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Find All Pittsfield Hotels
We have found 1295 Pittsfield Hotels
- Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
- Historic Stone Church in The Berkshires
- Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
- Chambery Inn / 7,000 Sqft Luxury Historic Berkshire landmark on Main Street
- Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
- Modern Country Farmhouse, Walking Distance to Lake
- Seven Hills Inn
- 18th century Berkshires farmhouse on 12 acres, impeccably updated.
- Modern Victorian - 2.5hrs from NYC - 100acres - Nature- Country living
- Eastgate Inn B&B
- Charming 3-bedroom farmhouse with WiFi, central air in lovely Ghent
- Pres Week- Bentley Brook Resort - Your Peak Winter Escape
- Cranwell Spa and Golf Resort
- Xmas in Hancock @ Jiminy Premier Ski-In/Ski-Out Resort
- Eastover Estate & Eco-Village
- Doctor Sax House
- Stay Berkshires
- Lantern House Motel
- Tourists
- Renovated Private Guest House by Evergreen Home
- Hot SKI-in SKI-out Rentals Bentley Brook Resort!
- The Springs Motel
- Becket Motel
- Charming Farmhouse; 2 Bed / 2 Bath, only 1.5 miles to Jiminy Peak. Pet Friendly.
- Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss
- Castle Inn
- Garden Gables Inn
- Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - B
- Restored historic farmhouse on 25 private acres
- Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A
- Berkshire Mountain House
- Ski Jiminy Peak - Lg 1 Bd - Vacation Village in the Berkshires
- Bentley Brook, Charming 2-bedroom with WiFi, at Jiminy Peak Ski Resort
- Hampton Terrace Inn
- The Orchards Hotel
- The Red Door B&B
- Farmhouse on Otis Pond
- Private Unit in shared 1830 Farmhouse
- Guest House Sanctuary by Evergreen Home
- Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out
- Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl
- Jacob's Tanglewood Ranch
- Vacation Village In The Berkshires 5 Star Resort - Suite B
- Kemble Inn
- Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury
- Vacation Village in the Berkshires 5 Star Resort - Suite A
- Historic 1817 Berkshire Farmhouse- Close to Everything!
- Chesapeake Inn of Lenox
- Northside Motel
- Holiday Inn Club Vacations Oak 'n Spruce Resort
- Bentley Brook at Jiminy Peak ^ Studio
- Charming 6 Bdrm Countryside Stay
- Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort
- The Kemble Berkshires
- Your Winter Escape: Wyndham Bentley Brook Ski-In, Ski-Out Bliss at Jiminy Peak!"
- 10 Minutes to Ski Butternut! Dogs Welcome!
- Ladd Brook Inn
- Lenox Inn
- 67 Church Street
- Terrific 2-bedroom resort in Lee with WiFi, fitness room, AC
- Green Valley Motel
- Secluded 19th century Farmhouse with mountain views
- Barn House: isolated sheep farm Hudson area
- 26 Church Street
- Vanderbilt Lakeside
- Blue Spruce Inn & Suites
- The Weathervane Motel
- Chestnut Lodge
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires
- Mile Hill B&B
- 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.
- 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
- ONTARA....