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

Best Resorts in Stockbridge

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Aug 28 - Aug 30
In two weeks
Sep 4 - Sep 6
In one month
Sep 18 - Sep 20
In two months
Oct 16 - Oct 18
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, (1,011 reviews)
"It is a little pricey for what you get but we loved the property and the area and will be back!"
United States
Patricia
$218 nightly
The price is $243
Sep 14 - Sep 15
Total with taxes and fees
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, (116 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
$358 nightly
The price is $399
Sep 7 - Sep 8
Total with taxes and fees
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, (103 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
$396 nightly
The price is $442
Sep 13 - Sep 14
Total with taxes and fees
The Inn at Stockbridge
Outdoor dining

4. Stockbridge In-town Escape

Stockbridge In-town Escape
Stockbridge
$603 nightly
The price is $635
Aug 30 - Aug 31
Total with taxes and fees
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, (1,016 reviews)
"Very nice and convenient hotel."
United States
Karen
$158 nightly
The price is $176
Sep 14 - Sep 15
Total with taxes and fees
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, (966 reviews)
"Always a great place to stay."
United States
Claudia
$135 nightly
The price is $150
Aug 31 - Sep 1
Total with taxes and fees
Holiday Inn Club Vacations Oak 'n Spruce Resort
Lake

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,009 reviews)
"enjoyable stay"
United States
James
$128 nightly
The price is $142
Sep 14 - Sep 15
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lobby

8. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,004 reviews)
"Very nice stay"
United States
Christine
$110 nightly
The price is $122
Sep 14 - Sep 15
Total with taxes and fees
Quality Inn Lee - Lenox South
Lake view

9. Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
9.6 out of 10, Exceptional, (12 reviews)
"excellent lakeside view"
United States
mike
$141 nightly
The price is $158
Aug 31 - Sep 1
Total with taxes and fees
Berkshire Lake Lodge
Exterior

10. 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, (804 reviews)
"The room was very clean and the staff were really nice."
United States
BJORN
$115 nightly
The price is $128
Sep 20 - Sep 21
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Garden

11. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (467 reviews)
"Wonderful place to stay!"
United States
Mervin
$164 nightly
The price is $180
Sep 8 - Sep 9
Total with taxes and fees
Shaker Mill Inn
Room, 2 Queen Beds, Non Smoking

12. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (898 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
$95 nightly
The price is $106
Sep 1 - Sep 2
Total with taxes and fees
Monument Mountain Motel
Exterior

13. The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (602 reviews)
"Great location. Functional and affordable. Pet friendly."
United States
Anne
$111 nightly
The price is $124
Sep 1 - Sep 2
Total with taxes and fees
The Little Lion
Lobby

14. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,086 reviews)
"A nice place to stay in the Berkshires."
United States
Robert
$125 nightly
The price is $139
Aug 31 - Sep 1
Total with taxes and fees
Berkshire Mountain Lodge
BBQ/picnic area

15. Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
7.8 out of 10, Good, (40 reviews)
"Enjoyed the games and record players in all rooms including amazing collection of albums in main living area. Rooms are nice. Tight on parking. Great location. We would stay here again."
United States
Ann
$189 nightly
The price is $211
Aug 23 - Aug 24
Total with taxes and fees
Hideaway Inn Lenox
In-room dining

16. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (688 reviews)
"The outside of the hotel needed a lot of upkeep like paint and the stairs were particularly ugly. The inside was clean and neat and the people were wonderful. Great for a budget hotel."
United States
Lynne
$71 nightly
The price is $79
Sep 7 - Sep 8
Total with taxes and fees
Econo Lodge Lee - Great Barrington
Exterior

17. 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, (803 reviews)
"Extremely friendly and helpful staff upon arrival. Provide great insights on local restaurant opportunities, and included a five star breakfast. Highly recommend!"
United States
Lisa
$195 nightly
The price is $217
Aug 26 - Aug 27
Total with taxes and fees
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Lobby

18. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,019 reviews)
"We only stayed a night but the rooms were clean enough and the staff was extremely kind. Would stay here again."
United States
Sisile
$93 nightly
The price is $103
Sep 13 - Sep 14
Total with taxes and fees
Quality Inn Great Barrington
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area

19. East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (53 reviews)
"great place!"
United States
ERIK
$126 nightly
The price is $141
Sep 8 - Sep 9
Total with taxes and fees
East Rock Inn
Pool

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (170 reviews)
"A clean pleasant place to stay"
United States
Ken
$127 nightly
The price is $142
Sep 9 - Sep 10
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

8/10 Good
"Very nice staff and very clean big room. Not a new hotel but it is well kept and budget friendly, less than 50% of other hotels nearby, during the Tanglewood festival. Prepared food at the supermarket across the hotel was great and inexpensive. Free shuttle at the supermarket to downtown Lenox every hour."
Sirikul 1-night trip
Posted 2 hours ago
Howard Johnson by Wyndham Lenox

Find out more about Stockbridge

Stockbridge Resorts information

Number of reviews
8,364
Accommodation
12 Resorts
Lowest Price
$79
Highest Price
$442

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. 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