Pittsfield Vacations

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Find the Best Pittsfield Vacation Packages

Pittsfield Hotel Deals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is ₩215,395 per night from Jul 27 to Jul 28
₩215,395
₩274,883 total
Jul 27 - Jul 28
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"The room in lobby were great. The big front porch was actually a nice thing to have, because the fire pit was closed (and the guy worked the front desk at night said he didn’t have a key to start it.) The bar was closed. The boutique was closed and there really wasn’t anywhere else you could go. ..."

Reviewed on Jun 26, 2026

Berkshire Mountain Lodge
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
Fully refundable
The price is ₩262,446 per night from Jul 6 to Jul 7
₩262,446
₩293,157 total
Jul 6 - Jul 7
includes taxes & fees
9.4/10 Exceptional! (116 reviews)
"Best hotel breakfast I have had in a long time. The breakfast attendant kept items well stocked. She made sure that vacated tables were cleaned and ready for the next guests to enjoy their meal. The room was kept very clean. I really enjoyed the fresh pancakes that were made to order by a pancake ..."

Reviewed on Jun 26, 2026

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is ₩382,158 per night from Jul 7 to Jul 8
₩382,158
₩426,866 total
Jul 7 - Jul 8
includes taxes & fees
9.6/10 Exceptional! (869 reviews)
"Always a great experience at Hotel on North! Great, comfortable room with amazing bathroom. Helpful and friendly staff. Safe parking in the rear secured lot."

Reviewed on Jun 24, 2026

Hotel On North
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.

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