Stockbridge

Travel Guide

A stone staircase leading up to a blue arched entrance, surrounded by lush greenery and birch trees.
A white colonial-style house with black shutters, surrounded by a white picket fence and lush greenery.
A lake with a sunset, houses along the shore, and mountains in the background.
A calm lake reflecting a forest with autumn foliage.
A lake surrounded by autumn-colored trees and hills under a cloudy sky.
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
The price is CA $223 per night from Nov 29 to Nov 30
CA $223
CA $320 total
Nov 29 - Nov 30
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 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
The price is CA $542 per night from Nov 28 to Nov 29
CA $542
CA $655 total
Nov 28 - Nov 29
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 ...
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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! (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 Oct 6, 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 vacation 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 Oct 6, 2026

Hawthorne House
Historic Stockbridge Villa on 25 acres

Historic Stockbridge Villa on 25 acres

Stockbridge MA
Book a stay at this family-friendly villa in Stockbridge. Enjoy free WiFi, private pools, and a sauna. Popular attractions Tanglewood Music Center and Lenox ...
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 Oct 4, 2026

Historic Stockbridge Villa on 25 acres
Classic Stockbridge Cottage

Classic Stockbridge Cottage

Stockbridge MA
Stay at this vacation home in Stockbridge. Enjoy a garden, laundry facilities, and patios. Popular attractions Tanglewood Music Center and Chesterwood are located ...
10/10 Exceptional! (24 reviews)
"The house was very spacious and"

Reviewed on Oct 26, 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.

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