Photo by Ed Gaffny
All hotels in Cheshire, Massachusetts
Change your mind
Book hotels with free cancellation
Be picky
Search almost a million properties worldwide
All hotels in Cheshire, Massachusetts
We have found 997 Cheshire Hotels
- Harbour House Inn
- Berkshire Mountain Lodge
- Berkshires Untold
- The Williams Inn
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
- The Red Lion Inn
- The Yankee, Trademark Collection by Wyndham
- Holiday Inn & Suites Pittsfield-Berkshires by IHG
- Hampton Inn & Suites Berkshires-Lenox
- The Constance by the Lenox Collection
- The Black Swan Lee - Lenox, Ascend Hotel Collection
- Hotel On North
- The Springs Motel
- Fairfield Inn & Suites by Marriott Williamstown
- Holiday Inn Express & Suites Pittsfield - Berkshires
- Berkshire Inn
- The Whitlock
- Cozy Corner Motel
- The Villager Motel
- The Cornell Inn, Lenox & The Berkshires
- The Porches Inn at Mass MoCA
- Williamstown Motel
- Blooming Inn
- The Dewey
- The Central Downtown Inn & Suites
- Berkshire Travel Lodge
- The Revival House
- Element Lenox Berkshires
- Apple Tree Inn
- Gregory House Country Inn
- Chambery Inn
- Tanglewood Suites
- Inn at Silver Maple Farm
- Whistler's Inn Bed & Breakfast
- Berkshire Valley Inn
- 1896 House Country Inn & Motels
- Starlight Inn
- Devonfield Inn B&B
- The Trail in Adams - Berkshires’ Art Hotel
- Shaker Mill Inn
- Hampton Terrace Inn
- Gateways Inn & Restaurant
- The Orchards Hotel
- Seven Hills Inn
- Holiday Inn Club Vacations Oak 'n Spruce Resort
- Eastover Estate & Eco-Village
- The Inn at Stockbridge
Let Expedia take you to the best Hotels in Cheshire. 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.