
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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Popular amenities for Chester holiday rentals
Other great holiday rentals in Chester
Top guest favourite

Home in Hinsdale
5 out of 5 average rating, 7 reviewsBerkshire Lake-side Retreat
Top guest favourite

Private room in Northampton
4.95 out of 5 average rating, 812 reviewsWarm Country Home Mins. from Town
Guest favourite

Private room in Agawam
4.86 out of 5 average rating, 282 reviewsHampden Room

Cottage in Otis
4.89 out of 5 average rating, 18 reviewsCozy Cottage in the Berkshires

Home in Tolland
5 out of 5 average rating, 4 reviewsCabin with Hot Tub and Lake Access
Top guest favourite

Private room in Becket
4.86 out of 5 average rating, 235 reviewsEast b.r. in upstairs suite of open plan home
Guest favourite

Home in Washington
4.93 out of 5 average rating, 15 reviewsPeaceful Retreat in the Berkshires
Guest favourite

Cabin in Becket
4.89 out of 5 average rating, 28 reviewsCozy Cottage in the Woods
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
- Talcott Mountain State Park
- Bright Nights at Forest Park
- Albany Center Gallery
- Bousquet Mountain Ski Area