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
The price is NT$4,997 per night from Sep 30 to Oct 1
NT$4,997
per night
Sep 30 - Oct 1
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! (1,014 reviews)
"The Inn is very welcoming with a broad front porch filled with wicker chairs and rockers. Inside there are many sitting rooms, a restaurant and tavern, gift and floral shops and access to an outdoor pool. Well loved antiques are everywhere for comfortable seating throughout the property. Rooms facing ..."

Reviewed on 2026/9/8

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 NT$10,417 per night from Sep 28 to Sep 29
NT$10,417
per night
Sep 28 - Sep 29
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! (117 reviews)
"My room was terribly dark though thankfully, very clean and bed was comfortable. Barely adequate AC. You can’t get a cup of coffee before 8am, no Keurig or tea station. The driveway needed maintenance, be careful driving in, The Innkeeper has a strange affect, so I wasn’t sure if we were communicating. ..."

Reviewed on 2026/9/6

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
The price is NT$11,893 per night from Sep 14 to Sep 15
NT$11,893
per night
Sep 14 - Sep 15
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! (106 reviews)
"Lovely grounds, property.. room was lovely. Delicious breakfast friendly helpful owners and staff great location"

Reviewed on 2026/8/30

The Inn at Stockbridge
See all 1,345 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.
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! (2,618 reviews)
"Great location, fair price, clean and spacious"

Reviewed on 2026/9/8

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! (1,134 reviews)
"Staff is very friendly and helpful."

Reviewed on 2026/9/7

Berkshire Mountain Lodge
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 WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and The Mount are located ...
8.6/10 Excellent! (149 reviews)
"Our unit was very comfortable for 2 senior couples. We were only there for the weekend so we didn’t use any of the amenities but, the property is lovely."

Reviewed on 2026/9/4

The Ponds at Foxhollow
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.
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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 mountainous landscape with a lake and dense forests.

West Stockbridge