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Featured Pittsfield Family Hotels
Hotel On North
297 North Street Pittsfield MA
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St Pittsfield MA
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Berkshire Inn
150 W Housatonic St Pittsfield MA
Fully refundableReserve now, pay when you stay
Stay at this motel in Pittsfield. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
FairBridge Inn Express
16 Cheshire Road Pittsfield MA
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking ...
Hilton Garden Inn Lenox Pittsfield
1032 South Street Pittsfield MA
Fully refundableReserve now, pay when you stay
Stay at this hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
The Central Downtown Inn & Suites
20 W Housatonic St. Pittsfield MA
Stay at this guesthouse in Pittsfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Colonial Theater and Berkshire Museum are located ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Hotels with Pools in Pittsfield
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (975 reviews)
The room was clean, and staff who checked us in was both courteous and informative.
Reviewed on Nov 28, 2025
Berkshire Inn
150 W Housatonic St Pittsfield MA
Stay at this motel in Pittsfield. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.6/10 Good! (838 reviews)
The room is good, it’s clean. However need more lighting in room, except for bathroom are so super clean and beautiful setting!! Bed is very comfortable to sleep, easily to sleep quickly. I would come back again when I use this place.
Reviewed on Dec 3, 2025
Hilton Garden Inn Lenox Pittsfield
1032 South Street Pittsfield MA
Stay at this hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
9.2/10 Wonderful! (656 reviews)
Clean and convenient to Mt. Greylock. Kind staff.
Reviewed on Nov 14, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Hotels With Connecting Rooms in Pittsfield
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Hilton Garden Inn Lenox Pittsfield
1032 South Street Pittsfield MA
Stay at this hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
Hotel On North
297 North Street Pittsfield MA
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Hotels by Star Rating
More Hotel Options
- Historic Hotels in Pittsfield
- Hotels with Free Parking in Pittsfield
- Luxury Hotels in Pittsfield
- Pet-friendly Hotels in Pittsfield
- Hotels with a Pool in Pittsfield
- Apartment Hotel in Pittsfield
- Romantic Hotels in Pittsfield
- Winery Hotels in Pittsfield
- Hotels with Hot Tubs in Pittsfield
- Resorts & Hotels with Spas in Pittsfield
Top Points of Interests in Pittsfield
- Hotels near Bousquet Ski Area
- Hotels near Colonial Theater
- Hotels near Hancock Shaker Village
- Hotels near Berkshire Museum
- Hotels near Barrington Stage Company
- Hotels near Guido's Marketplace
- Hotels near Berkshire Athenaeum
- Hotels near Canoe Meadows Wildlife Sanctuary
- Hotels near Crane Museum of Papermaking
- Hotels near Herman Melville's Arrowhead
- Hotels near Jiminy Peak Mountain Resort
- Hotels near Tanglewood Music Center
- Hotels near Ski Butternut
- Hotels near Catamount Ski Area
- Hotels near Massachusetts Museum of Contemporary Art
- Hotels near Green Mountain National Forest
- Hotels near National Shrine of the Divine Mercy
- Hotels near Williams College
- Hotels near Berkshire East Ski Resort
- Hotels near The Clark Art Institute
Cities near Pittsfield
- Upstate New York Hotels (128.56 mi)
- Hudson Hotels (30.55 mi)
- The Berkshires Hotels (20.16 mi)
- Williamstown Hotels (18.38 mi)
- Lenox Hotels (6.51 mi)
- Hudson Valley Hotels (65.64 mi)
- Great Barrington Hotels (18.29 mi)
- Stockbridge Hotels (11.61 mi)
- Troy Hotels (29.48 mi)
- Lee Hotels (9.96 mi)
- North Adams Hotels (18.77 mi)
- Hudson River Valley Hotels (89.68 mi)
- Hancock Hotels (7 mi)
- East Greenbush Hotels (24.83 mi)
- Appalachian Mountains Hotels (258.56 mi)
- Rensselaer Hotels (28.26 mi)
- Housatonic Hotels (14.12 mi)
- Western Massachusetts Hotels (20.97 mi)
- South Lee Hotels (11.84 mi)
- Hillsdale Hotels (23.18 mi)