Stockbridge Rentals

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31 Houses

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One of the Finest Homes and Best location in the Berkshires

Stockbridge house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$801

Expansive Berkshire Property

Stockbridge house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$458

Great rentals within 20 miles that match your search

Lake House

Lee house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 9

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Price per night from

$817

Newly Renovated Lakefront Getaway on Robinson Pond

Copake house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

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$286

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.

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$372

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.

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Price per night from

$486

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.

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$298

Beautifully decorated & immaculate log chalet

Hillsdale log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 14 minutes

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Price per night from

$229

Quiet Comfortable Cabin 5 Min. Walk to Lake

Becket house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“awesome beautiful place” I can't say enough about this. Place, perfect I guess Serene, peaceful,beautiful, quiet. Djuna the owner is Sweet and very efficient and provides every detail. The Whole are is perfect Oct a getaway, things to do places To shop,eat or just cuddle in with a fire. We will Definetly be returning as soon as we can.:)))

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Price per night from

$171

Charming 2+2 Lakeside Cottage on Best Lake in CT

Salisbury cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$206

The Meadow House 4 bdrm 4 bath house

Stephentown house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$721

Spacious Lakeside Berkshire Home

Monterey house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$572

The Barn at Copake Lake

Craryville barn

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 14

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Price per night from

$685

Chalet near 4 ski resorts with hot tub

East Chatham house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,028

CHALET-STYLE STUNNER ON A COUNTRY ROAD

Hillsdale house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$281

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Price per night from

$1,258

Holiday Inn Club Vacations Oak N' Spruce 2br suite Friday check-ins

South Lee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$70

Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$262

Spacious Contemporary With Beautiful Gardens

Housatonic house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$681

Modern Copake Falls Getaway

Copake Falls apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$102

The Stephentown Hotel!

Stephentown b&b

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$109

Holiday Inn Club Vacations Oak N' Spruce 2BR Suite SATURDAY Check-Ins

South Lee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$70

Modern, Private on 40 Acres New Renovation

Ashley Falls house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

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Price per night from

$914

Berkshires: Romantic Cottage with spectacular view

Great Barrington cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

“A Real Gem!!!” This cottage is the perfect place for two people. It is truly as beautiful as the pictures! The pool and grounds are exceptional and the view is breathtaking. The place is extremely well maintained and the owner is very kind and helpful. We had a fabulous weekend here and would gladly return!

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Price per night from

$274

Enjoy horses and the largest recreational lake in Massachusetts

East Otis apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$126

Escape to Avalon Cottage in the Hudson Valley

Craryville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$343

6BR Berkshire Bliss - 38 private acres - close to skiing and town

Lanesborough house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 15

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Price per night from

$794

** Private Berkshire Escape** Monthly Pricing Available

Lee house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$659

Private Berkshire County Retreat

Sheffield house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$686

The Gatehouse on Golden Hill

Lee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$744

Restored 1881 Farm House

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$343

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