Chesterfield Cottages

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Cottages in Chesterfield

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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.

Chesterfield Cottages essential information

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40 Cottages
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Private Island - Largest Fresh Water Reservoir in Mass...., East Otis Vacation Rental w/ Private Deck & BBQ!, Charming historic cottage on scenic road to Mt. Greylock, Massachusetts Vacation Rental w/ Deck, Lake Views & Dock Access - Pittsfield Cottage!, Hawley Home w/ Deck: 4 Mi to Berkshire East Resort, Spacious Historic Home in the Berkshires!, Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!, Charlemont Retreat on Chickley River w/ EV Charger, Picturesque Cottage with Sunroom on Ashmere Lake!, Historic Huntington Home - Walk to Westfield River, Private Lake Cottage on 3 acres w/350 sq. ft. deck