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 1009 Cheshire Hotels
- Harbour House Inn
- The Williams Inn
- Berkshires Untold
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
- Holiday Inn & Suites Pittsfield-Berkshires by IHG
- The Yankee, Trademark Collection by Wyndham
- The Red Lion Inn
- The Constance by the Lenox Collection
- Berkshire Mountain Lodge
- Hampton Inn & Suites Berkshires-Lenox
- The Black Swan Lee - Lenox, Ascend Hotel Collection
- Hotel On North
- The Whitlock
- Berkshire Inn
- Fairfield Inn & Suites by Marriott Williamstown
- The Villager Motel
- Cozy Corner Motel
- The Cornell Inn, Lenox & The Berkshires
- The Porches Inn at Mass MoCA
- Williamstown Motel
- Gregory House Country Inn
- Berkshire Travel Lodge
- The Springs Motel
- Chambery Inn
- Blooming Inn
- Berkshire Valley Inn
- 1896 House Country Inn & Motels
- Tanglewood Suites
- The Central Downtown Inn & Suites
- Inn at Silver Maple Farm
- Whistler's Inn Bed & Breakfast
- Holiday Inn Express & Suites Pittsfield - Berkshires
- Apple Tree Inn
- Shaker Mill Inn
- Devonfield Inn B&B
- The Trail in Adams - Berkshires’ Art Hotel
- Starlight Inn
- Gateways Inn & Restaurant
- The Orchards Hotel
- Seven Hills Inn
- Holiday Inn Club Vacations Oak 'n Spruce Resort
- The Inn at Stockbridge
- Eastover Estate & Eco-Village
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.