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 797 Chester Hotels
- D. Hotel Suites & Spa
- Red Roof Inn PLUS+ West Springfield
- Tru by Hilton Chicopee Springfield
- Life House Berkshires
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
- The Yankee, Trademark Collection by Wyndham
- La Quinta Inn & Suites by Wyndham Springfield MA
- The Red Lion Inn
- Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
- The Black Swan Lee - Lenox, Ascend Hotel Collection
- The Ellery
- Hotel On North
- Homewood Suites by Hilton Holyoke-Springfield/North
- Quality Inn West Springfield
- Hampton Inn West Springfield
- Fairfield Inn & Suites Springfield Northampton/Amherst
- Hotel Northampton
- Homewood Suites by Hilton Hadley Amherst
- Regency Inn & Suites
- Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
- Comfort Inn & Suites
- Hampton Inn & Suites Berkshires-Lenox
- Quality Inn
- Residence Inn by Marriott West Springfield
- Hampton Inn Chicopee/Springfield
- The Constance, The Whitlock, & The Dewey By The Lenox Collection
- Berkshire Mountain Lodge
- The Little Lion
- Best Western Plus Berkshire Hills Inn & Suites
- Courtyard by Marriott Lenox Berkshires
- Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
- Hampton Inn Hadley-Amherst Area
- The Cornell Inn, Lenox
- Quality Inn & Suites Northampton - Amherst
- FairBridge Inn Express
- Courtyard by Marriott West Springfield
- Candlewood Suites West Springfield, an IHG Hotel
- Monument Mountain Motel
- Best Western Springfield West Inn
- Hampton Inn Westfield
- Fairfield Inn & Suites Springfield Holyoke
- Hilton Garden Inn Lenox Pittsfield
- Lakehouse Inn
- Howard Johnson by Wyndham Lenox
- Tru By Hilton Chicopee Springfield
- Old Mill Inn
- Travelodge by Wyndham Great Barrington Berkshires
- Berkshire Inn
- Quality Inn Westfield - Springfield
- Residence Inn Springfield Chicopee
- Chambery Inn
- Naomi's Inn Bed & Breakfast
- Wagon Wheel Inn
- Pilgrim Inn
- Econo Lodge Lee - Great Barrington
- Riverdale Inn
- Brook Farm Inn
- Tanglewood Suites
- 33 Main
- Devonfield Inn B&B
- Pleasant Valley Motel West Stockbridge
- East Rock Inn
- The Central Downtown Inn & Suites
- Heart of the Berkshires
- Apple Tree Inn
- The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!
- The Inn at Stockbridge
- The Old Inn On The Green
- Charming Farmhouse - quiet, private & peaceful
- The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
- Gateways Inn & Restaurant
- Gedney Farm
- Experience a charming 3 bedroom farm stay close to winter activity.
- Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
- Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires
- 18th century Berkshires farmhouse on 12 acres, impeccably updated.
- Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!
- Sunset Inn
- Country living with hill town views above the clouds!
- New 4500 sq ft modern 5 bed-5.5 bath on Housatonic River and walk to Stockbridge
- Harbour House Inn
- Seven Hills Inn
- Becket Motel
- Elm Motel
- Lantern House Motel
- Cranwell Spa and Golf Resort
- Whistler's Inn Bed & Breakfast
- Express Inn
- Romantic Boutique Hotel / Bed and Breakfast - Deluxe Schoolhouse Suite
- Historic 1817 Berkshire Farmhouse- Close to Everything!
- Chambery Inn / 7,000 Sqft Luxury Historic Berkshire landmark on Main Street
- Eastover Estate & Eco-Village