See all 1344 hotels in Pittsfield
- Hotel On North
- Best Western Plus Berkshire Hills Inn & Suites
- Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
- Berkshire Inn
- FairBridge Inn Express
- Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
- Heart of the Berkshires
- Mountain Lodge Apt!
- Berkshire Mountain Lodge
- Hotel Downstreet, an Ascend Collection Hotel
- Berkshires Untold
- The Williams Inn
- The Yankee, Trademark Collection by Wyndham
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
- The Black Swan Lee - Lenox, an Ascend Collection Hotel
- The Red Lion Inn
- Quality Inn Great Barrington
- Comfort Inn & Suites East Greenbush - Albany
- The Porches Inn at Mass MoCA
- Courtyard by Marriott Lenox Berkshires
- Holiday Inn Express Hotel & Suites Great Barrington by IHG
- The Cornell Inn, Lenox & The Berkshires
- Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
- Hampton Inn & Suites Berkshires-Lenox
- Prospect Berkshires
- The Little Lion
- Element Lenox Berkshires
- The Whitlock
- Quality Inn Lee - Lenox South
- Monument Mountain Motel
- Howard Johnson by Wyndham Lenox
- Willows Motel Williamstown
- Pilgrim Inn
- Chambery Inn
- Blue Vista Motor Lodge
- Cozy Corner Motel
- Pleasant Valley Motel West Stockbridge
- Travelodge by Wyndham Great Barrington Berkshires
- The Berkshire Mountain Inn
- Devonfield Inn B&B
- Maple Terrace Motel
- The Brooks Motel
- The Springs Motel
- Rodeway Inn
- Lakehouse Inn
- Gregory House Country Inn
- Shaker Mill Inn
- Econo Lodge Lee - Great Barrington
- Berkshire Village Carriage House - Super Private!!
- East Rock Inn
- Berkshire Travel Lodge
- Berkshire Valley Inn
- Whistler's Inn Bed & Breakfast
- The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
- The Inn at Stockbridge
- Inn at Silver Maple Farm
- The Trail in Adams - Berkshires’ Art Hotel
- The Revival House
- Chatham Travel Lodge
- Granville House
- Cranwell Spa and Golf Resort
- Farmhouse Retreat, Outdoor Dining/Fire-Pit, Fast Wifi, Golf & 3-Acre Privacy
- 1896 House Country Inn & Motels
- NEW RENO - Historic Loft w/views of the Berkshires
- 1800s Carriage house in Berkshires / Hudson Valley
- NEW RENO Historic Creamery in Berkshires w/hot tub
- Gateways Inn & Restaurant
- Club Wyndham Bentley Brook
- In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
- Four Season Motel
- Hideaway Inn Lenox
- 33 Main
- Hampton Terrace Inn
- Monk's Bunk, Old Chatham
- Hudson valley and The Berkshires Cottage
- 1789 Shaker Farmhouse in Berkshires/Hudson Valley
- Charming Farmhouse - quiet, private & peaceful
- Charming 5-bedroom farmhouse with AC, WiFi in delightful Ghent
- Inn at Kenmore Hall
- Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
- Harbour House Inn
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