Find Historic Hotels in Pittsfield, MA

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Pick from 8 Pittsfield Historic Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

Hotel On North
3.5 star property
9.6 out of 10, Exceptional, (645)
"Fun decor and comfy beds. Lovely bathroom. Highly recommend."
The price is NT$4,626
NT$5,168 total
includes taxes & fees
Nov 6 - Nov 7
Hotel On North
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3.0 star property
7.8 out of 10, Good, (670)
"My stay at the Holiday Inn was very pleasant!"
The price is NT$3,001
NT$3,353 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Hilton Garden Inn Lenox Pittsfield
3.0 star property
9.2 out of 10, Wonderful, (615)
"Nice"
The price is NT$4,559
NT$5,092 total
includes taxes & fees
Dec 1 - Dec 2
Hilton Garden Inn Lenox Pittsfield
Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
8.4 out of 10, Very Good, (1000)
"Staff was extremely friendly and helpful!! Anything we needed they had options for us. AAA !"
The price is NT$3,244
NT$3,624 total
includes taxes & fees
Nov 26 - Nov 27
Best Western Plus Berkshire Hills Inn & Suites
Berkshire Inn
2.0 star property
7.6 out of 10, Good, (741)
"The staff was wonderful. Unfortunately I couldn’t get the internet to work. No worries I just tethered my phone "
The price is NT$2,579
NT$2,881 total
includes taxes & fees
Nov 7 - Nov 8
Berkshire Inn
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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Frequently asked questions

What should a history enthusiast expect from a trip to Pittsfield?
The historical places in Pittsfield are probably at the top of your sightseeing list. During your visit, you can check out the local entertainment venues.
What's the best hotel in Pittsfield to learn about local history?
Based on our travel knowledge, Berkshire Mountain Lodge is a top 3-star lodge for history seekers booking on Expedia, and it offers free parking and in-room kitchens. Naumkeag is a short 17-minute drive away. A couple of other options close to historic sites include Hilton Garden Inn Lenox Pittsfield and Berkshire Inn.
How many historical hotels are there in Pittsfield?
In Pittsfield, there are 64 hotel accommodations bookable on Expedia though you won’t find many designated historic hotels.
What are the must-see historical places and other sights to visit in Pittsfield?
Pittsfield is notable for landmarks like Colonial Theater, Hancock Shaker Village, and Herman Melville’s Arrowhead. Cultural venues include Berkshire Museum, Barrington Stage Company, and Crane Museum of Papermaking. A couple of additional sights to add to your agenda are Bousquet Ski Area and Berkshire Athenaeum.
What is a historic hotel like in Pittsfield?
When you book a historic hotel, you’ll spend a night or two in a place that has an officially recognized historic designation. A stately home, palace or even a lodge, old police station, or skyscraper can be turned into a historic hotel as long as it’s of special interest. Traditional architecture and period features are often preserved within the guestrooms or public spaces of historic hotels in Pittsfield, giving a historical feel.
What is the difference between a historic hotel and a heritage hotel?
“Heritage hotel” is more common in Asia and Europe, while “historic hotel” is more common in the U.S. overall though the terms are similar. The building and architecture of historic hotels tend to be the most important aspect. For a heritage hotel, it’s mainly the cultural value along with how it influenced the community.
Do historic hotels in Pittsfield have modern facilities?
Hotel interiors feature the modern conveniences and safety features you expect to find, while every effort is made to preserve historic facades and treasured traditions. Smart TVs, WiFi, updated bathroom facilities, and the amenities found at a contemporary hotel should be available at a historic hotel. Rest assured that when you select a historic hotel in Pittsfield, you won’t find yourself staying at a place that is rundown or uncomfortable.