Top Chester Holiday Cottages in 2025

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Featured Cottages in Chester

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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

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87 Cottages
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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