Stockbridge, MA

Travel Guide

Stockbridge
Photo by William Keller
Photo by William Keller
Photo by William Keller
Photo by Adnan Kakazai
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
$185 nightly
The price is $207 total per night from Dec 15 to Dec 16
$207 total
Dec 15 - Dec 16
Total with taxes and fees
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
8.8/10 Excellent! (1,002 reviews)
I love the ambience - historic and comfortable and excellent food.

Reviewed on Nov 5, 2025

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
$414 nightly
The price is $462 total per night from Nov 30 to Dec 1
$462 total
Nov 30 - Dec 1
Total with taxes and fees
Stay at this 4.5-star luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Chesterwood ...
9.2/10 Wonderful! (85 reviews)
It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!

Reviewed on Oct 27, 2025

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
$119 nightly
The price is $133 total per night from Nov 15 to Nov 16
$133 total
Nov 15 - Nov 16
Total with taxes and fees
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (2,131 reviews)
Good

Reviewed on Nov 10, 2025

Vacation Village in the Berkshires
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 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (2,131 reviews)
Good

Reviewed on Nov 10, 2025

Vacation Village in the Berkshires
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3 out of 5
37 Corey Rd, Hancock, MA
Stay at this 3-star ski condo in Hancock. Enjoy free parking, 2 restaurants, and 2 hot tubs. Our guests praise the property condition in our reviews. Popular ...
8.2/10 Very Good! (984 reviews)
This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the ...

Reviewed on Oct 5, 2025

Jiminy Peak Mountain Resort
Huttopia Berkshires

Huttopia Berkshires

1 out of 5
312 Kittle Rd, Williamstown, MA
Stay at this campground in Williamstown. Enjoy free parking, breakfast (surcharge), and a picnic area. Popular attractions Jiminy Peak Mountain Resort and Mountain ...
10/10 Exceptional! (7 reviews)
Healthy food too!

Reviewed on Oct 20, 2025

Huttopia Berkshires
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.

Popular places to visit

Reviews of Stockbridge

4.5
Top Destination
5 - Excellent
26
5 - Excellent 62%
4 - Good
12
4 - Good 29%
3 - Okay
2
3 - Okay 5%
2 - Disappointing
2
2 - Disappointing 5%
1 - Terrible
0
1 - Terrible 0%

4/5 - Good

Verified traveler

Stockbridge has always been a small, sweet, and welcoming town to visit. This is its constant charm.

3/5 - Okay

Verified traveler

It seemed kind of boring. I walked around several times, since I am a walker.

5/5 - Excellent

Verified traveler

A visit to the healing arts center at Kripalu for bodywork or a facial is highly recommended. It makes your visit even more relaxing!

5/5 - Excellent

Verified traveler

lovely

4/5 - Good

Verified traveler

It is very safe and the city is beautiful.

4/5 - Good

Verified traveler

Could use a few shops like Lenox

Cities near Stockbridge

Explore a world of travel with Expedia