See all 1580 hotels in Chatham
- 1789 Shaker Farmhouse in Berkshires/Hudson Valley
- NEW RENO Historic Creamery in Berkshires w/hot tub
- Experience Timeless Elegance in The Edith Wharton Room!
- Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
- Come to our lake house, pick apples, kayak & enjoy the fall foliage.
- Farmhouse Retreat, Outdoor Dining/Fire-Pit, Fast Wifi, Golf & 3-Acre Privacy
- 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!
- 1 Bd - Vacation Village in the Berkshires
- HollyKissHudsonValley Full House + Renovated Upstairs Red Barn and Loft
- A Writer's Retreat at The Barn
- Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
- Monk's Bunk, Old Chatham
- Historic Susan B. Anthony Room - Cozy & Charming Stay
- Elegant suite with a king bed, fireplace, and kitchenette.
- Bentley Brook the perfect home base for exploring nearby Berkshire County
- "Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
- Heart of the Berkshires
- Cozy Carriage House room with a double bed and private balcony
- Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
- Charming 6 Bdrm Countryside Stay
- Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
- Elegant Carriage House room with a queen bed and private patio.
- Cliffwood Cottage by Evergreen Home