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
3 Apr - 5 Apr
In two weeks
10 Apr - 12 Apr
In one month
24 Apr - 26 Apr
In two months
22 May - 24 May
No exact matches found, but these alternatives could be just right

Recommended hotels in Stockbridge

Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,000 reviews)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
United States
Gary
The price is AED 493
AED 714 total
includes taxes & fees
7 Apr - 8 Apr
The Red Lion Inn
Exterior

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, (35 reviews)
"A very special, well equipped, and comfortable house with a great kitchen, bedrooms and bathrooms as well as a lovely enclosed porch and outdoor area in an amazing location. Wonderful home with all amenities and thoughtful details provided for guests. A short walk to charming town and across from a beautiful hiking area. Excellent stay!"
United States
Susan
The price is AED 1,319
AED 2,667 total
includes taxes & fees
28 Mar - 29 Mar
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
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
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is AED 1,137
AED 1,375 total
includes taxes & fees
10 Apr - 11 Apr
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (881 reviews)
"This was a great stay! The room and hotel itself were up to date and was overall a great location to check out the Berkshires. We ate one night at the hotel too and the dinner was really good! I recommend the mushroom ravioli, would stay again."
United States
Payton
The price is AED 256
AED 286 total
includes taxes & fees
30 Mar - 31 Mar
Berkshires Untold
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (24 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is AED 511
AED 570 total
includes taxes & fees
7 Apr - 8 Apr
Element Lenox Berkshires
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
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,000 reviews)
"It was a solid experience at the Best western, staff was super nice, the room was spacious and clean, the breakfast was delicious and the location is superb. Overall it was a great experience and will definitely stay there again "
United States
Kristina
The price is AED 392
AED 437 total
includes taxes & fees
29 Mar - 30 Mar
Best Western Plus Berkshire Hills Inn & Suites
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (446 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
The price is AED 368
AED 404 total
includes taxes & fees
29 Mar - 30 Mar
Shaker Mill Inn
Lake

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, (1,001 reviews)
"Room was spotless, staff was very kind!"
United States
Ilia
The price is AED 349
AED 390 total
includes taxes & fees
8 Apr - 9 Apr
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,001 reviews)
"Great visit all around. Centrally located to the skiing resorts, lots to do in town, decent breakfast spread, clean room, and for a short stay, housekeeping came when unexpected! "
United States
Amy
The price is AED 309
AED 345 total
includes taxes & fees
14 Apr - 15 Apr
Quality Inn Lee - Lenox South
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (43 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is AED 520
AED 581 total
includes taxes & fees
7 Apr - 8 Apr
Wilder House Berkshires
Double Room | Individually decorated, iron/ironing board, free WiFi

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
The price is AED 551
AED 615 total
includes taxes & fees
30 Mar - 31 Mar
The Berkshire Mountain Inn
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (835 reviews)
"Nice place and very reasonable for great location "
United States
Raymond
The price is AED 220
AED 246 total
includes taxes & fees
30 Mar - 31 Mar
Monument Mountain Motel
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (888 reviews)
"Overall pleasant stay; great facilities, staff, and location"
United States
Casey
The price is AED 318
AED 437 total
includes taxes & fees
26 Apr - 27 Apr
Berkshire Mountain Lodge
Exterior

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, (752 reviews)
"This is not my first stay. Great hotel to stay for ski trips "
United States
Michael
The price is AED 408
AED 455 total
includes taxes & fees
15 Apr - 16 Apr
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"Great place to stay and close to shops and restaurants will be back!"
United States
Marie-Pascale
The price is AED 360
AED 403 total
includes taxes & fees
29 Mar - 30 Mar
The Yankee, Trademark Collection by Wyndham
Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (295 reviews)
"Friendly staff, great location, beautiful views, cozy room."
United States
Elizabeth
The price is AED 497
AED 583 total
includes taxes & fees
4 Apr - 5 Apr
Lakehouse Inn
Exterior

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (416 reviews)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is AED 386
AED 444 total
includes taxes & fees
29 Mar - 30 Mar
Locust Tree Bed and Breakfast LLC
Lobby lounge

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"Great stay, great breakfast"
United States
Peter
The price is AED 419
AED 468 total
includes taxes & fees
9 Apr - 10 Apr
Hampton Inn & Suites Berkshires-Lenox
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1,001 reviews)
"Great location, friendly staff"
United States
James
The price is AED 247
AED 276 total
includes taxes & fees
15 Apr - 16 Apr
Quality Inn Great Barrington
In-room safe, desk, free cribs/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (574 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is AED 275
AED 308 total
includes taxes & fees
28 Mar - 29 Mar
Travelodge by Wyndham Great Barrington Berkshires
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

Berkshires Untold

Berkshires Untold

10/10 Excellent
"Berkshires Untold is an old roadside motel that has been very spiffed up. The rooms are small but clean, comfortable, and nicely decorated and updated. Our bed was comfy with high end linens and a nice updated bathroom. The major drawback to the room is the very noisy HVAC unit. There's a super cozy, attractive lounge area and a charming little restaurant and bar. The menu is small but the food is quite good and having an onsite restaurant is convenient. The price we paid for a very off season Saturday night was excellent, but the rates really jack up during the summer Tanglewood season, far beyond what one would expect for a small motel room. The staff is friendly and professional, and dogs are welcome for an $85 fee. All in all, this is a very nice and sometimes very affordable Berkshires option. "
Nancy 1-night trip
Posted 18 hours ago
Berkshires Untold

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. 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 IN AND OUT. PET FRIENDLY. - Ski resort. 18.6 mi (30 km) from Stockbridge. Enjoy the ski-in/ski-out access, fitness center, and beach sun loungers. Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more! - 9.1 mi (14.6 km) from Stockbridge. Amenities include a fitness center, an indoor pool, and an outdoor pool. 1 Bd - Vacation Village in the Berkshires - 19.2 mi (30.9 km) from Stockbridge. Access to a fitness center.
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