Photo by Ed Gaffny

Featured Inns in Cheshire

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Stay at this 3-star inn in Averill Park. Enjoy free WiFi, free parking, and daily housekeeping. Popular attraction Pineridge Cross Country Ski Center is located ...

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Stay at this inn in Williamstown. Enjoy free parking, a business center, and a garden. Popular attractions Sheep Hill and Bullock Ledge Wildlife Management Area ...

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Stay at this 3-star inn in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...

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Stay at this 3.5-star boutique inn in Lenox. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Ventfort Hall ...

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Stay at this inn in Lenox. Enjoy free WiFi, free parking, and a garden. Popular attractions Tanglewood Music Center and Ventfort Hall Mansion and Gilded Age ...

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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.

Can't find what you're looking for? Check out these other accommodation options...

Hotel Downstreet, Ascend Hotel Collection

40 Main St, North Adams, MA

Life House Berkshires

194 Pittsfield Rd, Lenox, MA

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.