
Holiday rentals in Chester
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Top-rated holiday rentals in Chester
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Popular amenities for Chester holiday rentals
Other great holiday rentals in Chester
Guest favourite

Cabin in Williamsburg
4.94 out of 5 average rating, 35 reviewsRetreat in the Woods

Cabin in Otis
4.81 out of 5 average rating, 21 reviewsSimple, rustic, cozy get away
Top guest favourite

Farm stay in Blandford
5 out of 5 average rating, 41 reviewsFreeland Brook Farm - stunning Berkshires view

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

Home in Becket
4.96 out of 5 average rating, 28 reviewsNew Shaw Pond Skytop Retreat in the Berkshires
Top guest favourite

Home in Chester
4.97 out of 5 average rating, 351 reviewsRiverfront Getaway
Top guest favourite

Cabin in Becket
4.98 out of 5 average rating, 44 reviewsEntire Private Log Cabin in the Berkshires
Guest favourite

Cottage in Great Barrington
4.94 out of 5 average rating, 137 reviewsThe Cottage at The Barrington House
Destinations to explore
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- Six Flags New England
- TPC River Highlands
- Taconic State Park
- Bushnell Park
- Berkshire East Mountain Resort
- Albany Center Gallery
- Jiminy Peak Mountain Resort
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Kent Falls State Park
- Norman Rockwell Museum
- Brimfield State Forest
- Catamount Mountain Ski Resort
- Dinosaur State Park
- Mount Snow Ski Resort
- Mohawk Mountain Ski Area
- Beartown State Forest
- Wintonbury Hills Golf Course
- Talcott Mountain State Park
- Hartford Golf Club
- Mount Sugarloaf State Reservation
- Bousquet Mountain Ski Area
- Mount Southington Ski Area
- Bright Nights at Forest Park