Stockbridge, MA

Travel Guide

A nighttime view of a residential area with houses adorned with holiday lights.
A calm lake reflecting a forest with autumn foliage.
A lake surrounded by autumn-colored trees and hills under a cloudy sky.
A white colonial-style house with black shutters, surrounded by a white picket fence and lush greenery.
A large stone house with green shutters and a steep roof, surrounded by lush trees and a well-maintained lawn.
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Fully refundable
$215 nightly
The price is $240 total per night from Sep 30 to Oct 1
$240 total
Sep 30 - Oct 1
Total with taxes and 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 ...
8.8/10 Excellent! (1,007 reviews)
"this grand old hotel is warm and welcoming — a real hub of Bershires life and history"

Reviewed on Sep 2, 2026

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

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

4.5 out of 5
26 Glendale Road, RR 183 Stockbridge MA
$358 nightly
The price is $399 total per night from Sep 28 to Sep 29
$399 total
Sep 28 - Sep 29
Total with taxes and 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 Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Inn at Stockbridge

The Inn at Stockbridge

4 out of 5
30 East Street Stockbridge MA
$396 nightly
The price is $442 total per night from Sep 13 to Sep 14
$442 total
Sep 13 - Sep 14
Total with taxes and 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! (106 reviews)
"Lovely grounds, property.. room was lovely. Delicious breakfast friendly helpful owners and staff great location"

Reviewed on Aug 30, 2026

The Inn at Stockbridge
See all 1,345 properties in Stockbridge
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

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

Historic Stockbridge Villa on 25 acres
Hawthorne House

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

Hawthorne House
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
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 ...
Vacation Village in the Berkshires
See all properties in Stockbridge
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

Norman Rockwell Museum

9.4/10 (347 reviews)
You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area.
See properties

Cities near Stockbridge

A street lined with historic buildings, including a Morgan House restaurant.

Lee

A town hall with a central dome and columns, surrounded by trees and people.

Lenox

A row of parked cars along a street lined with brick buildings, including a sign for 'Vault Studio' and 'Hotpoint'.

Great Barrington

A forested area with a calm lake and a wooden bridge.

Richmond

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