The Best Historic Hotels in The Berkshires, MA from ₩305,052 in 2026

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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 backyard with a swimming pool, lounge chairs, and a hot tub.

A covered porch with wicker furniture and hanging flower baskets.

1. The Red Lion Inn

Stockbridge

James

₩213,228

₩305,052 total

includes taxes & fees

Sep 30 - Oct 1

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Top The Berkshires Hotel Reviews

Hotel On North

10/10 Excellent

"Beautiful boutique hotel. Our room was very large with a sitting area + TV. Bed room area equally as large, also with a TV. The bathroom was gorgeous with thoughtful touches. On the marble counter was a makeup mirror with a stool so one could sit. Parking lot was in rear of hotel, secure and easy access to the lobby. Staff couldn't have been more accessible and pleasant. Highly recommend this hotel"