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

Best Resorts in Stockbridge

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Check prices for these dates

Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25
In one month
Nov 6 - Nov 8
In two months
Dec 4 - Dec 6
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, (1,005 reviews)
"Great staff, clean room and quiet."
United States
Stephan
$191 nightly
The price is $214
Nov 4 - Nov 5
Total with taxes and fees
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, (107 reviews)
"Lovely grounds, property.. room was lovely. Delicious breakfast friendly helpful owners and staff great location"
United States
Jodi
$383 nightly
The price is $428
Nov 1 - Nov 2
Total with taxes and fees
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
9.2 out of 10, Wonderful, (119 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
$376 nightly
The price is $420
Nov 1 - Nov 2
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A building with a porch and multiple windows, surrounded by purple flowers.

4. 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, (1,000 reviews)
"The facilities and property made for a wonderful family visit to the Bershires."
United States
Jared
$135 nightly
The price is $150
Oct 12 - Oct 13
Total with taxes and fees
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

5. 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)
"Beautiful setting, clean facilities. Thoroughly enjoyed my stay."
United States
Bob
$119 nightly
The price is $133
Nov 2 - Nov 3
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A reception area with a fireplace, seating, and a doormat with the logo "Quality".

6. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.6 out of 10, Excellent, (1,006 reviews)
"Very nice stay"
United States
Christine
$93 nightly
The price is $103
Nov 1 - Nov 2
Total with taxes and fees
Quality Inn Lee - Lenox South
A modern hotel lobby with seating areas, tables, and a reception desk.

7. 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, (835 reviews)
"The location is very convenient. We have been going and staying at this hotel for the past 6 years every time we come to the Berkshire area."
United States
Maria Dulce
$100 nightly
The price is $112
Nov 2 - Nov 3
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A large house with a balcony and a grassy yard.

8. The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (622 reviews)
"What a beautiful spot and the views! Pool and hot tub access is a plus!"
United States
Lidia
$115 nightly
The price is $128
Oct 18 - Oct 19
Total with taxes and fees
The Little Lion
A red building with a sign reading "Shaker Mill Inn."

9. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (476 reviews)
"Wonderful place to stay!"
United States
Mervin
$137 nightly
The price is $150
Nov 1 - Nov 2
Total with taxes and fees
Shaker Mill Inn
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

10. 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, (813 reviews)
"No extra amenities…just an average hotel"
United States
Bruce
$144 nightly
The price is $160
Nov 2 - Nov 3
Total with taxes and fees
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

11. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (662 reviews)
"Nice hotel."
United States
Tracy
$126 nightly
The price is $140
Nov 1 - Nov 2
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

12. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (920 reviews)
"Super clean and cozy and safe"
United States
Andrea
$67 nightly
The price is $74
Nov 1 - Nov 2
Total with taxes and fees
Monument Mountain Motel
A group of people performing yoga in an outdoor setting with grass and trees.

13. Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,000 reviews)
"The best aspect of this motel is the price. It is very close to the Tanglewood concert space and in West Stockbridge, a quaint town with galleries, a good bookstore, the excellent Turnpark Outdoor Sculpture Garden and "Amici" a nice Italian restaurant, etc."
United States
James
$69 nightly
The price is $76
Oct 8 - Oct 9
Total with taxes and fees
Pleasant Valley Motel West Stockbridge
A hotel room with a bed, a desk, and two wall-mounted lamps.

14. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (702 reviews)
"Have stayed here several times and it is a basic, decent place. It is in a great location, relatively clean and comfortable. Would return again."
United States
Anna
$65 nightly
The price is $73
Oct 28 - Oct 29
Total with taxes and fees
Econo Lodge Lee - Great Barrington
A snow-covered outdoor area with a patio, seating, and a covered dining area.

15. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Convenient location for Tanglewood and other Berkshire sights. Nice complimentary breakfast and arrival cocktail."
United States
Rosann
$160 nightly
The price is $179
Oct 27 - Oct 28
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

16. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,000 reviews)
"A clean, well maintained, close to everything, motel. Would highly recommend and will stay again next time we are in the area."
United States
Joan
$76 nightly
The price is $85
Nov 1 - Nov 2
Total with taxes and fees
Quality Inn Great Barrington
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

17. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,007 reviews)
"The room was spacious, clean and comfortable. I will definitely stay there again."
United States
William
$106 nightly
The price is $118
Nov 1 - Nov 2
Total with taxes and fees
The Yankee Inn
A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.

18. Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.4 out of 10, Good, (617 reviews)
"The owners and staff are very helpful. The rooms are comfortable and clean."
United States
Mark
$79 nightly
The price is $88
Oct 18 - Oct 19
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires
A large house with a covered patio area featuring outdoor seating and a fire pit.

19. The Whitlock

The Whitlock
2.0 star property
Lenox
8.4 out of 10, Very good, (392 reviews)
"The hotel staff were very friendly and helpful. There is ample parking and the location in town is great for walking to shops and restaurants. This is a very nice property."
United States
Michael
$130 nightly
The price is $145
Nov 2 - Nov 3
Total with taxes and fees
The Whitlock
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

20. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,033 reviews)
"A very good place to stay"
United States
Madhavi R
$136 nightly
The price is $152
Nov 1 - Nov 2
Total with taxes and fees
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.
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Top Stockbridge Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Very spacious and inviting..Loved the coffee maker in lobby!!!! All the girls at the front desk were extremely nice and welcoming. Very clean property and great location.. to Great Barrington, Lenox, Stockbridge, and Lee with great restaurants near by in those towns as well"
Frank 2-night trip
Posted 19 hours ago
Berkshire Mountain Lodge

Find out more about Stockbridge

Stockbridge Resorts information

Number of reviews
11,960
Accommodation
12 Resorts
Lowest Price
$73
Highest Price
$428

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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