Stockbridge Travel Guide

Tourist Guide

A river surrounded by autumn-colored trees and a forested hill.
A picnic table in a park with autumn leaves on the ground and trees with fall colors in the background.
A lake with a sunset, houses along the shore, and mountains in the background.
A stone staircase leading up to a blue arched entrance, surrounded by lush greenery and birch trees.
A nighttime view of a residential area with houses adorned with holiday lights.
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
The price is NZ$401 per night from 8 Nov to 9 Nov
NZ$401
8 Nov - 9 Nov
includes taxes & fees
Stay at this historic hotel in Stockbridge. Enjoy free Wi-Fi, free parking and 3 restaurants. Our guests praise the helpful staff in their reviews. Popular attractions ...
8.8/10 Excellent! (1,004 reviews)
"Beautiful and historic ! Dinner was delicious!"

Reviewed on 2 Nov 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
Fully refundable
The price is NZ$822 per night from 26 Nov to 27 Nov
NZ$822
26 Nov - 27 Nov
includes taxes & fees
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 ...
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Hawthorne House

Hawthorne House

Lenox MA
Stay at this holiday home in Stockbridge. Enjoy laundry facilities and air conditioning. Popular attractions Tanglewood Music Center and Frelinghuysen Morris ...
10/10 Exceptional! (3 reviews)
"We found this home to be clean, comfortable, and an excellent location to explore the Berkshires. The host was beyond helpful and accommodating. The home is cozy and well appointed. It was just my husband, myself and a friend so the separate living area downstairs afforded her extra privacy. We would ..."

Reviewed on 6 Oct 2026

Hawthorne House
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.
Hawthorne House

Hawthorne House

Lenox MA
Stay at this holiday home in Stockbridge. Enjoy laundry facilities and air conditioning. Popular attractions Tanglewood Music Center and Frelinghuysen Morris ...
10/10 Exceptional! (3 reviews)
"We found this home to be clean, comfortable, and an excellent location to explore the Berkshires. The host was beyond helpful and accommodating. The home is cozy and well appointed. It was just my husband, myself and a friend so the separate living area downstairs afforded her extra privacy. We would ..."

Reviewed on 6 Oct 2026

Hawthorne House
Historic Stockbridge Villa on 25 acres

Historic Stockbridge Villa on 25 acres

Stockbridge MA
Stay at this family-friendly villa in Stockbridge. Enjoy free Wi-Fi, private pools and a sauna. Popular attractions Tanglewood Music Center and Lenox Arts Center ...
10/10 Exceptional! (22 reviews)
"Our extended family (multiple couples, one 91 year old and 2 toddlers) spent a long weekend here for a family wedding in Lenox. The property was perfect- lots of bedrooms and bathrooms, generously sized gathering places, beautiful porches, well-equiped kitchen, and plenty of musical instruments for ..."

Reviewed on 4 Oct 2026

Historic Stockbridge Villa on 25 acres
Classic Stockbridge Cottage

Classic Stockbridge Cottage

Stockbridge MA
Stay at this holiday home in Stockbridge. Enjoy a garden, laundry facilities and patios. Popular attractions Tanglewood Music Center and Chesterwood are located ...
10/10 Exceptional! (23 reviews)
"Our family enjoyed the place and they all said it was our best experience in the Berkshire’s yet, they want to come back again next year."

Reviewed on 18 Oct 2026

Classic Stockbridge Cottage
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

Cities near Stockbridge