All hotels in Pittsfield, Massachusetts
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
All hotels in Pittsfield, Massachusetts
We have found 1296 Pittsfield Hotels
- Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
- Chambery Inn / 7,000 Sqft Luxury Historic Berkshire landmark on Main Street
- 18th century Berkshires farmhouse on 12 acres, impeccably updated.
- Modern Country Farmhouse, Walking Distance to Lake
- Modern Victorian - 2.5hrs from NYC - 100acres - Nature- Country living
- Seven Hills Inn
- Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
- Eastover Estate & Eco-Village
- Hot SKI-in SKI-out Rentals Bentley Brook Resort!
- Ski Jiminy Peak - Lg 1 Bd - Vacation Village in the Berkshires
- Stay Berkshires
- Lantern House Motel
- Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - B
- Guest House Sanctuary by Evergreen Home
- Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury
- Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A
- Xmas in Hancock @ Jiminy Premier Ski-In/Ski-Out Resort
- Garden Gables Inn
- Farmhouse on Otis Pond
- Hampton Terrace Inn
- Restored historic farmhouse on 25 private acres
- Private Unit in shared 1830 Farmhouse
- Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out
- Bentley Brook, Charming 2-bedroom with WiFi, at Jiminy Peak Ski Resort
- The Red Door B&B
- Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss
- Pres Week- Bentley Brook Resort - Your Peak Winter Escape
- Jacob's Tanglewood Ranch
- Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl
- Northside Motel
- Holiday Inn Club Vacations Oak 'n Spruce Resort
- Bentley Brook at Jiminy Peak ^ Studio
- Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort
- 10 Minutes to Ski Butternut! Dogs Welcome!
- Lenox Inn
- Your Winter Escape: Wyndham Bentley Brook Ski-In, Ski-Out Bliss at Jiminy Peak!"
- Terrific 2-bedroom resort in Lee with WiFi, fitness room, AC
- Green Valley Motel
- Blue Spruce Inn & Suites
- Chestnut Lodge
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires
- 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.
- Cozy 1-bedroom at a New England style resort in the Berkshire mountains
Let Expedia take you to the best Hotels in Pittsfield. You'll find the largest selection of hotel deals, discount prices, and cheap hotel rates on reservations anywhere in the world. Expedia, the leader in world travel, gives you customer reviews, maps, and the best selection of hotels near landmarks and attractions.