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

Stockbridge Hotels from S$86

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21 Aug - 22 Aug
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22 Aug - 23 Aug
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21 Aug - 23 Aug
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Our top choices for Stockbridge hotels

1. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Patricia
S$292
includes taxes & fees
14 Sept - 15 Sept
The Red Lion Inn

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
Stockbridge
United States
Philippe
S$556
includes taxes & fees
11 Sept - 12 Sept
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

3. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
United Kingdom
Michele
S$562
includes taxes & fees
15 Sept - 16 Sept
The Inn at Stockbridge

4. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
United States
Claudia
S$191
includes taxes & fees
3 Sept - 4 Sept
Holiday Inn Club Vacations Oak 'n Spruce Resort

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
James
S$181
includes taxes & fees
14 Sept - 15 Sept
The Black Swan Lee - Lenox, an Ascend Collection Hotel

6. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
Lee
United States
Christine
S$156
includes taxes & fees
14 Sept - 15 Sept
Quality Inn Lee - Lenox South

7. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
United States
BJORN
S$163
includes taxes & fees
20 Sept - 21 Sept
Holiday Inn Express Hotel & Suites Great Barrington by IHG

8. The Yankee Inn

The Yankee Inn
Lenox
United States
Karen
S$224
includes taxes & fees
14 Sept - 15 Sept
The Yankee Inn

9. Shaker Mill Inn

Shaker Mill Inn
West Stockbridge
United States
Mervin
S$233
includes taxes & fees
8 Sept - 9 Sept
Shaker Mill Inn

10. The Little Lion

The Little Lion
Great Barrington
United States
Anne
S$160
includes taxes & fees
1 Sept - 2 Sept
The Little Lion

11. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
United States
Lisa
S$276
includes taxes & fees
25 Aug - 26 Aug
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

12. Berkshires Untold

Berkshires Untold
Lenox
United States
Pamela
S$181
includes taxes & fees
9 Sept - 10 Sept
Berkshires Untold

13. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
Lee
United States
Lynne
S$101
includes taxes & fees
7 Sept - 8 Sept
Econo Lodge Lee - Great Barrington

14. The Whitlock

The Whitlock
Lenox
United States
Constance
S$240
includes taxes & fees
14 Sept - 15 Sept
The Whitlock

15. Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
Great Barrington
United States
Elspeth
S$112
includes taxes & fees
1 Sept - 2 Sept
Travelodge by Wyndham Great Barrington Berkshires

16. Quality Inn Great Barrington

Quality Inn Great Barrington
Great Barrington
United States
Sisile
S$132
includes taxes & fees
10 Sept - 11 Sept
Quality Inn Great Barrington

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
United States
Ken
S$180
includes taxes & fees
14 Sept - 15 Sept
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

18. Monument Mountain Motel

Monument Mountain Motel
Great Barrington
United States
John
S$121
includes taxes & fees
1 Sept - 2 Sept
Monument Mountain Motel

19. East Rock Inn

East Rock Inn
Great Barrington
United States
ERIK
S$179
includes taxes & fees
14 Sept - 15 Sept
East Rock Inn

20. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
United States
Nancy
S$185
includes taxes & fees
20 Sept - 21 Sept
Hampton Inn & Suites Berkshires-Lenox
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Stay near popular Stockbridge attractions

Norman Rockwell Museum

9.4/10 (347 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.
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National Shrine of the Divine Mercy

9.0/10 (83 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.
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Naumkeag Museum

9.4/10 (10 reviews)
This Gilded Age estate features a 44-room "cottage" with original Choate family furnishings. Explore the iconic Blue Steps and designed gardens while enjoying panoramic Berkshire Mountain views.
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Berkshire Botanical Garden

9.4/10 (14 reviews)
Explore 15 acres of meticulously designed "garden rooms" showcasing over 3,000 plant species native to the Berkshires. The garden's seasonal exhibitions offer an educational journey through horticulture and conservation.
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Stockbridge Bowl

This 372-acre Berkshire lake offers serene boating, fishing, and swimming against a backdrop of rolling hills. In winter, Stockbridge Bowl transforms into a magical venue for ice-skating and ice-fishing.
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Berkshire Theatre Festival

