See all 1578 hotels in Old Chatham
- Four Season Motel
- Hideaway Inn Lenox
- Club Wyndham Bentley Brook
- NEW RENO Historic Creamery in Berkshires w/hot tub
- In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
- 33 Main
- Hampton Terrace Inn
- Hudson valley and The Berkshires Cottage
- 1789 Shaker Farmhouse in Berkshires/Hudson Valley
- Charming 5-bedroom farmhouse with AC, WiFi in delightful Ghent
- Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
- Inn at Kenmore Hall
- COZY CABIN IN BERKSHIRES RESORT. SKI IN AND OUT. PET FRIENDLY.
- Modern Country Farmhouse, Walking Distance to Lake
- Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!
- Experience Timeless Elegance in The Edith Wharton Room!
- NEW RENO - Chalet-style farm loft near Tanglewood
- Farm House Getaway on beautiful horse farm!
- Enjoy the winter wonderland, ski Jiminy Peak, hot tube & explore the Berkshires
- Magic Forest Farm's Artist Retreat
- Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
- Ski at Historic Stone Church in The Berkshires
- Wagon Wheel Inn
- The Egremont Village Inn
- Apple Tree Inn
- Seven Hills Inn
- HollyKissHudsonValley Renovated 1900 Lodge, Full House, including Guest Suite
- -Private renovated farmhouse along the Hudson surrounded by State Park Land
- Vacation Village In The Berkshires 5 Star Resort - Suite B
- 1 Bd - Vacation Village in the Berkshires
- Eastgate Inn B&B
- Tranquil Retreat - Comfort and Convenience.
- Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
- Renovated Private Guest House by Evergreen Home
- HollyKissHudsonValley Fully Renovated Lodge- Private Guest Suite
- HollyKissHudsonValley Full House + Renovated Upstairs Red Barn and Loft
- Berkshire Mountain House
- Chesapeake Inn of Lenox
- Magic Forest Farm's Mountain View Suite
- Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
- Garden Gables Inn
- Eastover Estate & Eco-Village
- Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
- The Dewey
- Holiday Inn Club Vacations Oak 'n Spruce Resort
- Batterby House – Adults Only
- Elegant suite with a king bed, fireplace, and kitchenette.
- Historic Susan B. Anthony Room - Cozy & Charming Stay
- Country living close to the capital region 100 acres of nature to explore
- Castle Inn
- Jacob's Tanglewood Ranch
- Lantern House Motel
- Rustic Catskill cottage, 10 min to Hudson, 30 minutes to popular ski area skiing
- Heart of the Berkshires
- The Red Door B&B
- The Turner Farm- 3bd Historic Gem with Lush Modern Amenities and Rich History
- All the comfort of home
- 26 Church Street
- Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
- Large pool 4-bedroom farmhouse in Hudson with Mountain View’s pet friendly
- "Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
- The Kemble Berkshires
- Charming 6 Bdrm Countryside Stay
- 1735 Stone Farmhouse
- Historic farmhouse w/ private Catskill Creek access. Close to skiing and hiking.
- Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
- Hot SKI-in SKI-out Rentals Bentley Brook Resort!
- Blue Spruce Inn & Suites
- Elegant Carriage House room with a queen bed and private patio.
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