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Find Historic Hotels in The Berkshires, MA

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Check availability on The Berkshires Historic Hotels

Tonight
Oct 18 - Oct 19
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Oct 19 - Oct 20
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Oct 23 - Oct 25
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Oct 30 - Nov 1

Our top choices for The Berkshires 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 swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A covered porch with wicker furniture and hanging flower baskets.

1. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Stephan
NT$5,104
NT$7,311 total
includes taxes & fees
Nov 4 - Nov 5
The Red Lion Inn
View all properties

Top The Berkshires Hotel Reviews

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"We had a fantastic one-night stay at The Cornell Inn! From the moment we checked in—where we were greeted with delicious brownies in the lobby—the staff were super nice and welcoming. They truly went above and beyond to make sure we had everything we needed. We stayed in K11 - The Edith Wharton Room, which featured a comfortable queen bed and was fully equipped with all the essentials, plus a lovely bottle of wine waiting for us. The hotel is spotlessly clean, and the decoration throughout is absolutely beautiful and cozy. The staff did a wonderful job with breakfast. Everything was fresh and delicious—do not skip it! We also loved the outside area. It was so relaxing to sit in a rocker chair, surrounded by beautiful vegetation, watching the fish. We highly recommend this inn and can't wait to return!"
Yoanka 1-night trip
Posted 3 hours ago
The Cornell Inn, Lenox & The Berkshires
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"Everything about the property was excellant, clean,helpful Thank you very much"
Debra 1-night trip
Posted 3 hours ago
Hampton Inn & Suites Berkshires-Lenox
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"-"
Serena 1-night trip
Posted 7 hours ago
Quality Inn Great Barrington
The Yankee Inn

The Yankee Inn

8/10 Good
"Lovely, super clean unit with nice furnishings, however, the dining chair cushions need a good cleaning as the dirt could be seen. There also was candy/gum stuck to one of the cushions and another cushion was completely loose from the chair. There was mention of a "two-burner hotplate" in the description, but the photos showed a two-burner electric stove top. What actually is there is a two-burner infared hotplate. Instructions on how to use it is posted on the wall above the sink, not on the wall above the hotplate. Unfortunately, we were assigned an end unit in Building #13, which is currently being renovated. There was a family occupying the unit above us. The children ran up and down the stair and allowed the outside door to slam each and every time until late in the evening. No noise during quiet hours though. :o)"
Julio 1-night trip
Posted 7 hours ago
The Yankee Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Would stay here again for sure"
Jennifer 1-night trip
Posted 21 hours ago
Hotel Downstreet, an Ascend Collection Hotel

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