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Find All Cheshire Hotels
We have found 987 Cheshire Hotels
- UU Rowe Camp and Conference Center
- New 4500 sq ft modern 5 bed-5.5 bath on Housatonic River and walk to Stockbridge
- Cranwell Spa and Golf Resort
- Bentley Brook the perfect home base for exploring nearby Berkshire County
- Stay Berkshires
- Hampton Terrace Inn
- Kemble Inn
- Restored historic farmhouse on 25 private acres
- 67 Church Street
- Modern Country Farmhouse, Walking Distance to Lake
- Unique people and pet welcoming haven
- Green Valley Motel
- 26 Church Street
- Bentley Brook the perfect home base for exploring nearby Berkshire County
- Cozy Carriage House room with a double bed and private balcony
- Heart of the Berkshires
- Summer Ready! Play Area, Crib, 11 Acre Farmhouse
- Lg 1 Bd - Vacation Village in the Berkshires
- COZY CABIN IN BERKSHIRES RESORT - LABOR DAY SALE
- The Red Door B&B
- Jacob's Tanglewood Ranch
- Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out
- "Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
- Tourists
- Charming Farmhouse; 2 Bed / 2 Bath, only 1.5 miles to Jiminy Peak. Pet Friendly.
- The Whitlock
- Elegant Carriage House room with a queen bed and private patio.
- Northside Motel
- Chesapeake Inn of Lenox
- Cliffwood Cottage by Evergreen Home
- Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
- Bentley Brook 1-bedroom Mountainside ski resort in charming Hancock sleeps 8
- Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A
- Vacation Village In The Berkshires 5 Star Resort - Suite B
- Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss
- Guest House Sanctuary by Evergreen Home
- Secluded 19th century Farmhouse with mountain views
- Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
- Jiminy Premier Ski-In/Ski-Out Resort Bentley B
- Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl
- Historic 1817 Berkshire Farmhouse- Close to Everything!
- Bentley Brook at Jiminy Peak ^ Studio
- Pres Week- Bentley Brook Resort - Your Peak Winter Escape
- Bentley Brook, Charming 2-bedroom with WiFi, at Jiminy Peak Ski Resort
- Hot SKI-in SKI-out Rentals Bentley Brook Resort!
- Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
- Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
- Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort
- Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury
- Ladd Brook Inn
- Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
- The Kemble Berkshires
- Terrific 2-bedroom resort in Lee with WiFi, fitness room, AC
- ONTARA....
- Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - B
- Berkshire Mountain Lodge
- The Weathervane Motel
- Cozy and large 2 Bedroom 2 Full Bath ski in, ski out condo Unit with balcony.
- Your Winter Escape: Wyndham Bentley Brook Ski-In, Ski-Out Bliss at Jiminy Peak!"
- Charming 2-bedroom resort in marvelous Hancock with AC, fitness room, WiFi
- Mountain Lodge Apt!
- Canyon Ranch Lenox
- Renovated Berkshires Farmhouse - minutes from hiking, swimming, and Tanglewood
- Chestnut Lodge
- Element Lenox Berkshires
- NEW RENO Historic Creamery in Berkshires w/hot tub
- Oak 'n Spruce Resort 2 Bedrooms in The Berkshires an IHG and Holiday Inn Club