Find All Windsor Hotels
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Find All Windsor Hotels
We have found 929 Windsor Hotels
- Eastover Estate & Eco-Village
- Doctor Sax House
- Becket Motel
- Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
- Stay Berkshires
- Holiday Inn Express Pittsfield Berkshires, an IHG Hotel
- Spacious Farmhouse with Stunning Views
- Tourists
- The Springs Motel
- Hot SKI-in SKI-out Rentals Bentley Brook Resort!
- Cozy Retreat in the Berkshires - Apple Room in Orchard Guest House
- Charming Farmhouse; 2 Bed / 2 Bath, only 1.5 miles to Jiminy Peak. Pet Friendly.
- Cozy Retreat in the Berkshires - Cherry Room in Orchard Guest House
- 18th century 3-bedroom renovated farmhouse in peaceful Whately with WiFi, AC
- Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss
- Garden Gables Inn
- Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - B
- Restored historic farmhouse on 25 private acres
- Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A
- Ski Jiminy Peak - Lg 1 Bd - Vacation Village in the Berkshires
- Berkshire Mountain House
- Bentley Brook, Charming 2-bedroom with WiFi, at Jiminy Peak Ski Resort
- Hampton Terrace Inn
- The Orchards Hotel
- The Red Door B&B
- Farmhouse on Otis Pond
- Guest House Sanctuary by Evergreen Home
- The Retreat at Norwich Lake
- Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out
- Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl
- Vacation Village in the Berkshires 5 Star Resort - Suite A
- Vacation Village In The Berkshires 5 Star Resort - Suite B
- Kemble Inn
- Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury
- Jacob's Tanglewood Ranch
- Historic 1817 Berkshire Farmhouse- Close to Everything!
- Northside Motel
- Chesapeake Inn of Lenox
- Bentley Brook at Jiminy Peak ^ Studio
- Holiday Inn Club Vacations Oak 'n Spruce Resort
- Cozy Farmhouse Retreat for One - Lagniappe Room
- Orchard Guest House: Cozy Berkshire Retreat in the Woods
- The Kemble Berkshires
- Cozy Farmhouse Retreat - Monk’s Room
- Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort
- Secluded 19th century Farmhouse with mountain views
- Your Winter Escape: Wyndham Bentley Brook Ski-In, Ski-Out Bliss at Jiminy Peak!"
- Ladd Brook Inn
- Lenox Inn
- 67 Church Street
- Green Valley Motel
- Terrific 2-bedroom resort in Lee with WiFi, fitness room, AC
- 26 Church Street
- Cozy Retreat in the Berkshires - Harvest Room in Orchard Guest House
- The Weathervane Motel
- Chestnut Lodge
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires
- Cozy and large 2 Bedroom 2 Full Bath ski in, ski out condo Unit with balcony.
- Charming 2-bedroom resort in marvelous Hancock with AC, fitness room, WiFi
- Mountain Lodge Apt!
- Cozy 1-bedroom at a New England style resort in the Berkshire mountains
- ONTARA....
- Canyon Ranch Lenox
- Renovated Berkshires Farmhouse - minutes from hiking, swimming, and Tanglewood
- UU Rowe Camp and Conference Center