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

Spacious Living, Covered Porch & Forest Setting | Beaver Creek by AvantStay

Spacious Living, Covered Porch & Forest Setting | Beaver Creek by AvantStay

Stockbridge MA
Spacious Living, Covered Porch & Forest Setting | Beaver Creek by AvantStay: Holiday home with free WiFi and parking.
The house is large with great space inside and out. The beds and pillows were comfortable and the kitchen is functional. The location in between Stockbridge and Lenox was great. Cons: ladybug infestation upstairs was pretty disgusting, the dishwasher is in an odd location, and 2 of the doors accessible ...

Reviewed on 13 Apr 2026

Opens in a new windowSpacious Living, Covered Porch & Forest Setting | Beaver Creek by AvantStay
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 AU$303 per night from 18 May to 19 May
AU$303
18 May - 19 May
includes taxes & fees
The Red Lion Inn: Pet-friendly hotel with free WiFi and free parking. Located near skiing.
Lovely and historic property. Friendly staff and very comfortable room. Dinner and breakfast were wonderful. We are repeat visitors.

Reviewed on 11 May 2026

Opens in a new windowThe 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 AU$517 per night from 25 May to 26 May
AU$517
25 May - 26 May
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 the ...
Opens in a new windowThe Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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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.