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

Stockbridge Hotel Guide - Historic Hotels in Stockbridge, Massachusetts

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Check availability on Stockbridge Historic Hotels

Tonight
22 Sept - 23 Sept
Tomorrow
23 Sept - 24 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

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 covered porch with wicker furniture and hanging flower baskets.
A backyard with a swimming pool, lounge chairs, and a hot tub.

1. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
James
€197
includes taxes & fees
30 Sept - 1 Oct
The Red Lion Inn
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.
A spacious living area with a stone fireplace, comfortable seating, and a dining area.
A snow-covered outdoor area with a fire pit, tables, and chairs, indicating a winter resort setting.
A two-story building with a swimming pool, outdoor seating, and a sign for 'John Harvard's Restaurant & Brewery'.

2. Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Hancock
United States
Kristina L.
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
A two-story house with a balcony, a deck, and a view of the surrounding forest.
A modern kitchen with white cabinets and a built-in knife block.
A kitchen with wooden floors, a central island, a stainless steel refrigerator, and pendant lighting.
A spacious living room with a high ceiling, a fireplace, and a staircase leading to an upper level.

3. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
United States
Anne S.
€667
includes taxes & fees
18 Oct - 19 Oct
Gorgeous Mountain Views Retreat: Family & Nature
View all properties

Top Stockbridge Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Good place"
Nicholas 2-night trip
Posted 5 hours ago
Quality Inn Great Barrington
The Yankee Inn

The Yankee Inn

10/10 Excellent
"The room was spacious, clean and comfortable. I will definitely stay there again."
William 2-night trip
Posted 8 hours ago
The Yankee Inn
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"This is a wonderful, historic inn. Check out the Red Lion Den for music. We heard a terrific local group. We ate in the Tavern and the food was tasty. This is not a luxurious place. It dates back to the 1700s. But it is really charming. My friends and I stayed in a suite in an out building. We had a low-ceiled living room downstairs, which was a. great place to talk and catch up. The bedroom situation was a little funky because the bathroom was right next to the bed in one of two sleeping areas upstairs and the door really squeaked when it opened and closed. But that was about our only complaint. I'd be delighted to return."
Gerald 1-night trip
Posted 14 hours ago
The Red Lion Inn
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"Good"
Kauan 1-night trip
Posted 2 days ago
Howard Johnson by Wyndham Lenox

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. Naumkeag Museum is a short 12-minute walk away.
How many historically relevant hotels will I find in Stockbridge?
In Stockbridge, there are 55 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, Berkshire Theatre Festival and Mission House. Cultural venues include Norman Rockwell Museum 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.