Best Resorts in Stockbridge

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Check prices for these dates

Next weekend
May 29 - May 31
In two weeks
Jun 5 - Jun 7
In one month
Jun 19 - Jun 21
In two months
Jul 17 - Jul 19
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, (1,001 reviews)
"a delightful inn centrally located in charming Stockbridge"
United States
molly
$187 nightly
The price is $209
May 31 - Jun 1
Total with taxes and fees
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, (38 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
$766 nightly
The price is $856
May 25 - May 26
Total with taxes and fees
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, (111 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
$358 nightly
The price is $399
Jun 7 - Jun 8
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Superior Room, 1 King Bed, Jetted Tub | Jetted tub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"Breakfast ok, coffee good, staff great"
United States
Peter
$106 nightly
The price is $119
May 28 - May 29
Total with taxes and fees
The Yankee Inn
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (457 reviews)
"Wonderful place to stay!"
United States
Mervin
$98 nightly
The price is $108
May 25 - May 26
Total with taxes and fees
Shaker Mill Inn
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (946 reviews)
"Clean and great job staffing "
United States
Pedro
$111 nightly
The price is $124
May 25 - May 26
Total with taxes and fees
Berkshire Mountain Lodge
BBQ/picnic area

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
8.0 out of 10, Very Good, (2 reviews)
"After a little snafu with check-in (we had completed the form in advance and never received the room number text), we were able to get checked in with the virtual front desk. The inn was clean and well appointed and centrally located. The common areas felt inviting and useful for both the adults and kids. We would stay again."
United States
Samantha
$132 nightly
The price is $147
May 25 - May 26
Total with taxes and fees
Hideaway Inn Lenox
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, (1,001 reviews)
"Room was clean. Breakfast was fresh and the area was pristine. All staff was pleasant. "
United States
Melinda
$108 nightly
The price is $121
May 26 - May 27
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (955 reviews)
"Great stay!"
United States
Aditya
$116 nightly
The price is $129
May 25 - May 26
Total with taxes and fees
Berkshires Untold
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (96 reviews)
"This is a great hotel-super clean, nice breakfast, staff very pleasant and helpful. Close to Pittsfield but quieter. Pool and hot tub were great. Highly recommend staying here if you’re in the area."
United States
Kathleen
$127 nightly
The price is $142
May 28 - May 29
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Lake

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,005 reviews)
"Clean rooms and lovely view"
Canada
Laraib
$116 nightly
The price is $130
Jun 1 - Jun 2
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,002 reviews)
"Great staff breakfast was good location was close enough to walk but far enough from the noise "
United States
Braynd
$83 nightly
The price is $93
May 26 - May 27
Total with taxes and fees
Quality Inn Great Barrington
Lobby lounge

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
$182 nightly
The price is $203
May 31 - Jun 1
Total with taxes and fees
Element by Marriott Lenox Berkshires
Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,362 reviews)
"great stay. "
United States
John
$108 nightly
The price is $120
May 25 - May 26
Total with taxes and fees
Vacation Village in the Berkshires
Courtyard

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (97 reviews)
"We enjoyed our stay. Staff was nice and the motel is set between several different towns to explore. We plan to stay again soon!"
United States
Shakeila
$99 nightly
The price is $108
May 25 - May 26
Total with taxes and fees
The Springs Motel
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (181 reviews)
"Breakfast was great"
United States
Archna
$143 nightly
The price is $164
May 25 - May 26
Total with taxes and fees
Blackberry River 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, (856 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
$76 nightly
The price is $85
May 25 - May 26
Total with taxes and fees
Monument Mountain Motel
Breakfast, lunch and dinner served

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (678 reviews)
"Clean room, staff was friendly and efficient. Great breakfast"
United States
Donna
$144 nightly
The price is $160
May 31 - Jun 1
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (856 reviews)
"Clean comfortable room. Very nice staff. Close to everything in downtown Pittsfield. This is the only place I stay when I’m in Pittsfield. Very peaceful. Excellent place to relax. "
United States
Jennifer
$73 nightly
The price is $81
May 25 - May 26
Total with taxes and fees
Berkshire Inn
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, (766 reviews)
"Above average hotel breakfast. Very clean hotel."
United States
Helen
$124 nightly
The price is $139
Jun 1 - Jun 2
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington 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.
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Top Stockbridge Hotel Reviews

The Whitlock

The Whitlock

8/10 Good
"A beautiful old inn in the heart of a lovely old town."
Linda 2-night trip
Posted 14 hours ago
The Whitlock

Find out more about Stockbridge

Stockbridge Resorts information

Number of reviews
12,470
Accommodation
29 Resorts
Lowest Price
$81
Highest Price
$856

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 resort near Stockbridge: Holiday Inn Club Vacations Oak 'n Spruce Resort - Ski resort. 2.7 mi (4.3 km) from Stockbridge. Enjoy the sauna, fitness center, and terrace.
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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