky you can't see your thighs in the water, much less the bottom. Our twenty-something son wanted to swim across it, and I kept thinking, if he goes under you'd never see him. As it was, he did swim across and we followed in a row boat. We would definitely return were it not for the lake.

Price per night from

$306

Total Privacy! Tanglewood Retreat With Berkshire Views!

Hillsdale house

5 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$1,235

Eco-friendly cozy home in Gt. Barrington

Great Barrington house

3 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$182

Bellavista Country Estate - Rose Suite

Old Chatham villa

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$206

Hudson Valley Berkshires Cottage

Spencertown house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$159

Garfield House

Lee apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$214

7 night Christmas week Wyndham Bentley Brook 2 bdr condo Slopeside

Hancock condo

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$245

Vacation Home on 10 Acres with Pool and Spa

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$916

Chalet near 4 ski resorts with hot tub

East Chatham house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 16 minutes

Price per night from

$605

Lake House w/ Deck & Views, Mins to Jiminy Peak!

Lanesboro cottage

3 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 1 hour 49 minutes

Price per night from

$438

Tanglewood / Berkshires - 2 Bed 2 Bath Apartment

Lee apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 22 minutes

Price per night from

$444

Berkshire Blueberry Lodge LLC - Near Jiminy Peak

Stephentown lodge

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$433

Wyndham Bentley Brook Resort

Hancock condo

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$150

Christmas in The Berkshires

Hancock condo

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 39 minutes

Price per night from

$259

Beautiful Lakefront Berkshire Rental

Monterey house

5 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$572

Outdoor getaway hunting,fishing,skiing..relaxation

Copake house

3 bedrooms / 2 bathrooms / sleeps 9

“Home Away from Home ~ A great place to gather11” Had family coming from New York, Massachusetts and Connecticut to celebrate my birthday ~ hotels, motels are expensive, and they're not home. This house offered a great place to convene ~ outdoor gas grill, eating on the deck, well stocked kitchen and cozy living room. Spacious, comfortable with a lovely master bedroom with private bath. All bedrooms are located somewhat away from the living room which is nice. Walked to the lake with paddles and canoed with my son; got great coffee at the nearby General Store. Michael is wonderful to rent from and very accommodating.

Responds fast! avg. 6 minutes

Price per night from

$217

Deluxe New Home, 2 Master Suites, Tanglewood Area

Lee house

5 bedrooms / 5 bathrooms / sleeps 12

Price per night from

$847

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$319

Brook Hill Farm House

Valatie house

4 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$373

Spacious Lakeside Berkshire Home

Monterey house

4 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 2 hours 22 minutes

Price per night from

$511

Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$314

Heart of Lenox

Lenox house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 28 minutes

Price per night from

$167

Viewing 38 of 98
rentals in West Stockbridge

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Top Destination reviews

Cozy & Modern Home -mins from Tanglewood & Kripalu
Great home, great location

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!see more
Berkshire Farmhouse Vacation
Charming Berkshire Farmhouse

We're a group of five high school friends who get together yearly for a long weekend reunion. Elaine's house was just perfect for us--comfortable, roomy and well equipped not to mention charming! For an older home, it is extremely well maintained. The screened in porch was our favorite place to gather. The location was great with easy access to the many adventures that the area has to offer. Elaine was wonderful to work with and a good host once we arrived. We highly recommend.see more

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