See all 1580 hotels in Chatham
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
- Pocketbook Hotel and Bath
- Prospect Berkshires
- Element Lenox Berkshires
- Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
- The Whitlock
- The Wick, Hudson, A Tribute Portfolio Hotel
- Spark by Hilton West Coxsackie
- Howard Hotel
- Hudson Navigator
- Gregory House Country Inn
- Club Wyndham Bentley Brook
- 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
- Charming 5-bedroom farmhouse with AC, WiFi in delightful Ghent
- COZY CABIN IN BERKSHIRES RESORT. SKI IN AND OUT. PET FRIENDLY.
- NEW RENO - Chalet-style farm loft near Tanglewood