Find Historic Hotels in Pittsfield, MA

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Check availability on Pittsfield Historic Hotels

Top Pittsfield Historic Hotels

Hotel On North
Food and drink

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (743)
"Great boutique hotel"
The price is ₩260,283
₩290,737 total
includes taxes & fees
Jul 21 - Jul 22
Hotel On North
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (821)
"Very convenient location, downtown, short drive to local attractions "
The price is ₩158,373
₩176,902 total
includes taxes & fees
Jul 30 - Jul 31
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is ₩296,447
₩331,138 total
includes taxes & fees
Jul 27 - Jul 28
Hilton Garden Inn Lenox Pittsfield
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1012)
"Very nice stay"
The price is ₩174,417
₩194,823 total
includes taxes & fees
Jul 27 - Jul 28
Best Western Plus Berkshire Hills Inn & Suites
Berkshire Inn
1 bedroom, desk, iron/ironing board, free WiFi

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (779)
"The motel was nicely done and clean. The beds were comfortable "
The price is ₩137,702
₩153,815 total
includes taxes & fees
Jul 20 - Jul 21
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.

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 72 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, Herman Melville's Arrowhead, and Hancock Shaker Village. 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 Housatonic River.
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.