See all 1595 hotels in Chatham
- NEW RENO - Chalet-style farm loft near Tanglewood
- 1789 Shaker Farmhouse in Berkshires/Hudson Valley
- Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
- COZY CABIN IN BERKSHIRES RESORT. SKI IN AND OUT. PET FRIENDLY.
- Charming 5-bedroom farmhouse with AC, WiFi in delightful Ghent
- Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
- Bentley Brook the perfect home base for exploring nearby Berkshire County
- Hudson Valley Dream Farmhouse: Bike Trails, Wineries, Five Acres
- A Writer's Retreat at The Barn
- Farmhouse Retreat, Outdoor Dining/Fire-Pit, Fast Wifi, Golf & 3-Acre Privacy
- Experience Timeless Elegance in The Edith Wharton Room!
- Copper Kettle Farm - newly renovated farmhouse with spectacular views
- Monk's Bunk, Old Chatham
- Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
- Historic Susan B. Anthony Room - Cozy & Charming Stay
- Cozy Carriage House room with a double bed and private balcony
- Bentley Brook the perfect home base for exploring nearby Berkshire County
- Bentley Brook the perfect home base for exploring nearby Berkshire County
- Farm House Getaway on beautiful horse farm!
- "Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
- Charming 6 Bdrm Countryside Stay
- HollyKissHudsonValley Full House + Renovated Upstairs Red Barn and Loft
- Come to our lake house, pick apples, kayak & enjoy the fall foliage.
- Elegant Carriage House room with a queen bed and private patio.
- 1 Bd - Vacation Village in the Berkshires
- Elegant suite with a king bed, fireplace, and kitchenette.
- Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
- Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
- Heart of the Berkshires
- Berkshire Mountain Lodge
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