See all 1270 hotels in Sheffield
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
- Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
- Prospect Berkshires
- Element Lenox Berkshires
- The Whitlock
- The Dewey
- Troutbeck
- Locust Tree Bed and Breakfast LLC
- The Millerton Inn
- Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
- Charming 5-bedroom farmhouse with AC, WiFi in delightful Ghent
- Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
- Hudson Valley Dream Farmhouse: Bike Trails, Wineries, Five Acres
- A Writer's Retreat at The Barn
- Copper Kettle Farm - newly renovated farmhouse with spectacular views
- Experience Timeless Elegance in The Edith Wharton Room!