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We have found 1009 Cheshire Hotels
- Harbour House Inn
- The Williams Inn
- Hotel Downstreet, Ascend Hotel Collection
- Berkshires Untold
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
- Holiday Inn & Suites Pittsfield-Berkshires by IHG
- FairBridge Inn Express
- Best Western Plus Berkshire Hills Inn & Suites
- Berkshire Mountain Lodge
- The Red Lion Inn
- The Yankee, Trademark Collection by Wyndham
- The Constance by the Lenox Collection
- Hampton Inn & Suites Berkshires-Lenox
- Howard Johnson by Wyndham Lenox
- Courtyard by Marriott Lenox Berkshires
- The Black Swan Lee - Lenox, Ascend Hotel Collection
- Quality Inn
- Hotel On North
- The Whitlock
- Berkshire Inn
- Fairfield Inn & Suites by Marriott Williamstown
- The Villager Motel
- Cozy Corner Motel
- The Cornell Inn, Lenox & The Berkshires
- Wagon Wheel Inn
- The Porches Inn at Mass MoCA
- Williamstown Motel
- Gregory House Country Inn
- The Dewey
- Econo Lodge Lee - Great Barrington
- Berkshire Travel Lodge
- Willows Motel Williamstown
- Hilton Garden Inn Lenox Pittsfield
- The Revival House
- Howard Johnson by Wyndham Williamstown
- The Springs Motel
- Blooming Inn
- Holiday Inn Express & Suites Pittsfield - Berkshires
- Element Lenox Berkshires
- Pleasant Valley Motel West Stockbridge
- Chambery Inn
- Berkshire Valley Inn
- Pilgrim Inn
- 1896 House Country Inn & Motels
- Blue Vista Motor Lodge
- Tanglewood Suites
- Club Wyndham Bentley Brook
- Inn at Silver Maple Farm
- The Central Downtown Inn & Suites
- Lakehouse Inn
- Brook Farm Inn
- Whistler's Inn Bed & Breakfast
- Maple Terrace Motel
- Sunset Inn
- Shaker Mill Inn
- Apple Tree Inn
- Becket Motel
- Berkshire Village Carriage House - Super Private!!
- Devonfield Inn B&B
- NEW RENO Historic Creamery in Berkshires w/hot tub
- The Trail in Adams - Berkshires’ Art Hotel
- Starlight Inn
- Gateways Inn & Restaurant
- The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
- Charming Farmhouse - quiet, private & peaceful
- 1789 Shaker Farmhouse in Berkshires/Hudson Valley
- NEW RENO - Historic Loft w/views of the Berkshires
- 1800s Carriage house in Berkshires / Hudson Valley
- 33 Main
- In town, newly remodeled studio with private balcony
- NEW RENO - Chalet-style farm loft near Tanglewood
- All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
- The Orchards Hotel
- Cranwell Spa and Golf Resort
- Seven Hills Inn
- 26 Church Street
- Inn at Kenmore Hall
- The Inn at Stockbridge
- Holiday Inn Club Vacations Oak 'n Spruce Resort
- Eastgate Inn B&B
- Live history in the restored Parsonage and have fun on the river and mountains.
- Berkshire Mountain House
- Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!
- Eastover Estate & Eco-Village
- In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
- Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
- 67 Church Street
- Ladd Brook Inn
- Historic Stone Church in The Berkshires
- Modern Country Farmhouse, Walking Distance to Lake
- Experience Timeless Elegance in The Edith Wharton Room!