Photo by Ed Gaffny
All hotels in Cheshire, 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 Cheshire, Massachusetts
We have found 903 Cheshire Hotels
- The Red Lion Inn
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
- Howard Johnson by Wyndham Lenox
- Wagon Wheel Inn
- Shaker Mill Inn
- Chambery Inn
- Williamstown Motel
- Pilgrim Inn
- The Central Downtown Inn & Suites
- Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
- Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires
- Romantic Boutique Hotel / B&B - Deluxe Firespa Suite
- Northside Motel
- Romantic Boutique Hotel / Bed and Breakfast - Deluxe Schoolhouse Suite
- The Orchards Hotel
- Romantic Boutique Hotel / Bed and Breakfast - Standard King With Gas Fireplace
- Romantic Boutique Hotel / Bed and Breakfast - SchoolHouse Suite
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.