
Vacation rentals in Cheshire
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Top-rated vacation rentals in Cheshire
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Popular amenities for Cheshire vacation rentals
Other great vacation rentals in Cheshire

Guest suite in Hancock
4.81 out of 5 average rating, 180 reviewsCozy apartment near Jiminy Peak
Guest favorite

Cabin in Windsor
4.91 out of 5 average rating, 11 reviewsStone cabin in the Berkshires
Guest favorite

Cabin in Cambridge
4.97 out of 5 average rating, 33 reviewsPond View Cabin. Off-Grid, Rustic & Dog Friendly.
Guest favorite

Home in Adams
4.92 out of 5 average rating, 59 reviewsMount Greylock View Retreat,3 bedroom,2 1/2 bath.

Farm stay in Adams
5 out of 5 average rating, 4 reviewsBerkshires/Pet Friendly farm stay w/mountain views
Top guest favorite

Apartment in Adams
4.99 out of 5 average rating, 74 reviewsCharming/Rustic Apartment with downtown views
Top guest favorite

Barn in Florida
5 out of 5 average rating, 34 reviewsThe Red Barn- close to ski mountains & museums

Home in Adams
4.93 out of 5 average rating, 247 reviews1890 House
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- Stratton Mountain
- Saratoga Race Course
- Six Flags New England
- John Boyd Thacher State Park
- Albany Center Gallery
- Jiminy Peak Mountain Resort
- Taconic State Park
- Berkshire East Mountain Resort
- Catamount Mountain Ski Resort
- Bash Bish Falls State Park
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Saratoga Spa State Park
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Norman Rockwell Museum
- Beartown State Forest
- Bright Nights at Forest Park
- Dorset Field Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Naumkeag
- Hildene, The Lincoln Family Home
- Brignole Vineyards
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