8.8/10 (3 reviews)
The historic Berkshire Theatre Festival presents classic and contemporary plays in intimate venues. Attend a summer evening performance for an immersive cultural experience in picturesque Stockbridge.
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Frelinghuysen Morris House and Studio

8.2/10 (10 reviews)
Step inside the Bauhaus-inspired home of pioneering abstract artists Morris and Frelinghuysen, surrounded by masterworks from Picasso and Lรฉger. Wander the estate's woodland trails after admiring their art collection.
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Schantz Galleries

7.2/10 (5 reviews)
This renowned gallery showcased museum-quality glass sculptures from masters like Chihuly and Tagliapietra. Though permanently closed since 2023, its legacy lives on in the contemporary glass art movement.
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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
A calm lake reflecting a forest with autumn foliage.

Top Stockbridge Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Friendly, helpful staff. Good kitchen. Great location."
Dick 2-night trip
Posted 2 hours ago
Berkshire Mountain Lodge
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

10/10 Excellent
"Loved our stay. Breakfast was amazing."
Patrick 1-night trip
Posted 13 hours ago
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good
"."
Mark 3-night trip
Posted 15 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"We come up to the Berkshires every year for Tanglewood and always stay here. The rooms are always clean and the staff friendly and helpful. The rooms have either a full kitchen or kitchenette so at the very least you can have coffee when you wake-up. The fact that Vacation Village is on Brodie Mountain it's quiet and restful."
William 3-night trip
Posted 23 hours ago
Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

10/10 Excellent
"What a wonderful stay! It was an impromptu overnight to the Berkshires and Iโ€™m so glad we chose to stay here. Our room was beautiful and clean, with a lovely view of the pond area out back from the balcony. Great bathroom and shower, very clean. Breakfast was yummy with a nice selection. The pools and hot tub were the BEST part. I absolutely will be back because one night was certainly not enough."
Kelly 1-night trip
Posted 1 day ago
The Yankee Inn
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

10/10 Excellent
"Having the pool and hot tub was great. Very clean. Breakfast was complete with oatmeal and hot breakfast choices. Location was Central to all sites like Tanglewood. Highly recommended."
Joseph 1-night trip
Posted 3 days ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
The Whitlock

The Whitlock

10/10 Excellent
"Lovely room, nice amenities."
Constance 1-night trip
Posted 4 days ago
The Whitlock
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"โ€ฆ."
Tiago 3-night trip
Posted 4 days ago
Jiminy Peak Mountain Resort

More cheap stays in Stockbridge

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
S$86
23 Aug - 24 Aug
includes taxes & fees
5.4/10 (880 reviews)
FairBridge Inn Express
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
S$112
1 Sept - 2 Sept
includes taxes & fees
7.6/10 Good! (898 reviews)
Howard Johnson by Wyndham Lenox
Quality Inn Great Barrington

Quality Inn Great Barrington

372 Main Street Great Barrington MA
S$132
10 Sept - 11 Sept
includes taxes & fees
Quality Inn Great Barrington
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St Pittsfield MA
S$162
1 Sept - 2 Sept
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
Best Western Plus Berkshire Hills Inn & Suites
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

1055 South Street Pittsfield MA
S$180
14 Sept - 15 Sept
includes taxes & fees
9.4/10 Exceptional! (169 reviews)
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
S$224
14 Sept - 15 Sept
includes taxes & fees
9.2/10 Wonderful! (1,014 reviews)
The Yankee Inn

Find out more about Stockbridge

Top reasons to visit Stockbridge

  • Charming Downtown: Explore the picturesque downtown area, rich with artistic offerings and historical allure.
  • Outdoor Adventures: Enjoy stunning hiking trails and skiing opportunities, perfect for nature enthusiasts.
  • Cultural Experiences: Attend music concerts and theatrical performances that highlight local talent.
  • Historic Sites: Visit historic houses and local libraries that showcase the area's rich heritage.
  • Varied Accommodation: Choose from intimate bed and breakfasts to comfortable hotels for a unique stay.

Find great hotels near Stockbridge

Discover the charm of Stockbridge, Massachusetts, with a variety of lodging options tailored to suit every traveller's needs. Whether you prefer the intimate atmosphere of a bed and breakfast or the comfort of a hotel, Stockbridge has something for everyone. From the historic Inn at Stockbridge to the inviting Stockbridge Country Inn, you can enjoy a unique vacation experience while exploring the area's natural beauty and adventure-filled activities.

