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Find All Pittsfield Hotels
We have found 1344 Pittsfield Hotels
- Modern Country Farmhouse, Walking Distance to Lake
- COZY CABIN IN BERKSHIRES RESORT. SKI IN AND OUT. PET FRIENDLY.
- Experience Timeless Elegance in The Edith Wharton Room!
- Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!
- NEW RENO - Chalet-style farm loft near Tanglewood
- Farm House Getaway on beautiful horse farm!
- Sunset Inn
- Enjoy the winter wonderland, ski Jiminy Peak, hot tube & explore the Berkshires
- Scribe`s Stable | A/C • Screened in Porch • Sleeps 6
- Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
- Becket Motel
- Vacation Village In The Berkshires 5 Star Resort - Suite B
- Seven Hills Inn
- 1 Bd - Vacation Village in the Berkshires
- Wagon Wheel Inn
- Eastgate Inn B&B
- The Egremont Village Inn
- Chesapeake Inn of Lenox
- Renovated Private Guest House by Evergreen Home
- The Orchards Hotel
- Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
- Garden Gables Inn
- Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
- Berkshire Mountain House
- Holiday Inn Club Vacations Oak 'n Spruce Resort
- Eastover Estate & Eco-Village
- Elegant suite with a king bed, fireplace, and kitchenette.
- Historic Susan B. Anthony Room - Cozy & Charming Stay
- The Dewey
- Jacob's Tanglewood Ranch
- Lantern House Motel
- Stay Berkshires
- Private Unit in shared 1830 Farmhouse
- Country living close to the capital region 100 acres of nature to explore
- Northside Motel
- Green Valley Motel
- 26 Church Street
- Castle Inn
- "Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
- The Kemble Berkshires
- Charming 6 Bdrm Countryside Stay
- Elegant Carriage House room with a queen bed and private patio.
- Blue Spruce Inn & Suites
- Cozy Carriage House room with a double bed and private balcony
- Terrific 2-bedroom resort in Lee with WiFi, fitness room, AC
- Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
- Your Winter Escape: Wyndham Bentley Brook Ski-In
- Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
- Hot SKI-in SKI-out Rentals Bentley Brook Resort!
- Farmhouse on Otis Pond
- Jiminy Premier Ski-In/Ski-Out Resort Bentley B
- Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
- Kemble Inn
- Pres Week- Bentley Brook Resort - Your Peak Winter Escape
- 18th century Berkshires farmhouse on 12 acres, impeccably updated.
- Cliffwood Cottage by Evergreen Home
- Chestnut Lodge
- Welcome to Holiday Inn Club Vacations Oak 'n Spruce Resort, South Lee, MA
- Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury
- 67 Church Street
- Ladd Brook Inn
- Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort
- Welcome to Holiday Inn Club Vacations Oak 'n Spruce Resort, South Lee, MA
- Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss