Pittsfield Hotel Guide - Historic Hotels in Pittsfield, Massachusetts

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Check availability on Pittsfield Historic Hotels

Top Pittsfield Historic Hotels

Hotel On North
Front of property – evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (743)
"Great boutique hotel"
The price is €180
includes taxes & fees
21 Jul - 22 Jul
Hotel On North
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (816)
"Very convenient location, downtown, short drive to local attractions "
The price is €110
includes taxes & fees
13 Jul - 14 Jul
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, (636)
"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 €214
includes taxes & fees
13 Jul - 14 Jul
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, (1008)
"Great place to stay "
The price is €113
includes taxes & fees
13 Jul - 14 Jul
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 €95
includes taxes & fees
10 Jul - 11 Jul
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 buff expect from a stay in Pittsfield?
Sights with historical relevance in Pittsfield are probably at the top of your travel itinerary. 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 will I find in Pittsfield?
In Pittsfield, you'll find 72 hotels and other lodging options bookable on Expedia but not many designated as 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 itinerary are Bousquet Ski Area and Housatonic River.
What is a historic hotel like in Pittsfield?
By booking a historic hotel, guests can spend a night or two someplace that has an officially recognised historic designation. A castle, a palace or even a pub or an old police station can be turned into a historic hotel as long as it's a place of special interest. Traditional architecture and period features can be admired in the guestrooms or communal spaces of such hotels in Pittsfield, giving a real sense of character.
What is the difference between a historic hotel and a heritage hotel?
"Heritage hotel" is a term often used in Asia and Europe, while "historic hotel" is a term often used in the U.S. though overall the terms are quite similar. The architecture and building of historic hotels tend to be what's most significant. For a heritage hotel, it's mainly the cultural value as well as how it influenced the community.
Do historic hotels in Pittsfield have modern facilities?
Hotel interiors feature the modern conveniences and safety features you might expect, but every effort is made to preserve historic facades and treasured traditions. Private rooms with updated bathroom facilities, heating and air conditioning, free and fast Internet, and the normal amenities found in any hotel should be available at a historic hotel. When you choose a historic hotel in Pittsfield, don't worry that you'll be staying at a place that's uncomfortable or rundown.