
Vacation rentals in West Stockbridge
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Top-rated vacation rentals in West Stockbridge
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Vacation rentals for every style
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Popular amenities for West Stockbridge vacation rentals
Other great vacation rentals in West Stockbridge
Guest favourite

Barn in East Chatham
4.98 out of 5 average rating, 85 reviewsLuxury Barn Retreat — All-Season Escape Awaits!
Guest favourite

Home in Canaan
4.95 out of 5 average rating, 56 reviewsPrivate Retreat: Hot Tub! Movie Room! Pool Table!
Guest favourite

Cottage in Stockbridge
4.94 out of 5 average rating, 34 reviewsQuiet 2 BR cottage in the heart of the Berkshires
Top guest favourite

Home in Canaan
5 out of 5 average rating, 69 reviewsNEW! Berkshires Farmhouse w/ Firepit & Wood Stove
Guest favourite

Home in Richmond
4.95 out of 5 average rating, 20 reviewsSunshine Cottage
Superhost

Home in Great Barrington
4.77 out of 5 average rating, 94 reviewsCozy Berkshire Getaway
Top guest favourite

Loft in Great Barrington
5 out of 5 average rating, 20 reviewsThe Nest 5 min walk to downtown Great Barrington
Guest favourite

Cabin in Austerlitz
4.97 out of 5 average rating, 72 reviewsPinetop Cabin • Near Berkshires + Hudson Valley
Quick stats about vacation rentals in West Stockbridge
Total rentals
70 properties
Nightly prices starting at
$95 CAD before taxes and fees
Total number of reviews
2.2K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Destinations to explore
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- Rentals with a washer and dryer West Stockbridge
- Kid-friendly rentals West Stockbridge
- Family-friendly rentals West Stockbridge
- Rentals with outdoor seating West Stockbridge
- Rentals with a firepit West Stockbridge
- House rentals West Stockbridge
- Rentals with a fireplace West Stockbridge
- Rentals with a patio West Stockbridge
- Pet-friendly rentals West Stockbridge
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- Hunter Mountain
- Six Flags New England
- John Boyd Thacher State Park
- Taconic State Park
- Berkshire East Mountain Resort
- Albany Center Gallery
- Jiminy Peak Mountain Resort
- Zoom Flume
- Bash Bish Falls State Park
- Kent Falls State Park
- Catamount Mountain Ski Resort
- Norman Rockwell Museum
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Windham Mountain
- Beartown State Forest
- Hartford Golf Club
- Mohawk Mountain Ski Area
- Wintonbury Hills Golf Course
- Bright Nights at Forest Park
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Opus 40
- Pineridge Cross Country Ski Area