Stockbridge

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
Fully refundableReserve now, pay when you stay
The price is €185 per night from 21 Jan to 22 Jan
€185
21 Jan - 22 Jan 2026
includes taxes & fees
Stay at this historic hotel in Stockbridge. Enjoy free Wi-Fi, 3 restaurants and breakfast (surcharge). Our guests praise the helpful staff in their reviews. ...
8.6/10 Excellent! (1,000 reviews)
Old time charm and hot tub under the stars

Reviewed on 15 Dec 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
The price is €395 per night from 5 Jan to 6 Jan
€395
5 Jan - 6 Jan 2026
includes taxes & fees
Stay at this luxury B&B in Stockbridge. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Tanglewood Music Center and Chesterwood are located ...
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 27 Oct 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
The price is €109 per night from 4 Jan to 5 Jan
€109
4 Jan - 5 Jan 2026
includes taxes & fees
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 ...
8.6/10 Excellent! (2,170 reviews)
Awesome for ski

Reviewed on 14 Dec 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.
A Grand property in Historic Stockbridge

A Grand property in Historic Stockbridge

Stockbridge MA
Stay at this holiday home in Stockbridge. Enjoy a garden, laundry facilities and tennis courts. Popular attractions Tanglewood Music Center and Mission House ...
9.8/10 Exceptional! (92 reviews)
We were in Stockbridge for the first time for our annual family Thanksgiving and orienteering event. Most stayed at the inn, but some rented the Taggert House as a place where family could easily be together It was perfect and so conveniently located a short and beautiful walk to town. The house ...

Reviewed on 1 Dec 2025

A Grand property in Historic Stockbridge
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 ...
8.6/10 Excellent! (2,170 reviews)
Awesome for ski

Reviewed on 14 Dec 2025

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 ...
10/10 Exceptional! (7 reviews)
Healthy food too!

Reviewed on 20 Oct 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

3
Guest rating
5 - Excellent
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5 - Excellent 0%
4 - Good
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4 - Good 0%
3 - Okay
1
3 - Okay 100%
2 - Disappointing
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1 - Terrible
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1 - Terrible 0%

3/5 - Okay

Verified traveller

I would rather have spent more time in Vermont than visiting here.