Best price vacation rentals in Stockbridge, MA, USA • 150 Listings
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Stockbridge, MA, USA Vacation Rentals | 

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5.0 (45)
Log style home 4 miles to Catamount with fitness room
Up to 7 guests
Airbnb$345
Vrbo$363
Average Nightly Rate
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5.0 (190)
Little gem on Baldwin Hill In South Egremont
Up to 4 guests
Airbnb$224
Vrbo$334
Average Nightly Rate
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5.0 (64)
Newly Remodeled Private Estate! Pool, Tennis Court, 5 Mins to Town & Ski Resorts
Up to 12 guests
Airbnb$738
Vrbo$809
Average Nightly Rate
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5.0 (73)
Twin Maple Farm: Charming Modern Farmhouse
Up to 8 guests
Airbnb$295
Vrbo$295
Average Nightly Rate
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5.0 (123)
Modern And Spacious Berkshires Retreat 5 bdrm 3 bath
Up to 9 guests
Airbnb$446
Vrbo$488
Average Nightly Rate
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5.0 (60)
Historical Downtown 1bedroom
Up to 2 guests
Airbnb$238
Vrbo$238
Average Nightly Rate
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5.0 (34)
Hidden Oasis in the Berkshire Mountains
Up to 10 guests
Airbnb$564
Vrbo$564
Average Nightly Rate

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5.0 (2)
Equipped Villa with Access to Pools, a Hot Tub, 18-Hole Mini Golf, and an Arcade
Up to 8 guests
Airbnb$188
Vrbo$188
Average Nightly Rate
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5.0 (31)
Tranquil Berkshires Retreat
Up to 11 guests
Airbnb$857
Vrbo$936
Average Nightly Rate

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5.0 (27)
One Bedroom Plus Loft, Sleeps 9, Bring The Whole Family!
Up to 9 guests
Airbnb$150
Vrbo$174
Average Nightly Rate
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5.0 (24)
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Up to 8 guests
Airbnb$438
Vrbo$438
Average Nightly Rate
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5.0 (6)
Magic Richmond property with stunning views- 3BR Farmhouse and 2BR Guesthouse.
Up to 12 guests
Airbnb$402
Vrbo$406
Average Nightly Rate
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5.0 (9)
Classic Berkshires cottage in sun-drenched meadow
Up to 8 guests
Airbnb$455
Vrbo$478
Average Nightly Rate
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5.0 (24)
TreeHouse: Berkshires chalet in sun-dappled forest
Up to 6 guests
Airbnb$292
Vrbo$310
Average Nightly Rate
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5.0 (170)
Fantastic cottage in the Berkshire Mountains
Up to 9 guests
Airbnb$354
Vrbo$425
Average Nightly Rate
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5.0 (34)
Beautiful Home in AMAZING Berkshire Location
Up to 10 guests
Airbnb$482
Vrbo$482
Average Nightly Rate
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5.0 (13)
A great escape; secluded but close to all - contemporary home, mountain views
Up to 9 guests
Vrbo$425
Airbnb$495
Average Nightly Rate
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5.0 (35)
NEW! Serene Great Barrington Cottage w/ Fire Pit!
Up to 4 guests
Airbnb$222
Vrbo$224
Average Nightly Rate
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5.0 (18)
Cozy Great Barrington Home ~ 1 Mi to Ski Resort!
Up to 9 guests
Airbnb$328
Vrbo$341
Average Nightly Rate
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5.0 (1)
Warm Welcome Great Barrington, The Berkshires
Up to 10 guests
Airbnb$595
Vrbo$650
Average Nightly Rate
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5.0 (3)
Tentrr Signature Site - Great Barrington Campsite - with Goats and Pool!
Up to 4 guests
Airbnb$169
Vrbo$172
Average Nightly Rate
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5.0 (76)
CABIN FEVER IN STOCKBRIDGE
Up to 6 guests
Airbnb$260
Vrbo$564
Average Nightly Rate
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5.0 (7)
Cozy cottage minutes away from Tanglewood and Stockbridge center
Up to 4 guests
Airbnb$170
Vrbo$170
Average Nightly Rate
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5.0 (2)
Fox Hollow Lakeside Condo, Minutes to Tanglewood
Up to 12 guests
Airbnb$299
Vrbo$299
Average Nightly Rate
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5.0 (25)
Stockbridge Bowl Lake Community
Up to 7 guests
Airbnb$366
Vrbo$385
Average Nightly Rate
  1. United States
  2. Massachusetts
  3. Stockbridge Vacation Rental Price Comparison

Compare Airbnb vs. Booking.com vs. Vrbo prices for vacation rentals in Stockbridge, MA, USA

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