Stockbridge, MA

Travel Guide

A stone staircase leading up to a blue arched entrance, surrounded by lush greenery and birch trees.
A white colonial-style house with black shutters, surrounded by a white picket fence and lush greenery.
A lake with a sunset, houses along the shore, and mountains in the background.
A calm lake reflecting a forest with autumn foliage.
A lake surrounded by autumn-colored trees and hills under a cloudy sky.
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
The price is ₩210,425 per night from Nov 29 to Nov 30
₩210,425
₩301,410 total
Nov 29 - Nov 30
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 ...
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 ₩509,314 per night from Dec 6 to Dec 7
₩509,314
₩616,125 total
Dec 6 - Dec 7
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 ₩307,490 per night from Nov 15 to Nov 16
₩307,490
₩360,632 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 ...
9/10 Wonderful! (1,269 reviews)
"Everything was great!"

Reviewed on Nov 12, 2026

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.

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