See all 1334 hotels in Pittsfield
- Harbour House Inn
- Charming 5-bedroom farmhouse with AC, WiFi in delightful Ghent
- Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
- Farmhouse Retreat, Outdoor Dining/Fire-Pit, Fast Wifi, Golf & 3-Acre Privacy
- Bentley Brook the perfect home base for exploring nearby Berkshire County
- A Writer's Retreat at The Barn
- Experience Timeless Elegance in The Edith Wharton Room!
- Monk's Bunk, Old Chatham
- Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
- Bentley Brook the perfect home base for exploring nearby Berkshire County
- Historic Susan B. Anthony Room - Cozy & Charming Stay
- Bentley Brook the perfect home base for exploring nearby Berkshire County
- Cozy Carriage House room with a double bed and private balcony
- Farm House Getaway on beautiful horse farm!
- "Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
- Charming 6 Bdrm Countryside Stay
- 1 Bd - Vacation Village in the Berkshires
- Come to our lake house, pick apples, kayak & enjoy the fall foliage.
- Elegant Carriage House room with a queen bed and private patio.
- Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
- Elegant suite with a king bed, fireplace, and kitchenette.
- Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
- 18th century Berkshires farmhouse on 12 acres, impeccably updated.
- Tastefully Restored Berkshire Farmhouse Available October 15th - 31st 2024
- Cliffwood Cottage by Evergreen Home
- Rustic 4-bedroom farmhouse in bucolic Hinsdale, MA
- Club Wyndham Bentley Brook
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