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Find Boutique Hotels in Stockbridge, MA

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Check availability on Stockbridge Boutique Hotels

Tonight
5 Dec - 6 Dec
Tomorrow
6 Dec - 7 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Stockbridge Boutique Hotels

No exact matches found, but these alternatives could be just right

Recommended hotels in Stockbridge

Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1000)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is SAR 450
SAR 671 total
includes taxes & fees
5 Jan - 6 January 2026
The Red Lion Inn
Business center
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 star property
Stockbridge
9.2 out of 10, Wonderful, (110)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is SAR 1,433
SAR 1,734 total
includes taxes & fees
18 Dec - 19 Dec
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Property grounds
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stockbridge
10.0 out of 10, Exceptional, (29)
"Great stay in a well appointed house close to trails, Stockbridge center, and a quick car trip to Lenox, Great Barrington, Tanglewood, Jacobs Pillow, and Shakespeare & Co. we enjoyed the morning walks, coffee at the Lost Lamb, drinks at the Red Lion Inn, dance at Jacob’s Pillow, music at Tanglewood, ice cream at High Lawn Farm, and just that Berkshire vibe! "
United States
Phillip F.
The price is SAR 1,722
SAR 3,203 total
includes taxes & fees
6 Dec - 7 Dec
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
2 Bedrooms 1 Bath | Premium bedding, iron/ironing board, free WiFi, bed sheets
Tanglewood Suites

Tanglewood Suites

2.5 star property
Stockbridge
6.4 out of 10, (22)
"NOT A REAL LOCATION. There was nothing there. Neighbors said this was a scam. Expedia ended up helping us find a local hotel room though the location was not as good. DO NOT BOOK THIS LOCATION -- it needs to be taken off the website."
United States
Elizabeth
The price is SAR 822
SAR 822 total
includes taxes & fees
14 Dec - 15 Dec
Tanglewood Suites
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is SAR 492
SAR 549 total
includes taxes & fees
14 Dec - 15 Dec
Element Lenox Berkshires
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Great stay!"
United States
Ann
The price is SAR 335
SAR 374 total
includes taxes & fees
11 Dec - 12 Dec
The Yankee, Trademark Collection by Wyndham
Garden
Shaker Mill Inn

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (436)
"Nice place, easy check in"
United States
Robert
The price is SAR 389
SAR 426 total
includes taxes & fees
10 Dec - 11 Dec
Shaker Mill Inn
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (64)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is SAR 342
SAR 382 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1000)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
The price is SAR 351
SAR 392 total
includes taxes & fees
7 Dec - 8 Dec
Best Western Plus Berkshire Hills Inn & Suites
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very Good, (979)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is SAR 345
SAR 385 total
includes taxes & fees
12 Dec - 13 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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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Top Stockbridge Hotel Reviews

Hotel On North

Hotel On North

10/10 Excellent
"Wonderful stay, as usual. I have business in the Pittsfield area, 3 or 4 times a year and wouldn’t think of staying anywhere else. Quiet, comfortable….staff is always helpful and friendly….restaurant in the building is just another plus."
Michael 1-night trip
Posted 13 days ago
Hotel On North

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Frequently asked questions

What's there to see and do in Stockbridge?
The bars and historic landmarks are just some of the things to enjoy while you're in the area. Activities and attractions to experience around Stockbridge include Naumkeag Museum, Norman Rockwell Museum, and Frelinghuysen Morris House and Studio. For even more to see and do, make a stop at National Shrine of the Divine Mercy, Berkshire Botanical Garden, and Housatonic River.
What kind of weather should I plan for when I travel to Stockbridge?
Having a good idea of the weather in Stockbridge will help you enjoy your stay to the fullest. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Stockbridge are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's the best way to get to my boutique hotel in Stockbridge?
You have a few options for getting to and around Stockbridge. The nearest major airport is Pittsfield, MA (PSF-Pittsfield Municipal), which is located 9.6 mi (15.5 km) from the heart of the city, but Hudson, NY (HCC-Columbia County) may also be an option. If you'd like to venture out around the area, you may want to rent a car for your trip.