
Holiday rentals in Stockbridge Bowl
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Top-rated holiday rentals in Stockbridge Bowl
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Stockbridge Bowl holiday rentals
Other great holiday rentals in Stockbridge Bowl
Guest favourite

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

Guest house in Stockbridge
4.72 out of 5 average rating, 92 reviewsGuest House in Stockbridge 3 miles to Tanglewood

Cottage in West Stockbridge
4.97 out of 5 average rating, 34 reviewsTanglewood Cottage in the heart of the Berkshires
Guest favourite

Flat in Lee
4.95 out of 5 average rating, 41 reviewsCute, Cozy and Comfortable apartment
Top guest favourite

Cabin in Saugerties
5 out of 5 average rating, 41 reviewsLuxury A-Frame Cabin w/ Hot Tub
Top guest favourite

Home in Great Barrington
4.99 out of 5 average rating, 74 reviewsStunning luxury home with pool
Guest favourite

Cottage in Great Barrington
4.94 out of 5 average rating, 137 reviewsThe Cottage at The Barrington House
Guest favourite

Flat in Lenox
4.89 out of 5 average rating, 64 reviewsThe Penthouse, Downtown Lenox by Evergreen Home
Destinations to explore
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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