A nighttime view of a residential area with houses adorned with holiday lights.

Search Resorts in Stockbridge

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
14 Aug - 16 Aug
In two weeks
21 Aug - 23 Aug
In one month
4 Sep - 6 Sep
In two months
2 Oct - 4 Oct
No exact matches found, but these alternatives could be just right

Recommended hotels in Stockbridge

Property grounds

1. The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,010 reviews)
"I always enjoy the Red Lion inn."
United States
Merideth
The price is AED 630
AED 887 total
includes taxes & fees
7 Sep - 8 Sep
The Red Lion Inn
Suite, Private Bathroom (RedBird Suite) | View from room

2. 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, (114 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is AED 1,213
AED 1,467 total
includes taxes & fees
24 Aug - 25 Aug
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property

3. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (101 reviews)
"Our room was very clean and comfortable - exactly what we needed to rest well. Breakfast was excellent and we felt well taken care of. We are grateful for the friendly and welcoming hosts and their staff who listened to every need and graciously provided for us. We’ll definitely return for another stay when we’re in the area."
United Kingdom
Michele
The price is AED 1,450
AED 1,701 total
includes taxes & fees
7 Sep - 8 Sep
The Inn at Stockbridge
Outdoor dining

4. Stockbridge In-town Escape

Stockbridge In-town Escape
Stockbridge
The price is AED 1,478
AED 2,334 total
includes taxes & fees
30 Aug - 31 Aug
Stockbridge In-town Escape
Superior Room, 1 King Bed, Jetted Tub | Jetted tub

5. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,010 reviews)
"First class staff and wonderful breakfast."
United States
Larry
The price is AED 585
AED 654 total
includes taxes & fees
9 Aug - 10 Aug
The Yankee Inn
Property amenity

6. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
3.5 star property
South Lee
9.2 out of 10, Wonderful, (948 reviews)
"Wonderful stay for families."
United States
Kimberly
The price is AED 459
AED 585 total
includes taxes & fees
7 Sep - 8 Sep
Holiday Inn Club Vacations Oak 'n Spruce Resort
Lobby

7. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,006 reviews)
"great location very clean friendly staff"
United States
Jeanne
The price is AED 375
AED 419 total
includes taxes & fees
31 Aug - 1 Sep
Quality Inn Lee - Lenox South
Lake view

8. Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
9.4 out of 10, Exceptional, (10 reviews)
"The air conditioning was effective and the view of the lake was peaceful and beautiful."
United States
Rita
The price is AED 599
AED 669 total
includes taxes & fees
23 Aug - 24 Aug
Berkshire Lake Lodge
Exterior

9. The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (597 reviews)
"This place was a gem. It’s small and surrounded by nature but close to restaurants, shopping, wildlife viewing areas, and historical sites. I loved that pets are free. The grounds were nice with a picnic bench and a large fire pit. If I’m in the area again, I would definitely stay here."
United States
Linda
The price is AED 413
AED 462 total
includes taxes & fees
1 Sep - 2 Sep
The Little Lion
BBQ/picnic area

10. Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
8.0 out of 10, Very Good, (31 reviews)
"Wonderful pet-friendly property in a fantastic location. Everything in the village is just a short walk away, making it easy to enjoy local shops, restaurants, and attractions."
United States
Leonardo
The price is AED 486
AED 543 total
includes taxes & fees
9 Aug - 10 Aug
Hideaway Inn Lenox
Exterior

11. 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, (798 reviews)
"very responsive staff excellent check in and check out"
United States
Kathleen
The price is AED 555
AED 620 total
includes taxes & fees
7 Sep - 8 Sep
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, cribs (free), rollaway beds (surcharge), WiFi (free)

12. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (892 reviews)
"This is my second time here. that alone is a great rating friendly owners clean room hot shower comfortable bed and alot of TV channels what more do you need? what more do you need?"
United States
John
The price is AED 314
AED 351 total
includes taxes & fees
1 Sep - 2 Sep
Monument Mountain Motel
In-room dining

13. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (683 reviews)
"Good location to towns in area"
United States
William
The price is AED 247
AED 276 total
includes taxes & fees
7 Sep - 8 Sep
Econo Lodge Lee - Great Barrington
Lake

14. 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, (1,003 reviews)
"enjoyable stay"
United States
James
The price is AED 493
AED 551 total
includes taxes & fees
7 Sep - 8 Sep
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lobby

15. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,046 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
The price is AED 393
AED 521 total
includes taxes & fees
30 Aug - 31 Aug
Berkshire Mountain Lodge
In-room safe, desk, cribs (free), rollaway beds (free)

16. Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.4 out of 10, Good, (602 reviews)
"For $200 for the night we got what you’d expect. Negatives: Nothing fancy, terrible beds and stains on the furniture in the room. We also had a dirty towel and a questionable stain on one of the bedsheets that looked like old blood. On the positive side, it was quiet, a safe area, and the staff were friendly. Fridge and microwave were in working order."
United States
jennifer
The price is AED 290
AED 324 total
includes taxes & fees
1 Sep - 2 Sep
Travelodge by Wyndham Great Barrington Berkshires
Lobby

17. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,012 reviews)
"Comfortable rooms within walking distance to Great Barrington."
United States
Lynn
The price is AED 340
AED 380 total
includes taxes & fees
1 Sep - 2 Sep
Quality Inn Great Barrington
Seasonal outdoor pool

18. Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (431 reviews)
"It was a great stay, close to many amenities. The room was clean, with a comfortable bed."
Canada
Kevin
The price is AED 349
AED 390 total
includes taxes & fees
1 Sep - 2 Sep
Sunset Inn
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, desk, laptop workspace, blackout drapes

19. 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, (1,002 reviews)
"Quite comfortable Beds"
United States
Jermaine
The price is AED 419
AED 468 total
includes taxes & fees
30 Aug - 31 Aug
Best Western Plus Berkshire Hills Inn & Suites
Lobby lounge

20. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,016 reviews)
"Clean and modern hotel close to the center part of Lenox."
United States
Ivana
The price is AED 476
AED 532 total
includes taxes & fees
7 Sep - 8 Sep
Berkshires Untold
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Stockbridge Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"We would come back here, even though there are quirky aspects to it that make it less than ideal. Overall, it's a good spot that seems like it was built in the fifties (has an old school vibe of a classic lodge), though it's only 20 years old.. What we liked: super clean, very spacious, a full kitchen, a comfortable bed, free parking, and a relatively reasonable rate. What needs improvement: We requested a quiet room and were put on the side where there is a noisy street. It was ok with earplugs. There is no housekeeping during the stay, which was fine for 3 nights, but would get old for longer. The door between the bedroom and living room needs to be fixed and didn't close fully. The toilet made a loud, running noise for 2 minutes with each flush. The handle on the fridge door broke off with normal use. We reported all of these, and none were addressed while we were there. The staff said they would send maintenance, but didn't, and didn't mention that they couldn't fix these items. Finally, we were charged a $22 resort fee that was supposed to include coffee. While they have a lovely espresso machine, no decaf was offered. As mentioned, even with the minor drawbacks, and knowing that it's more of a time share kind of place, where there's no sort of concierge service, it has many positive qualities that make it an overall good spot."
Laura 3-night trip
Posted less than an hour 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: COZY CABIN IN BERKSHIRES RESORT. - Ski resort right by Jiminy Peak Mountain Resort. 18.6 mi (30 km) from Stockbridge. Has ski-in/ski-out access, a fitness center, and beach sun loungers. 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. Enjoy the ski-in/ski-out access, fitness center, and garden. Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort - Situated just a 5-minute walk from Jiminy Peak Mountain Resort. 18.7 mi (30.1 km) from Stockbridge. Access to a fitness center, an indoor pool, and an outdoor 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.

Explore a world of travel with Expedia