A person snowboarding down a snowy slope.

Find Historic Hotels in The Berkshires, MA

  • 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 The Berkshires Historic Hotels

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

Our top choices for The Berkshires historic hotels

1. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
James
AED 579
AED 829 total
includes taxes & fees
30 Sep - 1 Oct
The Red Lion Inn
View all properties

Top The Berkshires Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Good place"
Nicholas 2-night trip
Posted 12 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 15 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 20 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 3 days ago
Howard Johnson by Wyndham Lenox

Explore a world of travel with Expedia