  • Holiday Inn Club Vacations Oak nโ€™ Spruce Resort in the Berkshires by IHG: Nestled in the beautiful Berkshires, this 3.5-star resort is a family-friendly haven just 4.8km from Stockbridge. With a guest rating of 9.2 out of 10, it offers an array of adventure sports and recreational activities, making it ideal for those seeking a thrilling ski or outdoor experience. Guests can enjoy nearby skiing, snowboarding, and hiking, as well as onsite amenities such as an arcade game room, playground, and mini-golf. The resort also caters to families with childrenโ€™s services, including free cribs and a pool gate for safety.
  • The Black Swan Lee - Lenox, an Ascend Collection Hotel: This charming 3-star hotel is located 6.4km from Stockbridge and boasts a guest rating of 9.0 out of 10. The Black Swan is perfect for adventure-seekers and families, offering a pet-friendly environment. Guests can partake in onsite kayaking and nearby mountain climbing, along with activities like skiing and snowboarding. The hotel is well-equipped for families, providing free cribs and safety features like window guards. With its welcoming atmosphere, itโ€™s an excellent choice for those travelling with furry companions.
  • Holiday Inn Express Hotel & Suites Great Barrington by IHG: Situated 8.0km from Stockbridge, this budget-friendly hotel features a guest rating of 8.8 out of 10 and is well-suited for business travellers. The Holiday Inn Express offers modern amenities and comfortable accommodations, ensuring a pleasant stay while you attend to work commitments. Its strategic location provides easy access to local attractions, making it a convenient base for both business and leisure activities.

Where to stay near Stockbridge

Stockbridge, Massachusetts, offers a delightful blend of romance and culture, perfect for a captivating getaway. Stroll through the charming downtown area, where the heart of Stockbridge pulsates with artistic offerings and historical allure. Explore the scenic neighbourhoods that promise family-friendly experiences and serene landscapes. Whether you're seeking relaxation or entertainment, Stockbridge's welcoming atmosphere ensures a memorable vacation filled with enchanting moments.

  • Lenox: Nestled a mere 8.0km from Stockbridge, Lenox is a charming town known for its vibrant cultural scene. The town attracts visitors year-round, with peak arrivals during the summer months of June to August. Lenox is celebrated for its romantic and entertainment-themed experiences, offering a delightful mix of music concerts, theatre productions, and winter sports. The natural beauty surrounding Lenox, including picturesque lakes and mountains, enhances its appeal, making it an ideal destination for those seeking both leisure and adventure.
  • The Berkshires: Just 19.3km from Stockbridge, The Berkshires is a stunning region that beckons outdoor enthusiasts throughout the year. While visitor numbers peak in the summer, the area remains inviting for those seeking outdoor adventures year-round. Known for its breathtaking scenery, The Berkshires offers ample opportunities for skiing, with numerous ski fields and resorts available for thrill-seekers. Visitors can enjoy the serene lakes and majestic mountains, making it a perfect getaway for nature lovers and those looking to indulge in a bit of adventure.
  • Great Barrington: Located 11.3km from Stockbridge, Great Barrington is a lively town that thrives on its sports and adventure offerings. With a consistent influx of visitors, particularly in the summer months, Great Barrington is a hub for skiing and outdoor activities. The town features excellent ski fields and resorts, appealing to both seasoned skiers and beginners alike. Surrounded by stunning landscapes, including lakes and a national state park, Great Barrington invites travellers to explore its picturesque environment while engaging in a variety of recreational activities.

Things to do near Stockbridge

Shopping

In Stockbridge, you'll find charming shops like the Red Lion Inn Gift Shop and local artisan boutiques offering unique souvenirs. If you're up for a drive, visit the Berkshire Mall in Lanesborough, where a variety of retail options await, including well-known brands and department stores.

Recreation

The Red Lion Inn offers a relaxing atmosphere with its historic charm and spa services, perfect for unwinding. Nearby, the Norman Rockwell Museum provides artistic inspiration, while the tranquil gardens at the Berkshire Botanical Garden invite leisurely strolls amidst beautiful flora.

