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Compare 89 Cottages in Chester with updated reviews, rates, and availability.

The Clearing - Quiet - Close To Nature
The Clearing - Quiet - Close To Nature
10.0 out of 10, Exceptional, (187)

Quiet rustic cottage with shared lake access
Quiet rustic cottage with shared lake access
10.0 out of 10, Exceptional, (104)

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
9.2 out of 10, Wonderful, (11)

East Otis Vacation Rental w/ Private Deck & BBQ!
East Otis Vacation Rental w/ Private Deck & BBQ!
9.6 out of 10, Exceptional, (7)

Family-Friendly Richmond Cottage w/ Private Yard
Family-Friendly Richmond Cottage w/ Private Yard
10.0 out of 10, Exceptional, (4)

Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
10.0 out of 10, Exceptional, (3)

Massachusetts Vacation Rental w/ Deck
Massachusetts Vacation Rental w/ Deck

Private Island - Largest Fresh Water Reservoir in Mass....
Private Island - Largest Fresh Water Reservoir in Mass....
9.0 out of 10, Wonderful, (7)
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.
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Other property types in Chester

The Ponds at Foxhollow
The Ponds at Foxhollow
8.6 out of 10, Excellent, (120)
The price is SARĀ 841
SARĀ 940 total
includes taxes & fees
9 May - 10 May

Deluxe Queen Room with 2 Queen Beds
Deluxe Queen Room with 2 Queen Beds
The price is SARĀ 409
SARĀ 541 total
includes taxes & fees
28 Apr - 29 Apr

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
9.4 out of 10, Exceptional, (61)
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.
Recent reviews of Chester hotels
Recent reviews of Chester hotels

The Black Swan Lee - Lenox, Ascend Hotel Collection
5/5 Excellent
Great stay
"Clean, comfortable and quiet. Stay here frequently. Very friendly front desk. "
A verified traveler stayed at The Black Swan Lee - Lenox, Ascend Hotel Collection
Posted 7 hours ago