Stockbridge Travel Guide

Tourist 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
The price is AU$305 per night from 8 July to 9 July
AU$305
8 July - 9 July
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)
"Staff was great. Cool place - so historic"

Reviewed on 30 June 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
The price is AU$580 per night from 15 July to 16 July
AU$580
15 July - 16 July
includes taxes & fees
Stay at this luxury B&B in Stockbridge. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Norman Rockwell Museum and National Shrine of ...
9.2/10 Wonderful! (112 reviews)
"Our stay at The Inn was wonderful. Diane and staff could not have been more welcoming or helpful with great suggestions. Shopping and picnic supplies were spot on! Breakfast was delicious and more than plentiful. The pool was not available at this time, but what a beautiful setting. We’ll stay here ..."

Reviewed on 30 June 2026

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

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
The price is AU$258 per night from 6 July to 7 July
AU$258
6 July - 7 July
includes taxes & fees
Stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
9.2/10 Wonderful! (1,010 reviews)
"Breakfast included is very good. We stayed in the original brick building which needs improvement."

Reviewed on 30 June 2026

The Yankee Inn
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.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff in their ...
8.8/10 Excellent! (2,412 reviews)
"Staff was super friendly, splash pad was being renovated so that wasn’t available m.. we had fun but hate that check in is so late and check out so early!"

Reviewed on 30 June 2026

Vacation Village in the Berkshires
Huttopia Berkshires

Huttopia Berkshires

1 out of 5
312 Kittle Rd Williamstown MA
Stay at this campsite in Williamstown. Enjoy free parking, breakfast (surcharge) and a picnic area. Popular attractions Jiminy Peak Mountain Resort and Mountain ...
9.6/10 Exceptional! (11 reviews)
"We stayed in a Sierra Tiny House for 3 nights in June 2026. The house was very clean, compact but with everything you need, including a fully equipped kitchen. You should be aware that the kid's room has a triple bunk - it might be a challenge if you had an older teen or adult staying in there because ..."

Reviewed on 29 June 2026

Huttopia Berkshires
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7 Lenox MA
Stay at this aparthotel in Lenox. Enjoy free Wi-Fi, free parking and a fitness centre. Popular attractions Tanglewood Music Center and National Shrine of the ...
8.6/10 Excellent! (141 reviews)
"I had not visited the Ponds for 30 years. It has not gracefully aged. Condo unit has not been updated since it was built in the early 70s and it shows. Drafty and slightly damaged doors, slow drains in the bathrooms, furniture and rugs that show damage and age, and a clubhouse in need of updating. ..."

Reviewed on 9 Feb 2026

The Ponds at Foxhollow
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