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Search Boutique Hotels in Stockbridge

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Check availability on Stockbridge Boutique Hotels

Tonight
20 Dec - 21 Dec
Tomorrow
21 Dec - 22 Dec
Next weekend
26 Dec - 28 Dec
In two weeks
2 Jan - 4 Jan
No exact matches found, but these alternatives could be just right

Recommended hotels in Stockbridge

Exterior
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1001)
"Old time charm and hot tub under the stars"
United States
Lori
The price is 3.947.250 ₫
5.584.832 ₫ total
includes taxes & fees
14 Jan - 15 Jan 2026
The Red Lion Inn
Suite, Private Bathroom (RedBird Suite) | View from room
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

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 10.050.225 ₫
12.157.914 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk
Best Western Plus Berkshire Hills Inn & Suites

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)
"Very friendly and good Breakfast."
United States
Jesse
The price is 2.459.926 ₫
2.747.738 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Best Western Plus Berkshire Hills Inn & Suites
Lobby
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (13)
"New hotel very nice"
United States
joel
The price is 3.552.525 ₫
3.968.170 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Element Lenox Berkshires
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1003)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is 2.107.831 ₫
2.354.447 ₫ total
includes taxes & fees
21 Dec - 22 Dec
The Yankee, Trademark Collection by Wyndham
Miscellaneous
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1003)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is 2.639.395 ₫
2.948.203 ₫ total
includes taxes & fees
14 Jan - 15 Jan 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (437)
"Nice place, easy check in"
United States
Robert
The price is 3.157.800 ₫
3.464.107 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Shaker Mill Inn
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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, (993)
"Very clean and timely and efficient and the lady who checked me in named Valerie did an amazing job and was very informative and helpful . "
United States
Dwight
The price is 2.439.400 ₫
2.724.810 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (708)
"Great hospitality "
United States
regina maria
The price is 2.815.705 ₫
3.145.142 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Lobby
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1001)
"Room was clean and comfortable; location was good with a breakfast restaurant next door. The in-house breakfast was OK, but we preferred an upgrade. Receptionist staff member was professional and pleasant. "
United States
Patrick
The price is 2.174.145 ₫
2.428.520 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Quality Inn Lee - Lenox South
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

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 Mission House. For even more to see and do, make a stop at National Shrine of the Divine Mercy, Berkshire Botanical Garden and Stockbridge Bowl.
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 temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Stockbridge are January, March, February and November, with each month seeing an average of 18 cm of snowfall.
What's the best way to get to my boutique hotel in Stockbridge?
You have a few options for travelling 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, consider renting a car to explore more sights.