Top Chester Holiday Cottages in 2025
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Featured Cottages in Chester

The Clearing - Quiet - Close To Nature
Our customers tell us that they can't get enough of the overall property condition at this cottage. During your stay, you're just a quick walk from Westfield River. An outdoor pool is available. Enjoy your stay with amenities like free WiFi and a private pool in the cottage.
Pool
Kitchen

Quiet rustic cottage with shared lake access
During your stay at this cottage, you're just a quick walk from Lake Buel. The cottage includes amenities such as a fireplace and a patio.
Washer
Dryer

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
During your stay at this cottage, you're just a quick walk from Lake Buel. Enjoy your stay with amenities like free WiFi and a kitchen in the cottage.
Kitchen
Washer

East Otis Vacation Rental w/ Private Deck & BBQ!
During your stay at this cottage, you're just a quick walk from Otis Reservoir. The cottage includes amenities such as a kitchen and a fireplace.
Kitchen
Outdoor space

Family-Friendly Richmond Cottage w/ Private Yard
During your stay at this cottage, you'll be within walking distance of Nordeen Marsh Natural Heritage Area. The cottage includes amenities such as a kitchen and 2 bathrooms.
Kitchen
Washer

Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
During your stay at this cottage, you'll be close to Bidwell House Museum. Enjoy your stay with amenities like a kitchen and a fireplace in the cottage.
Kitchen
Washer

Massachusetts Vacation Rental w/ Deck
During your stay at this cottage, you'll be close to Lyman Conservatory. Enjoy features like free WiFi in public areas and free self-parking, plus an arcade/games room. The cottage offers a kitchen and a TV.
Kitchen
Pet-friendly

Private Island - Largest Fresh Water Reservoir in Mass....
During your stay at this cottage, you're just a quick walk from Otis Reservoir. The cottage includes amenities such as free WiFi and a kitchen.
Kitchen
Pet-friendly

Charming historic cottage on scenic road to Mt. Greylock
During your stay at this cottage, you'll be within walking distance of Mount Greylock State Reservation. Free WiFi in public areas is available. The cottage offers free WiFi and a kitchen.
Kitchen
Free WiFi

Beachwood Cottage
During your stay at this cottage, you'll be close to Tanglewood Music Center. The cottage includes amenities such as free WiFi and a kitchen.
Kitchen
Washer

4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!
During your stay at this cottage, you're just a quick walk from Nordeen Marsh Natural Heritage Area. The cottage offers a kitchen and 2 bathrooms.
Kitchen
Washer

Lake Views & Dock Access - Pittsfield Cottage!
During your stay at this cottage, you'll be close to Jiminy Peak Mountain Resort. A kitchen and 1.5 bathrooms are available in the cottage.
Kitchen
Washer

Private Lake Cottage on 3 acres w/350 sq. ft. deck
During your stay at this cottage, you'll be within walking distance of Iroquis Waterfront. Enjoy your stay with amenities like 2 bathrooms and a washing machine in the cottage.
Washer
Dryer

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
During your stay at this cottage, you're just a quick walk from Lake Buel. The cottage offers a kitchen and a washer/dryer.
Kitchen
Washer
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Chester Cottages essential information
Accommodation | 87 Cottages |
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Lowest Price | |
Highest Price | |
Popular accommodation | The Clearing - Quiet - Close To Nature, Quiet rustic cottage with shared lake access, Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly! , East Otis Vacation Rental w/ Private Deck & BBQ!, Family-Friendly Richmond Cottage w/ Private Yard, Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks, Massachusetts Vacation Rental w/ Deck, Private Island - Largest Fresh Water Reservoir in Mass...., Charming historic cottage on scenic road to Mt. Greylock, Beachwood Cottage, 4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!, Lake Views & Dock Access - Pittsfield Cottage!, Private Lake Cottage on 3 acres w/350 sq. ft. deck , Rustic Berkshires Cottage at Lake Buel w/ Kayaks!, 1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge |
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