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Find All Pittsfield Hotels
We have found 1319 Pittsfield Hotels
- Farm House Getaway on 200 acre horse farm!
- In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
- Modern Country Farmhouse, Walking Distance to Lake
- SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires!
- Berkshire Rural Retreat
- Cranwell Spa and Golf Resort
- Stay Berkshires
- Bentley Brook the perfect home base for exploring nearby Berkshire County
- Eastover Estate & Eco-Village
- Hampton Terrace Inn
- Modern Victorian - 2.5hrs from NYC - 100acres - Nature- Country living
- Bentley Brook the perfect home base for exploring nearby Berkshire County
- 18th century Berkshires farmhouse on 12 acres, impeccably updated.
- Doctor Sax House
- Restored historic farmhouse on 25 private acres
- Kemble Inn
- Bentley Brook the perfect home base for exploring nearby Berkshire County
- Charming Farmhouse; 2 Bed / 2 Bath, only 1.5 miles to Jiminy Peak. Pet Friendly.
- Ski Jiminy Peak - Lg 1 Bd - Vacation Village in the Berkshires
- Castle Inn
- Lantern House Motel
- Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out
- Renovated Private Guest House by Evergreen Home
- The Red Door B&B
- Private Unit in shared 1830 Farmhouse
- Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
- Holiday Inn Club Vacations Oak 'n Spruce Resort
- Lenox Inn
- The Orchards Hotel
- 67 Church Street
- Vacation Village In The Berkshires 5 Star Resort - Suite B
- Guest House Sanctuary by Evergreen Home
- Northside Motel
- 26 Church Street
- Berkshire Mountain House
- Jacob's Tanglewood Ranch
- Tourists
- Charming 6 Bdrm Countryside Stay
- Chesapeake Inn of Lenox
- Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl
- Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
- Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss
- Farmhouse on Otis Pond
- Jiminy Premier Ski-In/Ski-Out Resort Bentley B
- Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A
- Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
- Bentley Brook, Charming 2-bedroom with WiFi, at Jiminy Peak Ski Resort
- Historic 1817 Berkshire Farmhouse- Close to Everything!
- 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
- Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort
- Hot SKI-in SKI-out Rentals Bentley Brook Resort!
- Vacation Village in the Berkshires 5 Star Resort - Suite A
- Cliffwood Cottage by Evergreen Home
- The Revival House
- Green Valley Motel
- Garden Gables Inn
- Secluded 19th century Farmhouse with mountain views
- Ladd Brook Inn
- Vanderbilt Lakeside
- The Weathervane Motel
- Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - B
- 10 Minutes to Ski Butternut! Dogs Welcome!
- Terrific 2-bedroom resort in Lee with WiFi, fitness room, AC
- Canyon Ranch Lenox
- Renovated Berkshires Farmhouse - minutes from hiking, swimming, and Tanglewood
- Cozy and large 2 Bedroom 2 Full Bath ski in, ski out condo Unit with balcony.
- Your Winter Escape: Wyndham Bentley Brook Ski-In, Ski-Out Bliss at Jiminy Peak!"
- Bentley Brook 1-BR Mountainside resort sleeps 8- Available April 27-May 3
- Charming 2-bedroom resort in marvelous Hancock with AC, fitness room, WiFi
- Cozy 1-bedroom at a New England style resort in the Berkshire mountains
- Chestnut Lodge
- ONTARA....
- Oak n' Spruce Resort in the Berkshires. Charming 2-bedroom in quaint Lee