
Holiday rentals in Chester
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Top-rated holiday rentals in Chester
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Chester holiday rentals
Other great holiday rentals in Chester
Guest favourite

Home in Becket
4.94 out of 5 average rating, 126 reviewsBeautiful, quiet and cozy home in Becket!
Guest favourite

Home in Washington
5 out of 5 average rating, 24 reviewsModern Berkshire Mountain Home
Guest favourite

Home in Becket
4.97 out of 5 average rating, 86 reviewsNerd Preservation Sanctuary
Guest favourite

Cabin in Chester
4.96 out of 5 average rating, 56 reviews2 Rustic Cabins on 68 Secluded Acres
Guest favourite

Home in Becket
4.93 out of 5 average rating, 81 reviewsLittle Longbow Lakefront Chalet
Guest favourite

Home in Becket
4.91 out of 5 average rating, 43 reviewsPristine Home In Becket Woods
Guest favourite

Home in Ashfield
4.97 out of 5 average rating, 71 reviewsAn 18th century farmhouse
Top guest favourite

Guest house in Lanesborough
5 out of 5 average rating, 9 reviewsThe Carriage House: Spotless, Charming 2 Bedroom
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- Mount Pocono Holiday rentals
- South Jersey Holiday rentals
- The Hamptons Holiday rentals
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- TPC River Highlands
- Bash Bish Falls State Park
- Bushnell Park
- Kent Falls State Park
- Brimfield State Forest
- Catamount Mountain Ski Resort
- Mount Greylock Ski Club
- Wintonbury Hills Golf Course
- Norman Rockwell Museum
- Bigelow Hollow State Park
- Taconic State Park
- Dinosaur State Park
- Mount Sugarloaf State Reservation
- Mount Southington Ski Area
- Mount Tom State Reservation
- Mohawk Mountain Ski Area
- Beartown State Forest
- Albany Center Gallery
- Talcott Mountain State Park
- Bright Nights at Forest Park
- Bousquet Mountain Ski Area