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