Search Historic Hotels in Pittsfield

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Pittsfield Historic Hotels

Tonight
7 Dec - 8 Dec
Tomorrow
8 Dec - 9 Dec
Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec

Top Pittsfield Historic Hotels

Outdoor pool, pool loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1000)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is ₹13,809
₹19,446 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Red Lion Inn
Lobby
Inn at Kenmore Hall

Inn at Kenmore Hall

3.0 star property
Richmond
10.0 out of 10, Exceptional, (27)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is ₹38,247
₹41,957 total
includes taxes & fees
16 Dec - 17 Dec
Inn at Kenmore Hall
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.
View all properties

Top Pittsfield Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"It was all well cared for."
David 3-night trip
Posted 3 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Explore a world of travel with Expedia

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.
How many historical hotels will I find in Pittsfield?
In Pittsfield, you'll find 74 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.