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Find All Chatham Hotels
We have found 1571 Chatham Hotels
- Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!
- Farm House Getaway on 200 acre horse farm!
- Eastgate Inn B&B
- Lantern House Motel
- Lenox Inn
- In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
- -Private renovated farmhouse along the Hudson surrounded by State Park Land
- Heart of the Berkshires
- Berkshire Mountain House
- LEEDS A GREAT ESCAPE
- Bentley Brook the perfect home base for exploring nearby Berkshire County
- Country living close to the capital region 100 acres of nature to explore
- Experience Timeless Elegance in The Edith Wharton Room!
- Race Brook Lodge
- Cranwell Spa and Golf Resort
- Berkshire Rural Retreat
- Charming 6 Bdrm Countryside Stay
- New 4500 sq ft modern 5 bed-5.5 bath on Housatonic River and walk to Stockbridge
- Restored historic farmhouse on 25 private acres
- Garden Gables Inn
- Bentley Brook the perfect home base for exploring nearby Berkshire County
- Eastover Estate & Eco-Village
- HollyKissHudsonValley Renovated 1900 Lodge, Full House, including Guest Suite
- Hampton Terrace Inn
- 26 Church Street
- Bentley Brook the perfect home base for exploring nearby Berkshire County
- Doctor Sax House
- Modern Country Farmhouse, Walking Distance to Lake
- The Dewey
- Elegant suite with a king bed, fireplace, and kitchenette.
- Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
- The Grange - 1800s Farmhouse Estate on 80 Acres
- Kemble Inn
- Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
- Holiday Inn Club Vacations Oak 'n Spruce Resort
- All the comfort of home
- HollyKissHudsonValley Fully Renovated Lodge- Private Guest Suite
- Jacob's Tanglewood Ranch
- 67 Church Street
- "Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
- Historic Susan B. Anthony Room - Cozy & Charming Stay
- Lg 1 Bd - Vacation Village in the Berkshires
- Private Unit in shared 1830 Farmhouse
- COZY CABIN IN BERKSHIRES RESORT - LABOR DAY SALE
- The Red Door B&B
- Castle Inn
- Elegant Carriage House room with a queen bed and private patio.
- Chesapeake Inn of Lenox
- Renovated Private Guest House by Evergreen Home
- HollyKissHudsonValley Full House + Renovated Upstairs Red Barn and Loft
- Cliffwood Cottage by Evergreen Home
- 1805 House Bed and Breakfast
- Cozy Carriage House room with a double bed and private balcony
- Batterby House – Adults Only
- The Whitlock
- Spacious Modern Catskill Farmhouse - Hot Tub, Pool, Fire-Pit, Views
- Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out
- Rustic Catskill cottage, 10 min to Hudson, 30 minutes to popular ski area skiing
- Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
- Charming Farmhouse; 2 Bed / 2 Bath, only 1.5 miles to Jiminy Peak. Pet Friendly.
- The Kemble Berkshires
- Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
- 1735 Stone Farmhouse
- Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A
- Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss
- Vacation Village In The Berkshires 5 Star Resort - Suite B
- Hudson City Bed & Breakfast
- Historic 1817 Berkshire Farmhouse- Close to Everything!
- Jiminy Premier Ski-In/Ski-Out Resort Bentley B
- Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl
- Inn at 34
- Terrific 2-bedroom resort in Lee with WiFi, fitness room, AC
- Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury
- Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
- Bentley Brook: Ultimate Ski-In Ski-Out -Crazy