Adventure

Lime Rock Park, located 40.2km from Stockbridge, offers exhilarating motor racing experiences amidst a lively atmosphere. For a thrilling adventure, visit Catamount Aerial Adventure Park, situated 17.7km away, where you can navigate zip lines and ropes courses while soaking in the beauty of the great outdoors.

Nightlife

For a relaxed evening, visit the Red Lion Inn's tavern to enjoy a selection of local wines and classic cocktails. Alternatively, the Berkshire Theatre Group often hosts performances that provide a vibrant cultural experience, showcasing talented artists in an intimate setting.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Stockbridge

Stockbridge, Massachusetts, is an ideal destination for romantic getaways and cultural experiences. Visitors can explore historic houses, nature reserves, and local libraries, all of which provide a blend of outdoor activities and family-friendly experiences. Whether you're seeking culture or simply wish to enjoy the serene surroundings, Stockbridge has something for everyone. Don't forget to visit the charming town itself for a taste of its unique charm and attractions.

  • Norman Rockwell Museum: Immerse yourself in the charming world of American illustration at the Norman Rockwell Museum. Located in Stockbridge, this museum showcases an extensive collection of Rockwell's iconic artworks, reflecting the culture and spirit of 20th-century America.
  • National Shrine of the Divine Mercy: This serene shrine, situated within Stockbridge, offers a peaceful retreat for reflection and prayer, dedicated to the message of Divine Mercy. Its beautiful grounds and sacred atmosphere provide a unique spiritual experience.
  • The Mount: Just 6.4km from Stockbridge, The Mount is the historic home of author Edith Wharton. Explore the stunning gardens and architecture that inspired her literary works, all set against the backdrop of the picturesque Berkshires.

Best time to go to Stockbridge

The best time to visit Stockbridge is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January22.8ยฐF (-5.1ยฐC)Light RainMostly CloudySlightly LowAverage
February24.6ยฐF (-4.1ยฐC)Light RainMostly CloudySlightly LowAverage
March32.5ยฐF (0.3ยฐC)Light RainMostly CloudySlightly LowSlightly Low
April44.2ยฐF (6.8ยฐC)Light RainMostly CloudyAverageSlightly Low
May56.3ยฐF (13.5ยฐC)Light RainMostly SunnyAverageAverage
June64.0ยฐF (17.8ยฐC)Light RainMostly SunnyAverageAverage
July70.3ยฐF (21.3ยฐC)Light RainMostly SunnySlightly HighSlightly High
August68.4ยฐF (20.2ยฐC)Light RainMostly SunnySlightly HighSlightly High
September61.3ยฐF (16.3ยฐC)Light RainMostly SunnySlightly HighAverage
October50.0ยฐF (10.0ยฐC)Light RainMostly SunnyAverageSlightly High
November37.8ยฐF (3.2ยฐC)Light RainMostly SunnyAverageSlightly Low
December29.5ยฐF (-1.4ยฐC)Light RainMostly CloudyAverageAverage

The nearest major airports for your trip to Stockbridge

To reach Stockbridge, Massachusetts, you have several airport options. Hartford, CT (BDL-Bradley Intl.) is 66.0km away, with nearby hotels such as the 4-star DoubleTree by Hilton Hartford - Bradley Airport, located 1.6km from the airport. Albany, NY (ALB-Albany Intl.) is 64.4km from Stockbridge, offering accommodations like The Landing Hotel at Rivers Casino & Resort, 12.9km from the airport. Finally, White Plains, NY (HPN-Westchester County) is 140.0km away, with the 5-star Opus Westchester, located 6.4km from the airport. Each hotel provides convenient transport services to their respective airports, ensuring a smooth journey for your visit.

Frequently asked questions

Where is the best place for a stay in Stockbridge?
The Red Lion Inn is one of the top choices for your stay based on our traveller data. This hotel offers 3 restaurants and an outdoor pool. Other good choices for your trip include The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood and The Inn at Stockbridge. 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. The Inn at Stockbridge is another good option for you and your pet. 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, Berkshire Theatre Festival and Mission House.
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 The Inn at Stockbridge 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 55 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, Schantz Galleries 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 19ยฐC, while the coldest months are January and February, with an average of -3ยฐC. The snowiest months in Stockbridge are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

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