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 800 Chester Hotels
- D. Hotel Suites & Spa
- La Quinta Inn & Suites by Wyndham Springfield MA
- Red Roof Inn PLUS+ West Springfield
- Quality Inn West Springfield
- Life House Berkshires
- The Yankee, Trademark Collection by Wyndham
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
- Candlewood Suites West Springfield by IHG
- Tru by Hilton Chicopee Springfield
- The Ellery
- The Black Swan Lee - Lenox, Ascend Hotel Collection
- The Red Lion Inn
- Fairfield Inn & Suites Springfield Northampton/Amherst
- Homewood Suites by Hilton Holyoke-Springfield/North
- Hampton Inn West Springfield
- Homewood Suites by Hilton Hadley Amherst
- The Constance, The Whitlock, & The Dewey By The Lenox Collection
- Quality Inn & Suites Northampton - Amherst
- Hotel On North
- Berkshire Mountain Lodge
- Courtyard by Marriott West Springfield
- Comfort Inn & Suites
- Fairfield Inn & Suites Springfield Holyoke
- Best Western Springfield West Inn
- Holiday Inn & Suites Pittsfield-Berkshires by IHG
- Regency Inn & Suites
- The Cornell Inn, Lenox & The Berkshires
- Hampton Inn Hadley-Amherst Area
- Howard Johnson by Wyndham Lenox
- Courtyard by Marriott Lenox Berkshires
- Hotel Northampton
- Quality Inn Westfield - Springfield
- The Little Lion
- Quality Inn
- Residence Inn Springfield Chicopee
- The Central Downtown Inn & Suites
- Best Western Plus Berkshire Hills Inn & Suites
- Hampton Inn & Suites Berkshires-Lenox
- Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
- Holiday Inn Express Hotel & Suites Great Barrington by IHG
- Hatfield Inn
- Hampton Inn Westfield
- TownePlace Suites by Marriott Hadley Amherst
- Residence Inn by Marriott West Springfield
- Tru By Hilton Chicopee Springfield
- Hampton Inn Chicopee/Springfield
- Riverdale Inn
- Old Mill Inn
- Hilton Garden Inn Lenox Pittsfield
- Monument Mountain Motel
- Berkshire Inn
- Chambery Inn
- FairBridge Inn Express
- Pleasant Valley Motel West Stockbridge
- Econo Lodge Lee - Great Barrington
- Lakehouse Inn
- Wagon Wheel Inn
- Pilgrim Inn
- Charming Farmhouse - quiet, private & peaceful
- Naomi's Inn Bed & Breakfast
- Devonfield Inn B&B
- Brook Farm Inn
- Travelodge by Wyndham Great Barrington Berkshires
- East Rock Inn
- Sunset Inn
- A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
- Heart of the Berkshires
- Whistler's Inn Bed & Breakfast
- Daniel Stebbins House
- The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
- 33 Main
- The Old Inn On The Green
- The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!
- The Inn at Stockbridge
- Gedney Farm
- Gateways Inn & Restaurant
- Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!
- Apple Tree Inn
- Tanglewood Suites
- Experience a charming 3 bedroom farm stay close to winter activity.
- New 4500 sq ft modern 5 bed-5.5 bath on Housatonic River and walk to Stockbridge
- Historic Stone Church in The Berkshires
- Spacious Farmhouse with Stunning Views
- Harbour House Inn
- Holiday Inn Express Pittsfield Berkshires by IHG
- Eastgate Inn B&B
- Knights Inn Hadley
- Seven Hills Inn
- Becket Motel
- Cranwell Spa and Golf Resort
- Eastover Estate & Eco-Village
- Express Inn
- 18th century Berkshires farmhouse on 12 acres, impeccably updated.
- Elm Motel