Stockbridge Holiday Packages

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Stockbridge Accommodation

It can sometimes be difficult trying to figure out which is the right place to stay when faced with so much choice. There are 37 accommodations in Stockbridge. Time to start looking.

Let's face it — you've earned this getaway, right? Why not splurge a little and treat yourself to a couple of nights in a classy room at the Blantyre (16 Blantyre Rd) or the Hampton Terrace Inn (91 Walker Street)? Wanting to keep more dollars in your pocket? With awesome budget options such as the Gateways Inn & Restaurant (51 Walker St) and The Briarcliff Motel (506 Stockbridge Road) to select from, you won't be left out in the cold.

Holidays to Stockbridge

Before you wave goodbye to the cat and climb in that taxi to the airport, it's good to know one or two things about where you're headed. Keep reading for a few useful Stockbridge pointers.

Want to visualise where you'll be based? Stockbridge is situated 180 kilometres north of the notable city of New York.

If you're holidaying with the young ones and they're starting to get a little antsy, why not quiz them to see if they can tell you what the population of this area of The Berkshires is? (It's roughly 2 000 in case you're wondering yourself.)

Top Stockbridge hotels

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 AU$696 per night from 5 Jan to 6 Jan
AU$696
5 Jan - 6 Jan 2026
includes taxes & fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood: Luxury bed & breakfast with free breakfast and free WiFi. Located near ...
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

Opens in a new windowThe Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
The price is AU$311 per night from 14 Jan to 15 Jan
AU$311
14 Jan - 15 Jan 2026
includes taxes & fees
The Red Lion Inn: Pet-friendly hotel with free WiFi and an outdoor pool. Located in the historical district.
We had a very nice experience staying at the Red Lion Inn. Our room was upgraded when checking in which was a nice surprise. The hotel was beautifully decorated for the season. We loved the cozy feel of the fireplace in the lobby especially on such a cold day.

Reviewed on 12 Dec 2025

Opens in a new windowThe Red Lion Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
The price is AU$191 per night from 4 Jan to 5 Jan
AU$191
4 Jan - 5 Jan 2026
includes taxes & fees
Vacation Village in the Berkshires: Family-friendly condo with free WiFi and free parking. Located near skiing.
Awesome for ski

Reviewed on 14 Dec 2025

Opens in a new windowVacation Village in the Berkshires
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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.