Stockbridge, MA
Travel Guide
Visit Stockbridge
The Red Lion Inn
30 Main Street Stockbridge MA
The price is ￥23,806 per night from Sep 8 to Sep 9
￥23,806
￥34,495 total
Sep 8 - Sep 9
includes taxes & fees
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183 Stockbridge MA
The price is ￥57,466 per night from Sep 11 to Sep 12
￥57,466
￥69,517 total
Sep 11 - Sep 12
includes taxes & fees
Book a stay at this luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Chesterwood ...
9.2/10 Wonderful! (116 reviews)
"My stay at Diane’s bed and breakfast was absolutely wonderful. Diane herself is incredibly warm, welcoming, and genuinely informative — she made the entire experience feel personal and cared for. The room was quaint, cozy, and charming in that classic New England way, with comfortable beds, plenty ..."
Reviewed on Aug 21, 2026
The Inn at Stockbridge
30 East Street Stockbridge MA
The price is ￥59,974 per night from Sep 17 to Sep 18
￥59,974
￥70,341 total
Sep 17 - Sep 18
includes taxes & fees
Stay at this B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Lenox Arts Center are located ...
9.8/10 Exceptional! (104 reviews)
"The property and grounds are beautiful and perfectly appointed. The staff are friendly and accommodating. The room was very comfortable. The gym is small but was very functional for our purposes and we appreciated having it available. The pool is beautiful but sadly we were unable to use it as it ..."
Reviewed on Aug 25, 2026
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.
Historic Stockbridge Villa on 25 acres
Stockbridge MA
Book a stay at this family-friendly vacation home in Stockbridge. Enjoy free WiFi, private pools, and a sauna. Popular attractions Tanglewood Music Center and ...
10/10 Exceptional! (20 reviews)
"Fabulous hosts - Very informative, responsive, and accurate. House is large and typical-old-family-house quirky. The furnishings include lots of very thoughtful items such as games, thousands of books, well equiped kitchen, AC and abundant fans, etc, We found it served our multi-generational family ..."
Reviewed on Aug 8, 2026
Hawthorne House
Lenox MA
Stay at this vacation home in Stockbridge. Enjoy laundry facilities and air conditioning. Popular attractions Tanglewood Music Center and Frelinghuysen Morris ...
10/10 Exceptional! (2 reviews)
"The property is beautiful and the host was very helpful and communicative. We very much enjoyed our stay, and the location near Tanglewood is terrific."
Reviewed on Jul 30, 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (2,563 reviews)
"This particular room, the mattress on the sifabed is worn and uncomfortable. Needs a real topper, or to be replaced. I slept on the couch, not in the bed, with a sheet on it."
Reviewed on Aug 26, 2026
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.
Stay near popular Stockbridge attractions
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