See all 985 hotels in Cheshire
- Harbour House Inn
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
- Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
- Element Lenox Berkshires
- The Springs Motel
- The Whitlock
- Club Wyndham Bentley Brook
- The Revival House
- The Dewey
- Gregory House Country Inn
- NEW RENO Historic Creamery in Berkshires w/hot tub
- NEW RENO - Historic Loft w/views of the Berkshires
- The Orchards Hotel
- 1800s Carriage house in Berkshires / Hudson Valley
- In town, newly remodeled studio with private balcony
- NEW RENO - Chalet-style farm loft near Tanglewood
- Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
- 1789 Shaker Farmhouse in Berkshires/Hudson Valley
- COZY CABIN IN BERKSHIRES RESORT. SKI IN AND OUT. PET FRIENDLY.
- Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
- Bentley Brook the perfect home base for exploring nearby Berkshire County