Photo by William Keller

Stockbridge Hotel Guide - Historic Hotels in Stockbridge, Massachusetts

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Check availability on Stockbridge Historic Hotels

Tonight
24 Dec - 25 Dec
Tomorrow
25 Dec - 26 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Stockbridge historic hotels

Outdoor pool, pool loungers
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"Old time charm and hot tub under the stars"
United States
Lori
The price is €180
includes taxes & fees
14 Jan - 15 Jan 2026
The Red Lion Inn
Lobby
Inn at Kenmore Hall

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 €535
includes taxes & fees
30 Dec - 31 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.
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Top Stockbridge Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"While waiting for our vallet car due to construction. The hotel staff were engaging and had personal conversations with us. Rooms were good and all staff treated us exceptional. Give them an atta boy on proformance"
Nathan 1-night trip
Posted 3 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Frequently asked questions

What should a history buff expect from a stay in Stockbridge?
A trip to the historical places in Stockbridge is probably number one on your sightseeing itinerary. Why not absorb the local colour with a visit to the bars?
What's the best accommodation in Stockbridge to be near historical sites?
Based on our travel expertise, The Red Lion Inn is a top historic hotel bookable on our site and it features free WiFi. Mission House is a short walk away.
How many historically relevant hotels will I find in Stockbridge?
In Stockbridge, there are 45 lodging options bookable on Expedia though you won't find many designated historic hotels.
What are the must-see historical places and other sights in Stockbridge?
Stockbridge is notable for landmarks like Naumkeag Museum, Mission House and Berkshire Theatre Festival. Cultural venues include Norman Rockwell Museum, Frelinghuysen Morris House and Studio and Schantz Galleries. A couple of additional sights to add to your itinerary are National Shrine of the Divine Mercy and Berkshire Botanical Garden.
What is a historic hotel like in Stockbridge?
When you choose a historic hotel, you'll sleep in a building that has a national historic designation. A palace, castle, stately home or even a lodge, pub or skyscraper can be considered a historic hotel provided that it has special significance. Traditional architecture and period features are typically preserved within the guestrooms or public spaces of these historic hotels in Stockbridge, giving a sense of history.
What is the difference between a historic hotel and a heritage hotel?
You'll often hear the term "heritage hotel" in Asia and Europe, wheareas the term "historic hotel" is more commonly used in the U.S. overall though the terms are similar. The building and architecture of a historic hotel is generally the most important aspect. For a heritage hotel, often it's the cultural value along with how it inspired the community.
Do historic hotels in Stockbridge have modern facilities?
Yes, efforts are made to preserve the historic aspects and traditions, but interiors include modern conveniences and safety features. Tourists who book a stay can expect the amenities you'd find in a hotel such as WiFi, heating and air conditioning, and updated bathroom facilities. Booking a historic hotel in Stockbridge doesn't mean you're choosing a place that's rundown.