Pittsfield Vacations
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Find the Best Pittsfield Vacation Packages
Pittsfield Hotel Deals
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is NT$2,768 per night from May 3 to May 4
NT$2,768
NT$3,806 total
May 3 - May 4
includes taxes & fees
9/10 Wonderful! (894 reviews)
Clean, quiet, spacious, comfortable, and lovely furnishings! It was a very relaxing overnight.
Reviewed on 2026/3/31
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Fully refundable
The price is NT$3,743 per night from Apr 17 to Apr 18
NT$3,743
NT$4,180 total
Apr 17 - Apr 18
includes taxes & fees
8/10 Very Good! (1,000 reviews)
OK, the hotel needs updating, but the staff was so friendly and helpful it didn't even matter. We parked our car, walked everywhere, 2 min to the Colonial theater! Insider tip, if you buy a breakfast tix from the front desk it's less $ than paying at the restaurant.
Reviewed on 2026/3/29
Hotel On North
297 North Street Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is NT$4,762 per night from Apr 8 to Apr 9
NT$4,762
NT$5,319 total
Apr 8 - Apr 9
includes taxes & fees
9.6/10 Exceptional! (842 reviews)
What a lovely room and building. Really enjoyed this hotel. However, the neighborhood outside the hotel was very sketchy and clearly there is an issue with drug addiction in the area. I ate at the restaurant within the hotel and went to and from my car in the gated lot. I enjoyed many other towns ...
Reviewed on 2026/4/3
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.
Discover the most popular places to visit in Pittsfield
Bousquet Ski Area
4/5(9 reviews)
Hit the slopes at Bousquet Ski Area during your trip to Pittsfield. Wander the lakeside in this family-friendly area.
Colonial Theater
3.5/5(3 reviews)
You can make plans for a show at Colonial Theater during your trip to Pittsfield. Wander the lakeside in this family-friendly area.
Barrington Stage Company
You can make plans for a show at Barrington Stage Company on your trip to Pittsfield. Wander the lakeside in this quaint area.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
