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 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$389 per night from 6 Aug to 7 Aug
AU$389
6 Aug - 7 Aug
includes taxes & fees
The Red Lion Inn: Pet-friendly hotel with free WiFi and an outdoor pool. Located in the historical district.
good for me not for my wife
"I loved the early 20th century atmosphere, my wife disliked it. food was excellent. bed seemed lumpy and soft but we slept well"

Reviewed on 30 Jul. 2025

The Red Lion Inn
Tanglewood Suites

Tanglewood Suites

2.5 out of 5
MA-102, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is AU$416 per night from 7 Aug to 8 Aug
AU$416
7 Aug - 8 Aug
includes taxes & fees
Tanglewood Suites: Bed & breakfast with free breakfast and free WiFi. Located in the mountains.
Like a stay at granny’s house
"Portion of hosts home, separate and available for rent. Heating system not efficient and took some work to sort out how to keep all areas of the unit comfortably heated. Beds clean and comfortable. Overall cleanliness was good. Bath facilities are an addition to existing structure and sufficient, ..."

Reviewed on 19 Feb. 2024

Tanglewood Suites
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$733 per night from 19 Aug to 20 Aug
AU$733
19 Aug - 20 Aug
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 ...
"Very expensive for a small room. My son and I could barely sleep in this remote quiet place. Staffs were very friendly."

Reviewed on 2 Nov. 2024

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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