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

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Check prices for these dates

Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11
In one month
Oct 23 - Oct 25
In two months
Nov 20 - Nov 22
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, (1,003 reviews)
"this grand old hotel is warm and welcoming — a real hub of Bershires life and history"
United States
James
The price is CA $217
CA $312 total
includes taxes & fees
Sep 30 - Oct 1
The Red Lion Inn

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
The price is CA $596
CA $698 total
includes taxes & fees
Sep 23 - Sep 24
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, (118 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is CA $725
CA $877 total
includes taxes & fees
Oct 12 - Oct 13
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, (40 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 traveller
The price is CA $646
CA $1,201 total
includes taxes & fees
Sep 28 - Sep 29
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

5. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,004 reviews)
"The room was spacious, clean and comfortable. I will definitely stay there again."
United States
William
The price is CA $148
CA $165 total
includes taxes & fees
Sep 28 - Sep 29
The Yankee Inn
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

6. 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, (1,006 reviews)
"A very clean and lovely property!"
United States
Ann M
The price is CA $179
CA $200 total
includes taxes & fees
Sep 29 - Sep 30
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A building with a porch and multiple windows, surrounded by purple flowers.

7. 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, (990 reviews)
"Perfect stay"
United States
Linda
The price is CA $164
CA $211 total
includes taxes & fees
Sep 27 - Sep 28
Holiday Inn Club Vacations Oak 'n Spruce Resort
A reception area with a fireplace, seating, and a doormat with the logo "Quality".

8. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.6 out of 10, Excellent, (1,004 reviews)
"Great location for a trip to Tanglewood! Clean room, decent bedding, free breakfast, workout room, close to good restaurants. Would stay again"
United States
Wendy
The price is CA $154
CA $172 total
includes taxes & fees
Oct 19 - Oct 20
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.

9. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (915 reviews)
"Great place. Staff, property , parking, location"
United States
Victor
The price is CA $108
CA $120 total
includes taxes & fees
Oct 18 - Oct 19
Monument Mountain Motel
A large house with a balcony and a grassy yard.

10. The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (612 reviews)
"Great location. Functional and affordable. Pet friendly."
United States
Anne
The price is CA $145
CA $162 total
includes taxes & fees
Oct 22 - Oct 23
The Little Lion
A modern hotel lobby with seating areas, tables, and a reception desk.

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, (827 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
The price is CA $187
CA $208 total
includes taxes & fees
Oct 19 - Oct 20
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A red building with a sign reading "Shaker Mill Inn."

12. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (474 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is CA $245
CA $269 total
includes taxes & fees
Sep 23 - Sep 24
Shaker Mill Inn
A large house with a covered patio area featuring outdoor seating and a fire pit.

13. The Whitlock

The Whitlock
2.0 star property
Lenox
8.4 out of 10, Very good, (385 reviews)
"Cute inn right in the center of it all. Easy check in and check out."
United States
Maeve
The price is CA $194
CA $217 total
includes taxes & fees
Sep 23 - Sep 24
The Whitlock
A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.

14. Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.4 out of 10, Good, (616 reviews)
"Front desk was very pleasant. Room was awful!"
United States
Kevin
The price is CA $105
CA $117 total
includes taxes & fees
Sep 23 - Sep 24
Travelodge by Wyndham Great Barrington Berkshires
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
The price is CA $230
CA $264 total
includes taxes & fees
Sep 23 - Sep 24
The Cornell Inn, Lenox & The Berkshires
A round wooden table with two wine glasses and a green bottle, set against a window with a view of a blue railing and trees.

16. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (699 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
The price is CA $97
CA $109 total
includes taxes & fees
Sep 29 - Sep 30
Econo Lodge Lee - Great Barrington
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

17. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,150 reviews)
"Clean & comfortable stay"
United States
Robert
The price is CA $110
CA $155 total
includes taxes & fees
Oct 1 - Oct 2
Berkshire Mountain Lodge
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

18. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,011 reviews)
"It was perfect for our weekend away, clean, comfortable bed and a decent breakfast, definitely worth the value:)"
United States
Kimberly
The price is CA $141
CA $158 total
includes taxes & fees
Oct 22 - Oct 23
Quality Inn Great Barrington
A calm lake at dusk with a wooden dock and two chairs facing the water.

19. Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
9.6 out of 10, Exceptional, (19 reviews)
"excellent lakeside view"
United States
mike
The price is CA $190
CA $212 total
includes taxes & fees
Sep 28 - Sep 29
Berkshire Lake Lodge
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, (1,022 reviews)
"It"s a very nice small Hotel- nicely appointed"
United States
Drue
The price is CA $196
CA $219 total
includes taxes & fees
Sep 28 - Sep 29
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"I am disappointed that it has been over two weeks and I have yet to receive my room deposit back. They told me 7-10 days"
Graham 2-night trip
Posted 1 hour ago
Vacation Village in the Berkshires

Find out more about Stockbridge

Stockbridge Resorts information

Number of reviews
9,580
Accommodation
12 Resorts
Lowest Price
CA $109
Highest Price
CA $1,201

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.
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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