Photo by Photo courtesy of Berkshire Visitors Bureau

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Top Luxury The Berkshires Hotels

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

26 Glendale Road, RR 183 Stockbridge MA

46 min drive from Jiminy Peak Mountain Resort

Spoil yourself with classy accommodations at The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, where you'll enjoy amenities ...

9.2/10 Wonderful! (110 reviews)

It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!

Reviewed on Oct 27, 2025

The Orchards Hotel

222 Adams Rd Williamstown MA

25 min drive from Jiminy Peak Mountain Resort

Treat yourself to a luxury stay at The Orchards Hotel, where you can enjoy amenities like massage services, pillowtop beds, and more. The outdoor pool, restaurant, ...

Lantern House Motel

256 Stockbridge Road Great Barrington MA

58 min drive from Jiminy Peak Mountain Resort

Lantern House Motel awaits for a deluxe vacation. Popular amenities include an outdoor pool and a garden.

8.2/10 Very Good! (455 reviews)

Avoid staying here if you can.

The fact that they require a vaccine card should be mentioned in their Hotels.com profile. Luckily for me I had it in my car. I don't mind if some hotel owners want to require it, but it should be pretty clearly stated. The owner told me that I didn't need to use the air conditioner, that I should ...

Reviewed on Nov 22, 2021

See all 1,102 properties in The Berkshires

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.