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
$214 nightly
The price is $239 total per night from Sep 9 to Sep 10
$239 total
Sep 9 - Sep 10
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! (1,017 reviews)
"This is an old inn. It’s elegant, fun and very comfortable. Lots of dark, antique furniture and communal card games. The staff is friendly and some have been there many years. Many of the guests return year after year. If that’s what you’re looking for, you will love it. I do. If you are looking ..."

Reviewed on Aug 11, 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 Aug 25 to Aug 26
$399 total
Aug 25 - Aug 26
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! (114 reviews)
"Very lovely beautiful Room and property The outside pool was not available"

Reviewed on Jul 30, 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
$421 nightly
The price is $471 total per night from Sep 7 to Sep 8
$471 total
Sep 7 - Sep 8
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! (101 reviews)
"Our room was very clean and comfortable - exactly what we needed to rest well. Breakfast was excellent and we felt well taken care of. We are grateful for the friendly and welcoming hosts and their staff who listened to every need and graciously provided for us. We’ll definitely return for another ..."

Reviewed on Aug 3, 2026

The Inn at Stockbridge
See all 1,330 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! (19 reviews)
"I can not say enough about how wonderful this stay was! The hosts had great communication, the house was spotless (and this is a LARGE house), they had every possible thing you could need and the best part was all the cabinets were labeled so we didn't have to hunt for things!! The pool was spotless, ..."

Reviewed on Jul 27, 2026

Historic Stockbridge Villa on 25 acres
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 ...
8.8/10 Excellent! (2,520 reviews)
"Beautiful location and pricey, but less expensive than most places in the area. It is spacious with a kitchen that we did not use, the rooms are very dated. You can hear through the walls very well. Didn’t use pool because it was so crowded."

Reviewed on Aug 11, 2026

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,060 reviews)
"Good location, nice room, easy access"

Reviewed on Aug 10, 2026

Berkshire Mountain Lodge
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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