Photo by William Keller

Find hotels in Stockbridge, MA from ฿2,654

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22 Dec - 23 Dec
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26 Dec - 28 Dec
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Our top choices for Stockbridge hotels

Outdoor pool, pool loungers
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1001)
"Old time charm and hot tub under the stars"
United States
Lori
The price is ฿4,711
฿6,666 total
includes taxes & fees
14 Jan - 15 Jan 2026
The Red Lion Inn
Business centre
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
The price is ฿11,995
฿14,511 total
includes taxes & fees
5 Jan - 6 Jan 2026
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, (1000)
"Very friendly and good Breakfast."
United States
Jesse
The price is ฿2,399
฿2,679 total
includes taxes & fees
4 Jan - 5 Jan 2026
Best Western Plus Berkshire Hills Inn & Suites
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (13)
"New hotel very nice"
United States
joel
The price is ฿4,240
฿4,736 total
includes taxes & fees
4 Jan - 5 Jan 2026
Element Lenox Berkshires
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, (1005)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is ฿2,376
฿2,654 total
includes taxes & fees
4 Jan - 5 Jan 2026
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, (1006)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is ฿3,150
฿3,519 total
includes taxes & fees
12 Jan - 13 Jan 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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, (997)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is ฿2,912
฿3,252 total
includes taxes & fees
24 Dec - 25 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (438)
"Nice place, easy check in"
United States
Robert
The price is ฿3,738
฿4,100 total
includes taxes & fees
5 Jan - 6 Jan 2026
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, (710)
"Great hospitality "
United States
regina maria
The price is ฿3,361
฿3,754 total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Lobby
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1002)
"The staff is always so helpful & nice, and the rooms are always clean and comfortable. This is my favorite place to stay in Lee!"
United States
Cooper
The price is ฿2,595
฿2,899 total
includes taxes & fees
11 Jan - 12 Jan 2026
Quality Inn Lee - Lenox South
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, (1000)
"Clean, pleasant staff and good breakfast. "
United States
Edward
The price is ฿3,266
฿3,649 total
includes taxes & fees
4 Jan - 5 Jan 2026
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
The price is ฿4,016
฿4,486 total
includes taxes & fees
2 Jan - 3 Jan 2026
Hilton Garden Inn Lenox Pittsfield
Egyptian cotton sheets, premium bedding, down duvets, minibar
Prospect Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (15)
"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
The price is ฿6,659
฿8,490 total
includes taxes & fees
4 Jan - 5 Jan 2026
Prospect Berkshires
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (794)
"Spacious room and loved pool and hot tub!"
United States
Deanna
The price is ฿3,100
฿4,164 total
includes taxes & fees
11 Jan - 12 Jan 2026
Berkshire Mountain Lodge
American cuisine
the Alander

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (189)
"The Alander has such a fun story, and was a great stay. We were just passing through for the night and it had everything we could need! It reminded me of Rosebud Motel group from Schitts Creek ;) if you know you know! Will definitely be staying again!"
United States
Jenna
The price is ฿3,738
฿4,186 total
includes taxes & fees
23 Dec - 24 Dec
the Alander
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
The price is ฿2,481
฿2,771 total
includes taxes & fees
23 Dec - 24 Dec
Howard Johnson by Wyndham Lenox
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cots/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, (809)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel
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
The price is ฿3,298
฿3,793 total
includes taxes & fees
23 Dec - 24 Dec
Locust Tree Bed and Breakfast LLC
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, (758)
"Clean room, very courteous staff "
United States
Thomas
The price is ฿4,240
฿4,736 total
includes taxes & fees
6 Jan - 7 Jan 2026
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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, (1001)
"My go to place for my ski weekends"
United States
Ryan
The price is ฿2,376
฿2,654 total
includes taxes & fees
5 Jan - 6 Jan 2026
Quality Inn Great Barrington
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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Stay near popular Stockbridge attractions

Norman Rockwell Museum

4.7/5 (252 reviews)
This gallery houses the world's largest collection of Norman Rockwell's iconic American illustrations. Explore his relocated studio on the scenic Berkshire estate for insight into his creative process.
See properties

National Shrine of the Divine Mercy

4.5/5 (54 reviews)
This serene sanctuary in the Berkshire Mountains is a centre for Divine Mercy devotion inspired by Saint Faustina. Visitors can join the daily 3:00 PM Chaplet or walk contemplative trails.
See properties

Learn more about Stockbridge

Norman Rockwell's Museum showcases the artist's iconic paintings of small-town American life in his former studio. Stroll down Main Street's historic district before hiking Monument Mountain for views that inspired Nathaniel Hawthorne's literary works.

See all hotels in Stockbridge
Linwood House at the Norman Rockwell Museum Stockbridge Massachusetts USA. Significant collection of the artist's original work & memorabilia on display in his hometown.
Photo by William Keller
Open Photo by William Keller

Top Stockbridge Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Yes"
Richard 3-night trip
Posted 3 days ago
The Red Lion Inn

More cheap stays in Stockbridge

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd Lenox MA
The price is ฿2,376 per night from 4 Jan to 5 Jan
฿2,376
฿2,654 total
4 Jan - 5 Jan 2026
includes taxes & fees
9/10 Wonderful! (1,000 reviews)

Frequently asked questions

Where is the best place for a stay in Stockbridge?
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood is a favourite with Expedia customers. This B&B offers free breakfast and free parking. Another top choice for your trip based on traveller reviews is The Red Lion Inn. See all available top hotels, or vacation rentals in Stockbridge.
If I need to cancel my hotel reservation in Stockbridge, will I receive a refund?
Yes, the majority of hotel reservations are refundable if you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your arrival date. If you have a reservation that's non-refundable, you might be able to cancel it and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Stockbridge.
What's the best dog-friendly hotel in Stockbridge?
The Red Lion Inn is a top hotel for people travelling with their pets, and offers 3 restaurants and an outdoor pool for its human guests. See more pet-friendly hotel accommodations in Stockbridge.
What's the best high-end place to stay in Stockbridge?
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood is a luxury B&B with a seasonal outdoor pool and a terrace, and it's a popular choice for Expedia travellers looking for an elegant place to stay. Find more luxury hotels in Stockbridge.
What's the best hotel in Stockbridge to learn about local history?
Based on our travel expertise, The Red Lion Inn is a top historic hotel bookable on our site and it features free WiFi. Also, notable landmarks to visit include Naumkeag Museum, Mission House and Berkshire Theatre Festival. See more options for historical stays in Stockbridge.
What are some accommodation options with pools in Stockbridge?
The Red Lion Inn: Features 3 restaurants, an outdoor pool and spa services. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood and Vacation Village in the Berkshires are two additional hotels that feature an on-site pool. View all hotels with pools in Stockbridge.
What is staying in Stockbridge like?
Visitors to Stockbridge will definitely enjoy the bars. Tourists can also enjoy the city's gardens, museums and architecture. In Stockbridge, there are 46 hotels and other accommodation options to choose from. Find out more about Stockbridge.
What should I do while I'm visiting Stockbridge?
Cultural venues include Norman Rockwell Museum, Mission House and Berkshire Theatre Festival. Landmarks like Naumkeag Museum, National Shrine of the Divine Mercy and Stockbridge Bowl might be worth a visit. The picturesque setting of Berkshire Botanical Garden and Housatonic River exemplify the area's natural beauty. Take a look at what more there is to see and do in Expedia's Stockbridge guide.
What's the weather like in Stockbridge?
The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Stockbridge are January, March, February and November, with each month seeing an average of 18 cm of snowfall.