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West Stockbridge Rentals

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141 Houses

Cozy Modern Condo for the Berkshires

West Stockbridge condo

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$296

Comfortable Farmhouse in the Berkshires

West Stockbridge farmhouse

5 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 1 hour 34 minutes

Price per night from

$385

Cozy & Modern Home -mins from Tanglewood & Kripalu

West Stockbridge apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$119

To Ski or Not to Ski? Great conditions Great fireplace.Your Choice.

West Stockbridge house

3 bedrooms / 3 bathrooms / sleeps 8

“A memorable weekend getaway includes the most perfect house..” 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. We also had access to a private quarry that the owners have rights to- bonus! I am quite disappointed that our summer dates are already booked.. but have already started to plan for this Fall.

Responds fast! avg. 2 hours 17 minutes

Price per night from

$415

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

$305

Beautifully Renovated Berkshires Farmhouse

West Stockbridge b&b

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$249

Great rentals within 20 miles that match your search

LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

Lenox house

5 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$534

Luxury Fox Hollow Laurel Lake Ranch

Lenox house

4 bedrooms / 5 bathrooms / sleeps 11

Price per night from

$593

Horse Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$177

Price per night from

$702

Charming Farmhouse on Magical 4 Acre Estate

Tyringham villa

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 1 minutes

Price per night from

$466

Wyndham Bentley Brook Resort

Hancock condo

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 42 minutes

Price per night from

$153

Berkshire Blueberry Lodge LLC - Near Jiminy Peak

Stephentown lodge

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$444

The perfect Southern Berkshire winter vacation esc

Sheffield house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$592

Berkshires Spacious Comfortable Charming Farmhouse

Lee apartment

3 bedrooms / 2 bathrooms / sleeps 8

“lovely stay” 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.

Price per night from

$355

Berkshire Country Estate - Rose Suite

Old Chatham villa

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$201

Big Beautiful 7 bedroom 3 bath hot tub pool table

Pittsfield house

7 bedrooms / 3 bathrooms / sleeps 18

Price per night from

$355

Picturesque 19th century home on 3 private acres

New Marlborough house

4 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$178

Country Retreat w/ Pool Near Hip Hudson, NY

Hudson house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$473

Golden Triangle in the Berkshires

Hancock house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$2,956

Berkshires on the Pond

Becket house

2 bedrooms / 2 bathrooms / sleeps 2

Price per night from

$148

BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES

Otis house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$710

Garfield House

Lee apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$207

7 night Christmas week Wyndham Bentley Brook 2 bdr condo Slopeside

Hancock condo

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$237

Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 4 minutes

Price per night from

$326

Turning Point - Family Retreat & Group Getaway

Great Barrington house

7 bedrooms / 8 bathrooms / sleeps 15

Price per night from

$948

Thanksgiving week lux condo/4 Berkshires

Williamstown condo

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$272

Jiminy Peak Ski Resort-Country Village's Best Unit

Hancock apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$297

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

Hancock house

4 bedrooms / 2 bathrooms / sleeps 9

“Great house Jiminy Peak” We (family of 4) stayed a weekend in January 2010 with friends (family of 5). It is a great house, perfect location and the owner is really great to deal with. Highly recommended for everyone with kids. easy drive to the slopes. well maintained and very clean.

Price per night from

$267

Beautiful Lakefront Berkshire Rental

Monterey house

5 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$506

Cozy and clean in Gt Barrington- available for October

Great Barrington house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$178

Charming Private Guest Suite in Historic Village in the Berkshires

New Marlborough studio

Studio / 1 bathroom / sleeps 2

Price per night from

$113

Gartner House, a charming home in Lenox

Lenox apartment

4 bedrooms / 1 bathroom / sleeps 7

“Great Location In Lenox” My family, friends, & I had a wonderful 2 weeks at Gartner House. It is within easy walking distance of nice shops, terrific restaurants, & a friendly library. Not far are Chesterwood, Tanglewood, Jacob's Pillow, Mass MoCa, Norman Rockwell, & a great, newly renovated Beshire Museum in Pittsfield.

Price per night from

$237

Shaker Hill

Great Barrington house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$445

Cedar Chest

Canaan cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$119

Fabulous Post & Beam Berkshire Rental

Monterey house

/ 2 bathrooms / sleeps 7

Price per night from

$212

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$338

Price per night from

$1,179

Viewing 38 of 141
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
To Ski or Not to Ski? Great conditions Great fireplace.Your Choice.
Incredible vacation stay or seasonal rental

My family rented this home for an entire summer. The house is beautiful and perfectly suited for any sized family. We stayed with two adults and three children (infant-7yrs old), but also had several occasions with overnight guests. Three bedrooms are upstairs, leaving one/two rooms downstairs that functioned as a guest area. It was a perfect scenario with one of the two full bathrooms downstairs, our guests had full privacy. The house is very well kept, comfortable furniture, modern kitchen, and gorgeous views from the 50+ windows! The back yard is huge and our children spent many hours running around and playing freely. We were very pleased with the quietness and safety of the neighborhood. West Stockbridge is a prime and central location for all of the Berkshire's attractions. We have rented seasonal homes in the Berkshires for eleven years and this has been our best experience, by far. The homeowners are extremely welcoming and accommodating, making sure we were comfortable during our stay. We highly recommend this property!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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