A river surrounded by autumn-colored trees and a forested hill.

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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan
No exact matches found, but these alternatives could be just right

Recommended hotels in Stockbridge

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

1. The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,009 reviews)
"Great location - hotel has an excellent dining room and there are several other restaurants within easy walking distance from hotel. A historic, old hotel with lots of curated artwork and history."
United States
Lisabeth
The price is AED 579
AED 829 total
includes taxes & fees
12 Nov - 13 Nov
The Red Lion Inn
Front of property

2. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (108 reviews)
"Wonderful place… clean, cosy room, comfy bed, friendly staff, great breakfast. Delightful location near Norman Rockwell museum."
United States
Kimberly
The price is AED 981
AED 1,151 total
includes taxes & fees
8 Nov - 9 Nov
The Inn at Stockbridge
A two-story house with a brick entrance and a white facade.

3. 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
9.4 out of 10, Exceptional, (120 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is AED 1,403
AED 1,697 total
includes taxes & fees
26 Nov - 27 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A two-story house with a front porch, surrounded by a garden with various plants and rocks.

4. 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, (42 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveler
The price is AED 1,690
AED 3,028 total
includes taxes & fees
23 Nov - 24 Nov
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Dining

5. Garden Gables

Garden Gables
4.0 star property
Lenox
10.0 out of 10, Exceptional, (2 reviews)
"Lovely place!"
United States
Eyee
The price is AED 480
AED 803 total
includes taxes & fees
8 Nov - 9 Nov
Garden Gables
A four-poster canopy bed with a wooden frame and white bedding, a small bedside table with a lamp, and a large window with a view of the city.

6. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"The location was good for our trip."
United States
Basil
The price is AED 415
AED 464 total
includes taxes & fees
20 Nov - 21 Nov
The Yankee Inn
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

7. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,000 reviews)
"Amazing place, clean, staff is awesome , amazing location , amazing views! Free breakfast, free coffee bar , free gym and the best it’s pet friendly !"
United States
Gustavo
The price is AED 397
AED 443 total
includes taxes & fees
1 Dec - 2 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

8. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
3.5 star property
South Lee
9.2 out of 10, Wonderful, (1,002 reviews)
"Nice place to stay"
United States
Michael
The price is AED 406
AED 525 total
includes taxes & fees
8 Nov - 9 Nov
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.

9. 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, (854 reviews)
"Always a pleasurable stay. The rooms are clean, the amenities are appreciated, and the staff very attentive. Great location and as a single traveler I always feel safe staying here."
United States
Cynthia
The price is AED 305
AED 341 total
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A reception area with a fireplace, seating, and a doormat with the logo "Quality".

10. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.6 out of 10, Excellent, (1,001 reviews)
"Perfect for a travel stop-over."
United States
James
The price is AED 312
AED 348 total
includes taxes & fees
2 Dec - 3 Dec
Quality Inn Lee - Lenox South
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

11. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (941 reviews)
"Easy access to everywhere we went. Clean"
United States
Phillip
The price is AED 220
AED 246 total
includes taxes & fees
8 Nov - 9 Nov
Monument Mountain Motel
A large house with a balcony and a grassy yard.

12. The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (639 reviews)
"Wonderful place to stay and still enjoy the amenities at the Red Lion Inn"
United States
Linda
The price is AED 304
AED 340 total
includes taxes & fees
9 Nov - 10 Nov
The Little Lion
A calm lake at dusk with a wooden dock and two chairs facing the water.

13. Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
9.8 out of 10, Exceptional, (27 reviews)
"excellent lakeside view"
United States
mike
The price is AED 401
AED 448 total
includes taxes & fees
8 Nov - 9 Nov
Berkshire Lake Lodge
A red building with a sign reading "Shaker Mill Inn."

14. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (483 reviews)
"Loved the location, fireplace and vibe"
United States
Mahadeva
The price is AED 533
AED 584 total
includes taxes & fees
8 Nov - 9 Nov
Shaker Mill Inn
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

15. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (821 reviews)
"Nice view and location for fall color."
United States
Md
The price is AED 590
AED 659 total
includes taxes & fees
10 Nov - 11 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

16. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,067 reviews)
"Very nice place beautiful view"
United States
Brian
The price is AED 386
AED 431 total
includes taxes & fees
17 Nov - 18 Nov
Berkshires Untold
A two-story building with a sign reading "Chambéry Inn".

17. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (390 reviews)
"An absolutely perfect getaway spot! Beautiful rooms, great service, and an ideal location. Highly recommend and we will be going back."
United States
Alexandra
The price is AED 681
AED 760 total
includes taxes & fees
10 Nov - 11 Nov
Chambery Inn
A building entrance with a large planter with purple flowers and a small tree.

18. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (981 reviews)
"Very nice hotel"
United States
Philip
The price is AED 426
AED 476 total
includes taxes & fees
29 Nov - 30 Nov
Hotel On North
An indoor swimming pool with clear water, tiled floors, and a blue wall.

19. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (257 reviews)
"The room was clean and well kept, breakfast was amazing!"
United States
Ruth
The price is AED 378
AED 423 total
includes taxes & fees
6 Dec - 7 Dec
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

20. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Downtown Great Barrington
8.6 out of 10, Excellent, (1,003 reviews)
"Our room was spotless and the staff was helpful and welcoming!"
United States
Lynne
The price is AED 278
AED 310 total
includes taxes & fees
29 Nov - 30 Nov
Quality Inn Great Barrington
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Very centrally located. Right next to a good little market. Very reasonable price for an apartment like room."
Holly 3-night trip
Posted 23 hours ago
Berkshire Mountain Lodge

Frequently asked questions

What can I expect from a resort vacation in Stockbridge?
You deserve a getaway, and a resort is just the place to treat yourself to the services and amenities you need for a relaxing time in Stockbridge. One of the comfortable resorts in the area might be just what you're searching for, whether you want an amazing pool, a state-of-the-art fitness center, or nightly entertainment options.
What's the best resort for my stay in Stockbridge?
Our top-rated resorts near Stockbridge: In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants - Ski resort right by Jiminy Peak Mountain Resort. 18.6 mi (29.9 km) from Stockbridge. Has ski-in/ski-out access, a fitness center, and a garden. COZY CABIN IN BERKSHIRES RESORT. - Ski resort right by Jiminy Peak Mountain Resort. 18.6 mi (30 km) from Stockbridge. Enjoy the ski-in/ski-out access, fitness center, and beach sun loungers. Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out - Ski resort, 5-minute walk from Jiminy Peak Mountain Resort. 18.7 mi (30.1 km) from Stockbridge. Access to ski-in/ski-out access, a fitness center, and an indoor pool.
What can I do in Stockbridge?
Travelers enjoy visiting the historic sites and other landmarks in Stockbridge, and also have good things to say about its bars. Learn about the local history at monuments like National Shrine of the Divine Mercy, or bring the kids to Berkshire Botanical Garden for some family fun. Additional attractions in the area include Naumkeag Museum and Norman Rockwell Museum.
What's the weather like in Stockbridge?
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 and around Stockbridge?
Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 9.6 mi (15.5 km) away from the heart of the city. Otherwise, you can search for flights to Hudson, NY (HCC-Columbia County), which is 20 mi (32.3 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.

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