Photo by Ed Gaffny
Find All Cheshire Hotels
Find All Cheshire Hotels
We have found 953 Cheshire Hotels
- Harbour House Inn
- Life House Berkshires
- The Yankee, Trademark Collection by Wyndham
- The Williams Inn
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
- Holiday Inn & Suites Pittsfield-Berkshires by IHG
- The Red Lion Inn
- Hotel Downstreet, Ascend Hotel Collection
- The Black Swan Lee - Lenox, Ascend Hotel Collection
- Berkshire Mountain Lodge
- Hotel On North
- The Constance, The Whitlock, & The Dewey By The Lenox Collection
- Courtyard by Marriott Lenox Berkshires
- Fairfield Inn & Suites by Marriott Williamstown
- Quality Inn
- The Porches Inn at Mass MoCA
- Hampton Inn & Suites Berkshires-Lenox
- The Cornell Inn, Lenox & The Berkshires
- Best Western Plus Berkshire Hills Inn & Suites
- FairBridge Inn Express
- Club Wyndham Bentley Brook
- Howard Johnson by Wyndham Williamstown
- The Villager Motel
- Hilton Garden Inn Lenox Pittsfield
- Howard Johnson by Wyndham Lenox
- Berkshire Inn
- Maple Terrace Motel
- Lakehouse Inn
- Cozy Corner Motel
- Willows Motel Williamstown
- Blooming Inn
- Chambery Inn
- Blue Vista Motor Lodge
- Pleasant Valley Motel West Stockbridge
- Pilgrim Inn
- Gregory House Country Inn
- Berkshire Valley Inn
- Wagon Wheel Inn
- Berkshire Travel Lodge
- Econo Lodge Lee - Great Barrington
- The Trail in Adams - Berkshires’ Art Hotel
- The Central Downtown Inn & Suites
- Williamstown Motel
- Starlight Inn
- Brook Farm Inn
- Heart of the Berkshires
- Sunset Inn
- Inn at Silver Maple Farm
- Shaker Mill Inn
- Charming Farmhouse - quiet, private & peaceful
- Devonfield Inn B&B
- 1896 House Country Inn & Motels
- 33 Main
- In town, newly remodeled studio with private balcony
- Apple Tree Inn
- Tanglewood Suites
- Whistler's Inn Bed & Breakfast
- The Springs Motel
- 1789 Shaker Farmhouse in Berkshires/Hudson Valley
- The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
- Gateways Inn & Restaurant
- In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
- NEW RENO - Historic Loft w/views of the Berkshires
- SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires!
- Inn at Kenmore Hall
- Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!
- The Inn at Stockbridge
- NEW RENO - Chalet-style farm loft near Tanglewood
- All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
- Spacious Farmhouse with Stunning Views
- New 4500 sq ft modern 5 bed-5.5 bath on Housatonic River and walk to Stockbridge
- Seven Hills Inn
- Holiday Inn Express Pittsfield Berkshires by IHG
- Berkshire Rural Retreat
- Historic Stone Church in The Berkshires
- 1800s Carriage house in Berkshires / Hudson Valley
- Rural charm a mile from Berkshire East Ski Resort and 29 miles from Mt. Snow.
- Modern Country Farmhouse, Walking Distance to Lake
- Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
- Ski Season! Play Area, Crib, 11 Acre Farmhouse
- Chambery Inn / 7,000 Sqft Luxury Historic Berkshire landmark on Main Street
- Stay Berkshires
- Eastgate Inn B&B
- Pres Week- Bentley Brook Resort - Your Peak Winter Escape
- Eastover Estate & Eco-Village
- Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
- Cranwell Spa and Golf Resort
- Jiminy Premier Ski-In/Ski-Out Resort Bentley B
- Ski Jiminy Peak - Lg 1 Bd - Vacation Village in the Berkshires