Photo by Elizabeth Massa Peroulakis
Find All Chester Hotels
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Find All Chester Hotels
We have found 785 Chester Hotels
- Red Roof Inn PLUS+ West Springfield
- D. Hotel Suites & Spa
- Quality Inn West Springfield
- La Quinta Inn & Suites by Wyndham Springfield MA
- Life House Berkshires
- The Red Lion Inn
- The Yankee, Trademark Collection by Wyndham
- Tru by Hilton Chicopee Springfield
- The Black Swan Lee - Lenox, Ascend Hotel Collection
- The Ellery
- Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
- Homewood Suites by Hilton Hadley Amherst
- Homewood Suites by Hilton Holyoke-Springfield/North
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
- The Constance, The Whitlock, & The Dewey By The Lenox Collection
- Comfort Inn & Suites
- Courtyard by Marriott West Springfield
- Hampton Inn & Suites Berkshires-Lenox
- Hampton Inn West Springfield
- Quality Inn
- Hampton Inn Hadley-Amherst Area
- Candlewood Suites West Springfield, an IHG Hotel
- Fairfield Inn & Suites Springfield Northampton/Amherst
- Hotel Northampton
- Best Western Springfield West Inn
- Quality Inn & Suites Northampton - Amherst
- Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
- Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
- Riverdale Inn
- Hampton Inn Westfield
- Berkshire Mountain Lodge
- Courtyard by Marriott Lenox Berkshires
- Hampton Inn Chicopee/Springfield
- Fairfield Inn & Suites Springfield Holyoke
- Quality Inn Westfield - Springfield
- Residence Inn by Marriott West Springfield
- Monument Mountain Motel
- Best Western Plus Berkshire Hills Inn & Suites
- The Cornell Inn, Lenox
- Hotel On North
- Berkshire Inn
- Residence Inn Springfield Chicopee
- Hilton Garden Inn Lenox Pittsfield
- The Little Lion
- Howard Johnson by Wyndham Lenox
- Tru By Hilton Chicopee Springfield
- Old Mill Inn
- Travelodge by Wyndham Great Barrington Berkshires
- Wagon Wheel Inn
- Lakehouse Inn
- Econo Lodge Lee - Great Barrington
- Naomi's Inn Bed & Breakfast
- FairBridge Inn Express
- Pleasant Valley Motel West Stockbridge
- Chambery Inn
- Apple Tree Inn
- Pilgrim Inn
- Brook Farm Inn
- Devonfield Inn B&B
- 33 Main
- Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!
- The Central Downtown Inn & Suites
- Whistler's Inn Bed & Breakfast
- Charming Farmhouse - quiet, private & peaceful
- Sweet Dreams Retreat
- The Inn at Stockbridge
- Sunset Inn
- The Old Inn On The Green
- Gedney Farm
- The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!
- Gateways Inn & Restaurant
- Tanglewood Suites
- The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
- Charming, newly renovated, 3 bedroom farmhouse
- Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
- East Rock Inn
- Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires
- Becket Motel
- Harbour House Inn
- Romantic Boutique Hotel / B&B - Deluxe Firespa Suite
- Eastgate Inn B&B
- Elm Motel
- Romantic Boutique Hotel / Bed and Breakfast - Deluxe Schoolhouse Suite
- Seven Hills Inn
- Chambery Inn / 7,000 Sqft Luxury Historic Berkshire landmark on Main Street
- Historic 1817 Berkshire Farmhouse- Close to Everything!
- Kemble Inn
- Express Inn
- Farmhouse on Otis Pond
- Garden Gables Inn
- Eastover Estate & Eco-Village
- Romantic Boutique Hotel / Bed and Breakfast - Standard King With Gas Fireplace