Stockbridge

Travel Guide

A river surrounded by autumn-colored trees and a forested hill.
A picnic table in a park with autumn leaves on the ground and trees with fall colors in the background.
A lake with a sunset, houses along the shore, and mountains in the background.
A stone staircase leading up to a blue arched entrance, surrounded by lush greenery and birch trees.
A nighttime view of a residential area with houses adorned with holiday lights.
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
The price is P9,931 per night from Nov 17 to Nov 18
P9,931
P14,226 total
Nov 17 - Nov 18
includes taxes & fees
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! (1,012 reviews)
"The Red lion Inn is a unique historical stay. The hotel is charming with so many historical items to look at every turn. There are plenty of cute shops and great hiking trails right down the road."

Reviewed on Nov 9, 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 P24,080 per night from Nov 26 to Nov 27
P24,080
P29,129 total
Nov 26 - Nov 27
includes taxes & fees
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 ...
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 P15,307 per night from Nov 15 to Nov 16
P15,307
P17,953 total
Nov 15 - Nov 16
includes taxes & fees
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 ...
9.6/10 Exceptional! (110 reviews)
"My husband and I stayed in one of the cottages on the property. It was very quaint, quiet and clean! The inclusive full breakfast is served hot and delicious. The presentation is amazing and the jam is homemade! You can actually purchase jars of the jam to take home, which we did! Gluten free breakfast ..."

Reviewed on Nov 8, 2026

The Inn at 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 ...
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 ...
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 ...
8.4/10 Very Good! (157 reviews)
"liked it was clean . furniture is dated. Roads need repair . too many potholes"

Reviewed on Nov 2, 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