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Stockbridge Rentals

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95 Houses

One of the Finest Homes and Best location in the Berkshires

Stockbridge house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 23 minutes

Price per night from

$805

Tranquil 3BR Stockbridge House w/Private Deck

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$339

Vacation Home on 10 Acres with Pool and Spa

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$928

Family-friendly Cottage Near Lake, Tanglewood

Stockbridge cottage

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$328

Horse Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$197

Iris Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$198

"Too Good" AKA 2 Goodrich St.

Stockbridge house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 2 hours 34 minutes

Price per night from

$629

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$323

Great rentals within 20 miles that match your search

BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES

Otis house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$788

Thanksgiving week lux condo/4 Berkshires

Williamstown condo

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$301

Cedar Chest

Canaan cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$132

Fabulous Post & Beam Berkshire Rental

Monterey house

/ 2 bathrooms / sleeps 7

Price per night from

$236

The Meadow House 4 bdrm 4 bath house

Stephentown house

4 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$829

Lake House

Lee house

5 bedrooms / 6 bathrooms / sleeps 9

Price per night from

$939

Modern Cozy Wooded Retreat

Spencertown house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$175

Country estate on 100 acres perfect for families

Chatham house

4 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$1,315

Charming 2+2 Lakeside Cottage on Best Lake in CT

Salisbury cottage

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 50 minutes

Price per night from

$237

Total Privacy! Tanglewood Retreat With Berkshire Views!

Hillsdale house

5 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$1,250

Eco-friendly cozy home in Gt. Barrington

Great Barrington house

3 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$184

Bellavista Country Estate - Rose Suite

Old Chatham villa

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$208

Beautifully Renovated Berkshires Farmhouse

West Stockbridge b&b

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$264

Hudson Valley Berkshires Cottage

Spencertown house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$161

Garfield House

Lee apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$216

7 night Christmas week Wyndham Bentley Brook 2 bdr condo Slopeside

Hancock condo

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$248

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

$612

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

$444

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

$449

Berkshire Blueberry Lodge LLC - Near Jiminy Peak

Stephentown lodge

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$438

Wyndham Bentley Brook Resort

Hancock condo

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$152

Christmas in The Berkshires

Hancock condo

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 39 minutes

Price per night from

$263

Beautiful Lakefront Berkshire Rental

Monterey house

5 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$579

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

$220

Deluxe New Home, 2 Master Suites, Tanglewood Area

Lee house

5 bedrooms / 5 bathrooms / sleeps 12

Price per night from

$858

Spacious Lakeside Berkshire Home

Monterey house

4 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 2 hours 22 minutes

Price per night from

$518

Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$318

Heart of Lenox

Lenox house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 28 minutes

Price per night from

$169

LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

Lenox house

5 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$525

Berkshires: Romantic Cottage with spectacular view

Great Barrington cottage

1 bedroom / 1 bathroom / sleeps 3

“Perhaps the most relaxing vacation I've ever had” The Sigels' cottage was absolutely perfect for us. My husband and I were looking for a nice quiet 4-night stay while our 7-yr-old twins visited with their grandparents. When we arrived everything looked just as in the pictures. The room is sunny, but stays nice and cool too (we were there in august). There is an overhead fan but we didn't even need it. The Sigels made us feel very much at home, but they also seemed to know that we were not looking for a chatty B&B; experience. There are plenty of little touches like a bottle of wine waiting for us, tea, sugar, and some other basics in the kitchenette. A hair dryer, eye shade in the bedside table, etc. But nothing seemed overly fussy-- they are naturally good hosts. The pool was absolutely perfect. Big enough to swim laps, but small enough to be a nice temperature. We spent one whole morning just floating in the pool. The view from the pool is stunning. I am sure there are some amazing hikes around (I had broken my tailbone so hiking will have to wait for next year). Great Barrington is a wonderful town too, so if you're wondering where to stay in the Berkshires, then you would be wise to choose GB. It's not huge, but we never really left town. The walkable part of town has great diners, a cool little coffee shop, a movie theatre, used book store, and great music and food at the Gypsy Joynt (a member of the family that owns it-- Jordan Weller-- put out the best CD I've heard in a long time!) On our last night there the Sigels suggested we go to the Guthrie Center for an open mic where we heard more great music. I can't say enough about the Seigel's cottage. We can't wait to go back next summer.

Price per night from

$268

Viewing 38 of 95
rentals in Stockbridge

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Top Destination reviews

Family-friendly Cottage Near Lake, Tanglewood
Fantastic stay

My friends and I stayed at this cottage couple of weeks and really loved it. It is just a short walk from the Stockbridge Bowl and close to rest of the things Bershires has to offer. The cottage was spacious, plenty on sunlight, very well stocked kitchen that we used extensively, and very useful amenities like nice speaker to which we could connect iPhone.see more

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