Find All Pittsfield Hotels
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Find All Pittsfield Hotels
We have found 1299 Pittsfield Hotels
- Berkshire Mountain Lodge
- Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
- Hotel On North
- Best Western Plus Berkshire Hills Inn & Suites
- Hilton Garden Inn Lenox Pittsfield
- FairBridge Inn Express
- Berkshire Inn
- Heart of the Berkshires
- The Central Downtown Inn & Suites
- Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
- Holiday Inn Express Pittsfield Berkshires, an IHG Hotel
- Mountain Lodge Apt!
- Spacious Historic Pittsfield Farmhouse
- Hotel Downstreet
- Life House Berkshires
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
- The Williams Inn
- The Red Lion Inn
- The Yankee, Trademark Collection by Wyndham
- The Black Swan Lee - Lenox, Ascend Hotel Collection
- The Little Lion
- Quality Inn
- Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
- The Constance, The Whitlock, & The Dewey By The Lenox Collection
- Fairfield Inn & Suites by Marriott Williamstown
- Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
- Courtyard by Marriott Lenox Berkshires
- Hampton Inn & Suites Berkshires-Lenox
- Quality Inn
- The Cornell Inn, Lenox
- The Porches Inn at Mass MoCA
- Comfort Inn & Suites East Greenbush - Albany
- The Villager Motel
- Chambery Inn
- Lakehouse Inn
- Club Wyndham Bentley Brook
- Monument Mountain Motel
- Berkshire Valley Inn
- Howard Johnson by Wyndham Williamstown
- Cozy Corner Motel
- Blue Vista Motor Lodge
- Howard Johnson by Wyndham Lenox
- Econo Lodge Lee - Great Barrington
- Willows Motel Williamstown
- East Rock Inn
- Pilgrim Inn
- Maple Terrace Motel
- The Brooks Motel
- Shaker Mill Inn
- Berkshire Travel Lodge
- Little Cat Lodge
- Wagon Wheel Inn
- The Egremont Village Inn
- The Trail in Adams - Berkshires’ Art Hotel
- 1896 House Country Inn & Motels
- Inn at Silver Maple Farm
- Pleasant Valley Motel West Stockbridge
- Tanglewood Suites
- 33 Main
- Devonfield Inn B&B
- Gregory House Country Inn
- Brook Farm Inn
- Travelodge by Wyndham Great Barrington Berkshires
- Apple Tree Inn
- Chatham Travel Lodge
- The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
- Charming Farmhouse - quiet, private & peaceful
- Four Season Motel
- Hudson valley and The Berkshires Cottage
- NEW RENO - Historic Loft w/views of the Berkshires
- Williamstown Motel
- 1789 Shaker Farmhouse in Berkshires/Hudson Valley
- Granville House
- Inn at Kenmore Hall
- Sunset Inn
- Gateways Inn & Restaurant
- SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires!
- Berkshire Rural Retreat
- NEW RENO - Chalet-style farm loft near Tanglewood
- In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
- All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
- Charming 5-bedroom farmhouse with AC, WiFi in delightful Ghent
- The Inn at Stockbridge
- Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!
- Harbour House Inn
- Whistler's Inn Bed & Breakfast
- Escape to this 120-acre farm in Upstate NY! Pet friendly.
- 1800s Carriage house in Berkshires / Hudson Valley
- Farm House Getaway on 200 acre horse farm!
- Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
- New 4500 sq ft modern 5 bed-5.5 bath on Housatonic River and walk to Stockbridge