See all 1318 hotels in Pittsfield
- Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
- Heart of the Berkshires
- Berkshire Mountain Lodge
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
- Prospect Berkshires
- Element Lenox Berkshires
- The Whitlock
- Gregory House Country Inn
- Club Wyndham Bentley Brook
- The Springs Motel
- The Orchards Hotel
- The Revival House
- 1800s Carriage house in Berkshires / Hudson Valley
- Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
- NEW RENO - Historic Loft w/views of the Berkshires
- The Dewey
- Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
- NEW RENO Historic Creamery in Berkshires w/hot tub
- Experience Timeless Elegance in The Edith Wharton Room!
- Harbour House Inn
- COZY CABIN IN BERKSHIRES RESORT. SKI IN AND OUT. PET FRIENDLY.