Stockbridge Trip

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Top hotels in Stockbridge

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 ₹12,539 per night from 14 Jan to 15 Jan
₹12,539
₹18,021 total
14 Jan - 15 Jan
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
Wonderful stay in a winter wonderland that evening especially with use of the heated pool and hot tub being maintained! Loved it. Shops inside were lovely as well, bars & restaurant on-site were fun with quirky decor. Whole hotel is quirky, which is fun!

Reviewed on 26 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 ₹34,326 per night from 15 Jan to 16 Jan
₹34,326
₹41,524 total
15 Jan - 16 Jan
includes taxes & fees
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
Fully refundableReserve now, pay when you stay
The price is ₹9,345 per night from 6 Jan to 7 Jan
₹9,345
₹11,424 total
6 Jan - 7 Jan
includes taxes & fees
8.6/10 Excellent! (2,182 reviews)
A great place for our family to use as a base while skiing at Jiminy Peak! The pool was a huge hit.

Reviewed on 24 Dec 2025

Vacation Village in the Berkshires
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.

Popular places to visit

Norman Rockwell Museum

Norman Rockwell Museum

5/5(1 review)

You can spend time browsing the exhibits at Norman Rockwell Museum during your trip to Stockbridge. Wander the lakeside in this quaint area.

Norman Rockwell Museum

National Shrine of the Divine Mercy

3/5(1 review)

Learn about the local history of Stockbridge when you spend time at National Shrine of the Divine Mercy. While you're in the area, stroll along the lakeside.

National Shrine of the Divine Mercy

Naumkeag Museum

You can spend time studying the exhibits at Naumkeag Museum in Stockbridge. While you're in the area, stroll along the lakeside.

Naumkeag Museum

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