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Find All Pittsfield Hotels
We have found 1349 Pittsfield Hotels
- Historic Stone Church in The Berkshires
- Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!
- Bentley Brook the perfect home base for exploring nearby Berkshire County
- Bentley Brook the perfect home base for exploring nearby Berkshire County
- Cranwell Spa and Golf Resort
- Restored historic farmhouse on 25 private acres
- Berkshire Rural Retreat
- Garden Gables Inn
- In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
- Bentley Brook the perfect home base for exploring nearby Berkshire County
- Eastover Estate & Eco-Village
- Prospect Berkshires
- Hampton Terrace Inn
- Lantern House Motel
- The Orchards Hotel
- Lenox Inn
- Doctor Sax House
- Berkshire Mountain House
- Elegant suite with a king bed
- Historic Cornell Inn - Cozy Berkshires Retreat - Lenox
- 18th century Berkshires farmhouse on 12 acres, impeccably updated.
- Modern Victorian - 2.5hrs from NYC - 100acres - Nature- Country living
- Kemble Inn
- New 4500 sq ft modern 5 bed-5.5 bath on Housatonic River and walk to Stockbridge
- Holiday Inn Club Vacations Oak 'n Spruce Resort
- 26 Church Street
- Stay Berkshires
- Jacob's Tanglewood Ranch
- Experience Timeless Elegance in The Edith Wharton Room!
- Historic Susan B. Anthony Room - Cozy & Charming Stay
- 67 Church Street
- Charming 6 Bdrm Countryside Stay
- Tourists
- The Dewey
- SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires!
- Private Unit in shared 1830 Farmhouse
- The Red Door B&B
- Castle Inn
- Modern Country Farmhouse, Walking Distance to Lake
- Green Valley Motel
- Ski Jiminy Peak - Lg 1 Bd - Vacation Village in the Berkshires
- Cozy Carriage House room with a double bed and private balcony
- Cliffwood Cottage by Evergreen Home
- Chesapeake Inn of Lenox
- Renovated Private Guest House by Evergreen Home
- Northside Motel
- Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
- Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
- Charming Farmhouse; 2 Bed / 2 Bath, only 1.5 miles to Jiminy Peak. Pet Friendly.
- Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out
- Historic 1817 Berkshire Farmhouse- Close to Everything!
- Oak n' Spruce Resort in the Berkshires. Charming 2-bedroom in quaint Lee
- The Whitlock
- Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss
- Vacation Village In The Berkshires 5 Star Resort - Suite B
- Guest House Sanctuary by Evergreen Home
- Farmhouse on Otis Pond
- Ladd Brook Inn
- Jiminy Premier Ski-In/Ski-Out Resort Bentley B
- Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl
- Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A
- The Kemble Berkshires
- Bentley Brook at Jiminy Peak ^ Studio
- Pres Week- Bentley Brook Resort - Your Peak Winter Escape
- 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
- Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort
- Hot SKI-in SKI-out Rentals Bentley Brook Resort!
- Bentley Brook, Charming 2-bedroom with WiFi, at Jiminy Peak Ski Resort
- Elegant Carriage House room with a queen bed and private patio.
- Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
- Terrific 2-bedroom resort in Lee with WiFi, fitness room, AC
- Secluded 19th century Farmhouse with mountain views
- The Weathervane Motel
- Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
- Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - B
- 10 Minutes to Ski Butternut! Dogs Welcome!
- Your Winter Escape: Wyndham Bentley Brook Ski-In, Ski-Out Bliss at Jiminy Peak!"
- ONTARA....
- Canyon Ranch Lenox