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Compare 75 Cottages in Chester with updated reviews, rates, and availability.
Private Island - Largest Fresh Water Reservoir in Mass....
Private Island - Largest Fresh Water Reservoir in Mass....
9.0 out of 10, Wonderful, (7)
East Otis Vacation Rental w/ Private Deck & BBQ!
East Otis Vacation Rental w/ Private Deck & BBQ!
9.6 out of 10, Exceptional, (7)
Charming historic cottage on scenic road to Mt. Greylock
Charming historic cottage on scenic road to Mt. Greylock
10.0 out of 10, Exceptional, (104)
Cozy Berkshire cottage with fireplace.
Cozy Berkshire cottage with fireplace.
10.0 out of 10, Exceptional, (22)
Massachusetts Vacation Rental w/ Deck
Massachusetts Vacation Rental w/ Deck
Private Lake Cottage on 3 acres w/350 sq. ft. deck
Private Lake Cottage on 3 acres w/350 sq. ft. deck
Perfect Vacation Get Away - Historical New Marlborough
Perfect Vacation Get Away - Historical New Marlborough
9.4 out of 10, Exceptional, (54)
The Clearing - Quiet - Close To Nature
The Clearing - Quiet - Close To Nature
10.0 out of 10, Exceptional, (187)
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
Cozy Berkshires Vacation Rental Near Hiking!
Cozy Berkshires Vacation Rental Near Hiking!
10.0 out of 10, Exceptional, (1)
Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (232)
The price is SAR 548
SAR 839 total
includes taxes & fees
30 Dec - 31 Dec
Peace and quiet on the lake
Peace and quiet on the lake
9.6 out of 10, Exceptional, (200)
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
5/5 Excellent
"The hotel was great! The attached AMAZING Indian restaurant was an unexpected treat! "
A verified traveler from Harwich stayed at The Black Swan Lee - Lenox, Ascend Hotel Collection
Posted 19 hours ago