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Best Resorts in Stockbridge

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Next weekend
Jan 9 - Jan 11
In two weeks
Jan 16 - Jan 18
In one month
Jan 30 - Feb 1
In two months
Feb 27 - Mar 1
No exact matches found, but these alternatives could be just right

Recommended hotels in Stockbridge

Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"Old time charm and hot tub under the stars"
United States
Lori
$176 nightly
The price is $197
Jan 20 - Jan 21, 2026
Total with taxes and fees
The Red Lion Inn
Business center
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

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)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
$414 nightly
The price is $462
Jan 14 - Jan 15, 2026
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites

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, (1002)
"Very friendly and good Breakfast."
United States
Jesse
$76 nightly
The price is $85
Jan 3 - Jan 4, 2026
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1000)
"Room was very comfortable and it was clean. Staff were nice and helpful. Christmas decorations were lovely!"
United States
Clare
$88 nightly
The price is $99
Jan 3 - Jan 4, 2026
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (14)
"Rooms were very clean and spacious."
United States
Morgan
$135 nightly
The price is $151
Jan 7 - Jan 8, 2026
Total with taxes and fees
Element Lenox Berkshires
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (439)
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
United States
Carin
$105 nightly
The price is $116
Jan 6 - Jan 7, 2026
Total with taxes and fees
Shaker Mill Inn
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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, (714)
"We stay here every year and it never disappoints "
United States
Elizabeth
$98 nightly
The price is $109
Jan 25 - Jan 26, 2026
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1004)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
$101 nightly
The price is $113
Jan 8 - Jan 9, 2026
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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, (1000)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
$104 nightly
The price is $116
Jan 11 - Jan 12, 2026
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1001)
"Very comfortable beds! "
United States
Gerald
$109 nightly
The price is $122
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (659)
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
United States
Christine
$128 nightly
The price is $143
Jan 3 - Jan 4, 2026
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
Lobby
Quality Inn Great Barrington

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1000)
"My go to place for my ski weekends"
United States
Ryan
$76 nightly
The price is $85
Jan 14 - Jan 15, 2026
Total with taxes and fees
Quality Inn Great Barrington
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (799)
"Spacious room and loved pool and hot tub!"
United States
Deanna
$120 nightly
The price is $135
Jan 4 - Jan 5, 2026
Total with taxes and fees
Berkshire Mountain Lodge
Egyptian cotton sheets, premium bedding, down comforters, minibar
Prospect Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (18)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
$198 nightly
The price is $222
Jan 4 - Jan 5, 2026
Total with taxes and fees
Prospect Berkshires
Lobby
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (759)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
$135 nightly
The price is $151
Jan 19 - Jan 20, 2026
Total with taxes and fees
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Terrace/patio
Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (413)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
$105 nightly
The price is $121
Jan 1 - Jan 2, 2026
Total with taxes and fees
Locust Tree Bed and Breakfast LLC
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (71)
"Very clean and friendly staff that go above and beyond for their guests even in a snow storm! "
United States
Kira
$123 nightly
The price is $137
Jan 4 - Jan 5, 2026
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (811)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
$67 nightly
The price is $74
Jan 1 - Jan 2, 2026
Total with taxes and fees
Monument Mountain Motel
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828)
"Staff was very friendly and helpful."
United States
Pamela
$79 nightly
The price is $88
Jan 1 - Jan 2, 2026
Total with taxes and fees
Howard Johnson by Wyndham Lenox
In-room safe, desk, free cribs/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (565)
"Excellent location!!"
United States
Abdul Samad
$75 nightly
The price is $84
Jan 1 - Jan 2, 2026
Total with taxes and fees
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.
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Top Stockbridge Hotel Reviews

Prospect Berkshires

Prospect Berkshires

10/10 Excellent
"Wonderful stay - the property becomes a beautiful winter wonderland in December! Cabin was warm and well-designed, sauna was amazing and easily accessible all day, the staff was friendly, super responsive and drove us around the property when needed. Would recommend and plan to comeback!"
Michie 3-night trip
Posted 12 hours ago
Prospect Berkshires

Find out more about Stockbridge

Stockbridge Resorts information

Number of reviews
13,122
Accommodation
33 Resorts
Lowest Price
$74
Highest Price
$462

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 highest-rated resort near Stockbridge: Holiday Inn Club Vacations Oak 'n Spruce Resort - Ski resort. 2.7 mi (4.3 km) from Stockbridge. Amenities include a sauna, a fitness center, and a 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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