Windsor Cottages

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Cottages in Windsor

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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.

Windsor Cottages essential information

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55 Cottages
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Charming historic cottage on scenic road to Mt. Greylock, Cozy Berkshire cottage with fireplace., Lake Views & Dock Access - Pittsfield Cottage!, Beachwood 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, Cottage in the Clouds With Mountain Views, Picturesque Cottage with Sunroom on Ashmere Lake!, Stockbridge Home: Walk to Town Beach!, Historic Huntington Home - Walk to Westfield River