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
$182 nightly
The price is $204 total per night from Jan 8 to Jan 9
$204 total
Jan 8 - Jan 9
Total with taxes and fees
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (1,005 reviews)
Absolutely fabulous!

Reviewed on Jan 5, 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
$414 nightly
The price is $462 total per night from Jan 21 to Jan 22
$462 total
Jan 21 - Jan 22
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 Chesterwood and Norman Rockwell Museum ...
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
$126 nightly
The price is $141 total per night from Jan 11 to Jan 12
$141 total
Jan 11 - Jan 12
Total with taxes and fees
Book a stay at this 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! (2,200 reviews)
Clean rooms, chimney did not work

Reviewed on Jan 4, 2026

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
Book a stay at this 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! (2,200 reviews)
Clean rooms, chimney did not work

Reviewed on Jan 4, 2026

Vacation Village in the Berkshires
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
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3 out of 5
37 Corey Rd Hancock MA
Book a stay at this 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! (988 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
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

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