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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 4.5-star luxury B&B in Stockbridge. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Tanglewood Music Center and Chesterwood ...

9.2/10 Wonderful! (83 reviews)

My husband and I thoroughly enjoyed our stay at the Stockbridge Inn. Diane, the owner, greeted us warmly and escorted us to our room. Our accommodations were comfortable, warm and spacious and quiet enough for us to have a good night sleep. Diane was very helpful in recommending other accommodations ...

Reviewed on 12 Oct 2025

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 Colonial Plaza and Linear Park are ...

A little dated. Restaurant shut down for renovations, disappointing

Reviewed on 9 Mar 2020

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 ...

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 1,104 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.