All hotels in Windsor, 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 Windsor, Massachusetts
We have found 921 Windsor Hotels
- Life House Berkshires
- The Williams Inn
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
- Hotel Downstreet
- The Yankee, Trademark Collection by Wyndham
- Berkshire Mountain Lodge
- The Red Lion Inn
- The Black Swan Lee - Lenox, Ascend Hotel Collection
- Hotel On North
- Fairfield Inn & Suites by Marriott Williamstown
- The Constance, The Whitlock, & The Dewey By The Lenox Collection
- Best Western Plus Berkshire Hills Inn & Suites
- Hampton Inn & Suites Berkshires-Lenox
- FairBridge Inn Express
- Quality Inn
- The Porches Inn at Mass MoCA
- The Cornell Inn, Lenox
- The Villager Motel
- Club Wyndham Bentley Brook
- Lakehouse Inn
- Berkshire Valley Inn
- Chambery Inn
- Berkshire Inn
- Cozy Corner Motel
- Willows Motel Williamstown
- Blooming Inn
- Maple Terrace Motel
- Wagon Wheel Inn
- Howard Johnson by Wyndham Williamstown
- The Trail in Adams - Berkshires’ Art Hotel
- Pleasant Valley Motel West Stockbridge
- 1896 House Country Inn & Motels
- 33 Main
- Berkshire Travel Lodge
- Heart of the Berkshires
- Inn at Silver Maple Farm
- Devonfield Inn B&B
- The Central Downtown Inn & Suites
- Apple Tree Inn
- Tanglewood Suites
- Williamstown Motel
- NEW RENO - Historic Loft w/views of the Berkshires
- In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
- Sunset Inn
- All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
- Inn at Kenmore Hall
- 1789 Shaker Farmhouse in Berkshires/Hudson Valley
- NEW RENO - Chalet-style farm loft near Tanglewood
- The Inn at Stockbridge
- 1800s Carriage house in Berkshires / Hudson Valley
- Seven Hills Inn
- Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
- Harbour House Inn
- Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
- Whistler's Inn Bed & Breakfast
- Stay Berkshires
- Eastover Estate & Eco-Village
- Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
- Chambery Inn / 7,000 Sqft Luxury Historic Berkshire landmark on Main Street
- Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
Let Expedia take you to the best Hotels in Windsor. 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.