A nighttime view of a residential area with houses adorned with holiday lights.

Find Historic Hotels in Stockbridge, MA

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Check availability on Stockbridge Historic Hotels

Tonight
Aug 23 - Aug 24
Tomorrow
Aug 24 - Aug 25
Next weekend
Aug 28 - Aug 30
In two weeks
Sep 4 - Sep 6

Our top choices for Stockbridge historic hotels

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A bar with wooden floors and shelves filled with bottles.
A backyard with a swimming pool, lounge chairs, and a hot tub.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

1. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Patricia
NT$5,075
NT$7,251 total
includes taxes & fees
Sep 23 - Sep 24
The Red Lion Inn
View all properties

Top Stockbridge Hotel Reviews

The Yankee Inn

The Yankee Inn

8/10 Good
"the room smelled like marijuana and cigarettes at initial arrival. I was in the 2nd bldg. and not able to get fresh coffee in the morning. overall, our stay was well worth it."
Luann 1-night trip
Posted 17 hours ago
The Yankee Inn
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"We loved our stay here. It’s not a modern cookie cutter experience. We loved the history and antique nature of the property."
Evan M 1-night trip
Posted 20 hours ago
The Red Lion Inn
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

8/10 Good
"Room was clean and comfortable. Always nice to have a frig and microwave."
Maureen 1-night trip
Posted 2 days ago
Howard Johnson by Wyndham Lenox
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good
"I had 2 rooms. 1 room (414) did not have a phone, the microwave didn't have power. The other room was fine. We didn't like that there was only 1 elevator working as we had to wait quite a while sometimes to go up or down. We understand that the hotel is undergoing renovations. Overall, we enjoyed our stay."
Frank 2-night trip
Posted 2 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

10/10 Excellent
"My stay at Diane’s bed and breakfast was absolutely wonderful. Diane herself is incredibly warm, welcoming, and genuinely informative — she made the entire experience feel personal and cared for. The room was quaint, cozy, and charming in that classic New England way, with comfortable beds, plenty of towels, and a generous selection of bath amenities that made settling in effortless. Breakfast was a standout: a truly amazing cook‑to‑order meal that felt both homemade and high‑end. Every dish was fresh, delicious, and clearly prepared with pride. Parking was plentiful and convenient, making arrival and departure stress‑free. Overall, this B&B is a gem — comfortable, inviting, and thoughtfully run. I’d happily return and recommend it to anyone looking for a relaxing stay."
Lisa 1-night trip
Posted 2 days ago
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Frequently asked questions

What should a history enthusiast expect from a trip to Stockbridge?
A trip to the historical places in Stockbridge is probably first on your travel itinerary. Why not absorb the local color with a visit to the bars?
What's the best place to stay in Stockbridge that's close to 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. Naumkeag Museum is a short 12-minute walk away.
How many historically relevant hotels are there in Stockbridge?
Stockbridge is home to 55 hotels and other lodging options bookable on Expedia though you won't find many designated historic hotels.
What are the top historical places and other sights to visit in Stockbridge?
Stockbridge is notable for landmarks like Naumkeag Museum, Berkshire Theatre Festival, and Mission House. Cultural venues include Norman Rockwell Museum and Schantz Galleries. A couple of additional sights to add to your agenda are National Shrine of the Divine Mercy and Berkshire Botanical Garden.
What is a historic hotel like in Stockbridge?
Guests who book a historic hotel can enjoy a vacation in a building that has an officially recognized national historic designation. A stately home, palace or even a lodge, old police station, or skyscraper can be transformed into a historic hotel as long as it's a place of special interest. Traditional architecture and period features are typically found in the communal spaces and guestrooms of such hotels in Stockbridge, giving a sense of history.
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 more common in the U.S. but overall the terms are quite similar. The architecture and building of a historic hotel tends to be what's most important. For a heritage hotel, it's often the cultural value and how it inspired the community.
Do historic hotels in Stockbridge have modern facilities?
Yes, every effort is made to preserve treasured traditions and historic facades, but interiors include modern conveniences and safety features. Visitors should expect the popular amenities you'd find in a hotel such as private rooms with updated bathroom facilities, WiFi, and more. When you book a historic hotel in Stockbridge, it doesn't mean you will stay in a place that's rundown or uncomfortable for guests.

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