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Stockbridge Rentals

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136 Results

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Number of reviews

136 Houses

Restored 1886 Eyebrow Colonial

Stockbridge house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$249

3BD Newly Rennovated Contempoary Near Stockbridge

Stockbridge house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$349

One of the Finest Homes and Best location in the Berkshires

Stockbridge house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$814

Tranquil 3BR Stockbridge House w/Private Deck

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 5 minutes

Price per night from

$266

Vacation Home on 10 Acres with Pool and Spa

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$872

Family-friendly Cottage Near Lake, Tanglewood

Stockbridge cottage

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$327

Cozy Stockbridge Home - Walk To Golf Course!

Stockbridge house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 6 minutes

Price per night from

$249

Horse Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$174

Iris Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$175

"Too Good" With 11 Private Acres. Contact us for Monthly Specials!

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

$332

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

$524

Luxury Fox Hollow Laurel Lake Ranch

Lenox house

4 bedrooms / 5 bathrooms / sleeps 11

Price per night from

$582

Price per night from

$689

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

$458

Wyndham Bentley Brook Resort

Hancock condo

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 42 minutes

Price per night from

$150

Berkshire Blueberry Lodge LLC - Near Jiminy Peak

Stephentown lodge

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$436

The perfect Southern Berkshire winter vacation esc

Sheffield house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$581

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

$348

Berkshire Country Estate - Rose Suite

Old Chatham villa

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$198

Big Beautiful 7 bedroom 3 bath hot tub pool table

Pittsfield house

7 bedrooms / 3 bathrooms / sleeps 18

Price per night from

$348

Picturesque 19th century home on 3 private acres

New Marlborough house

4 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$174

Country Retreat w/ Pool Near Hip Hudson, NY

Hudson house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$465

Berkshires on the Pond

Becket house

2 bedrooms / 2 bathrooms / sleeps 2

Price per night from

$145

Beautifully Renovated Berkshires Farmhouse

West Stockbridge b&b

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$244

Spacious Lakeside Berkshire Home

Monterey house

4 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$523

BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES

Otis house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$697

Garfield House

Lee apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$203

7 night Christmas week Wyndham Bentley Brook 2 bdr condo Slopeside

Hancock condo

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$232

Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 4 minutes

Price per night from

$320

Turning Point - Family Retreat & Group Getaway

Great Barrington house

7 bedrooms / 8 bathrooms / sleeps 15

Price per night from

$930

Thanksgiving week lux condo/4 Berkshires

Williamstown condo

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$267

Jiminy Peak Ski Resort-Country Village's Best Unit

Hancock apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$291

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

$262

Beautiful Lakefront Berkshire Rental

Monterey house

5 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$497

Cozy and clean in Gt Barrington- available for October

Great Barrington house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$175

Charming Private Guest Suite in Historic Village in the Berkshires

New Marlborough studio

Studio / 1 bathroom / sleeps 2

Price per night from

$111

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

$233

Viewing 38 of 136
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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