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Featured Pittsfield Family Hotels

Hotel On North
Hotel On North
3.5 out of 5
297 North Street, Pittsfield, MA
Fully refundableReserve now, pay when you stay
Stay at this 3.5-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
Hotel On North
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
2.5 out of 5
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 ...
Best Western Plus Berkshire Hills Inn & Suites
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3 out of 5
One West Street, Pittsfield, MA
Fully refundable
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Berkshire Inn
Berkshire Inn
2 out of 5
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. ...
Berkshire Inn
FairBridge Inn Express
FairBridge Inn Express
2.5 out of 5
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 ...
FairBridge Inn Express
Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox Pittsfield
3 out of 5
1032 South Street, Pittsfield, MA
Fully refundableReserve now, pay when you stay
Stay at this 3-star hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
Hilton Garden Inn Lenox Pittsfield
The Central Downtown Inn & Suites
The Central Downtown Inn & Suites
4 out of 5
20 W Housatonic St., Pittsfield, MA
Stay at this 4-star guesthouse in Pittsfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Colonial Theater and Berkshire Museum ...
The Central Downtown Inn & Suites
See all 1,313 properties in Pittsfield
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
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3 out of 5
One West Street, Pittsfield, MA
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (758 reviews)
"Easy check in, nice staff. Rug in the room was kind of musty. They were accommodating to me requesting to have a slightly later check out. Would return if in the area."

Reviewed on Mar 18, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Berkshire Inn
Berkshire Inn
2 out of 5
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! (762 reviews)
"The room was very clean"

Reviewed on Feb 8, 2025

Berkshire Inn
Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox Pittsfield
3 out of 5
1032 South Street, Pittsfield, MA
Stay at this 3-star hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
9.2/10 Wonderful! (628 reviews)
"Very clean and comfortable with great restaurant and bar downstairs"

Reviewed on Jan 29, 2025

Hilton Garden Inn Lenox Pittsfield
See all 1,313 properties in Pittsfield
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
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3 out of 5
One West Street, Pittsfield, MA
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox Pittsfield
3 out of 5
1032 South Street, Pittsfield, MA
Stay at this 3-star hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
Hilton Garden Inn Lenox Pittsfield
Hotel On North
Hotel On North
3.5 out of 5
297 North Street, Pittsfield, MA
Stay at this 3.5-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
Hotel On North
See all 1,313 properties in Pittsfield
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.