The Berkshires Luxury Holidays 2026

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

12 min drive from Tanglewood Music Center

Stay at this luxury B&B in Stockbridge. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Tanglewood Music Center and Chesterwood are located ...

9.2/10 Wonderful! (114 reviews)

"Very lovely beautiful Room and property The outside pool was not available"

Reviewed on 30 Jul 2026

The Orchards Hotel

222 Adams Rd Williamstown MA

59 min drive from Tanglewood Music Center

Stay at this business-friendly hotel in Williamstown. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Massachusetts Museum of Contemporary ...

Lantern House Motel

256 Stockbridge Road Great Barrington MA

24 min drive from Tanglewood Music Center

Stay at this motel in Great Barrington. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Housatonic River and Lake Mansfield Park are located ...

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 22 Nov 2021

See all 1,086 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.