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Stockbridge Rentals

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66 Houses

Vacation Home on 10 Acres with Pool and Spa

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$856

Horse Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$171

One of the Finest Homes and Best location in the Berkshires

Stockbridge house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$802

Iris Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$171

"Too Good" AKA 2 Goodrich St.

Stockbridge house

4 bedrooms / 4 bathrooms / sleeps 12

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

$325

Walk To Tanglewood, Stockbridge Bowl Lake, Wheatleigh

Stockbridge house

3 bedrooms / 5 bathrooms / sleeps 8

Price per night from

$911

Great rentals within 20 miles that match your search

Garfield House

Lee apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$200

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

$371

Hillhouse Log Cabin

Hillsdale log cabin

3 bedrooms / 2 bathrooms / sleeps 13

“rest,relax,recharge” It's a Beautiful home that has all the modern conveniences. It's quiet, quaint and had just what I needed to get away from it all. I enjoyed morning coffee on the back deck among the trees and afternoon walks in the woods. A perfect place to recharge.

Price per night from

$485

LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

Lenox house

5 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$514

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. 21 minutes

Price per night from

$297

Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$314

Bentley/Wyndham Hancock Mass at Jiminy Peak

Hancock condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$428

Deluxe New Home, 2 Master Suites, Tanglewood Area

Lee house

5 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 1 hour 42 minutes

Price per night from

$856

Eco-friendly cozy home in Gt. Barrington

Great Barrington house

3 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$171

Beautifully decorated & immaculate log chalet

Hillsdale log cabin

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 39 minutes

Price per night from

$228

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!

Price per night from

$170

Charming 2+2 Lakeside Cottage on Best Lake in CT

Salisbury cottage

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$206

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

$228

The Meadow House 4 bdrm 4 bath house

Stephentown house

4 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$719

Fabulous Post & Beam Berkshire Rental

Monterey house

/ 2 bathrooms / sleeps 7

Price per night from

$205

Total Privacy! Tanglewood Retreat With Berkshire Views!

Hillsdale house

5 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$1,141

Lake House

Lee house

5 bedrooms / 6 bathrooms / sleeps 9

Price per night from

$815

Christmas in The Berkshires

Hancock condo

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 28 minutes

Price per night from

$257

Modern Cozy Wooded Retreat

Spencertown house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$152

Thanksgiving week lux condo/4 Berkshires

Williamstown condo

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$262

Fox Hollow Laurel Lake Ranch

Lenox house

4 bedrooms / 5 bathrooms / sleeps 11

Price per night from

$571

Spacious Lakeside Berkshire Home

Monterey house

4 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 1 hour 10 minutes

Price per night from

$571

Heart of Lenox

Lenox house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 17 minutes

Price per night from

$285

The Barn at Copake Lake

Craryville barn

3 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$683

Hudson Valley Berkshires Cottage

Spencertown house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 0 minutes

Price per night from

$163

Chalet near 4 ski resorts with hot tub

East Chatham house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,026

The Heart of Berkshires

Lee house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$400

CHALET-STYLE STUNNER ON A COUNTRY ROAD

Hillsdale house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$280

Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$262

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$217

Tentrr Signature Site - Great Barrington Campsite - With Pool!

Great Barrington tented camp

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$103

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