Stockbridge Hotels

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Our top choices for Stockbridge hotels

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,001 reviews)
"Breakfast was awesome, I recommend the Cinnamon French Toast."
United States
Walter
The price is P8,308
P11,994 total
includes taxes & fees
Apr 30 - May 1
The Red Lion Inn

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
The price is P18,795
P22,737 total
includes taxes & fees
May 10 - May 11
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (916 reviews)
"Such a cool and affordable place to stay in the Berkshires. Great lobby/bar with a good restaurant."
United States
Kathy
The price is P5,029
P5,617 total
includes taxes & fees
May 5 - May 6
Berkshires Untold

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (447 reviews)
"Everything was great— the cleanliness, the plentiful breakfast, the character and coziness, and the proximity to Amici across the street (free dessert with your room key)."
United States
Patrick
The price is P6,620
P7,262 total
includes taxes & fees
May 5 - May 6
Shaker Mill Inn

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
The price is P6,175
P6,898 total
includes taxes & fees
Apr 29 - Apr 30
Best Western Plus Berkshire Hills Inn & Suites

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is P10,789
P12,052 total
includes taxes & fees
May 10 - May 11
Element Lenox Berkshires

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1,001 reviews)
"Very friendly staff and conviently located"
United States
Dawn
The price is P4,558
P5,091 total
includes taxes & fees
Apr 29 - Apr 30
Quality Inn Great Barrington

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Great place to stay and close to shops and restaurants will be back!"
United States
Marie-Pascale
The price is P6,280
P7,014 total
includes taxes & fees
May 11 - May 12
The Yankee Inn

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, (1,001 reviews)
"Beautiful place- beautiful views "
United States
Yanis
The price is P6,948
P7,761 total
includes taxes & fees
May 3 - May 4
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (845 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
The price is P3,635
P4,060 total
includes taxes & fees
Apr 30 - May 1
Monument Mountain Motel

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (916 reviews)
"Spacious, clean, and the pool was warm and perfect for family swimming "
United States
Danielle
The price is P5,261
P7,233 total
includes taxes & fees
May 25 - May 26
Berkshire Mountain Lodge

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, (758 reviews)
"Nice clean room, clean and well maintained breakfast was tasteful each day. Desk Clerk very helpful in giving out direction, Breaksfast person, very friendly. Hotel is centrally located, shop and restaurant nearby"
United States
Berdest
The price is P6,741
P7,530 total
includes taxes & fees
May 4 - May 5
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (45 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is P9,773
P10,917 total
includes taxes & fees
Apr 28 - Apr 29
Wilder House Berkshires

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (417 reviews)
"Clean, good breakfast, friendly staff"
United States
Debra
The price is P6,377
P7,334 total
includes taxes & fees
Apr 28 - Apr 29
Locust Tree Bed and Breakfast LLC

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Good location and great breakfast."
United States
Linda
The price is P7,640
P8,534 total
includes taxes & fees
May 17 - May 18
Hampton Inn & Suites Berkshires-Lenox

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (576 reviews)
"Clean"
United States
Brian
The price is P4,555
P5,088 total
includes taxes & fees
Apr 28 - Apr 29
Travelodge by Wyndham Great Barrington Berkshires

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,001 reviews)
"Great location "
United States
Edith
The price is P6,249
P6,980 total
includes taxes & fees
May 19 - May 20
Quality Inn Lee - Lenox South

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (95 reviews)
"Great quaint place. Great staff and very clean. "
United States
Janelle
The price is P6,388
P7,008 total
includes taxes & fees
Apr 28 - Apr 29
The Springs Motel

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"Delicious breakfast and beautiful room!"
United States
Laarni
The price is P8,094
P9,313 total
includes taxes & fees
May 5 - May 6
The Cornell Inn, Lenox & The Berkshires

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
9.8 out of 10, Exceptional, (6 reviews)
"The new owners have done a great job. The place is immaculate, the room was very comfortable and well appointed, the common areas charming. Highly recommended."
United States
Robert
The price is P10,476
P11,702 total
includes taxes & fees
Apr 28 - Apr 29
The Berkshire Mountain Inn
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

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.

Vivid autumn foliage reflected in a calm lake surrounded by a dense forest under a clear blue sky in Stockbridge, Massachusetts

Top Stockbridge Hotel Reviews

More cheap stays in Stockbridge

Find out more about Stockbridge

Top reasons to visit Stockbridge

  • Charming Atmosphere: Stroll through picturesque landscapes and experience the warm New England hospitality in the delightful town of Stockbridge.
  • Cultural Exploration: Discover historic houses and museums that reflect the rich heritage of the region.
  • Outdoor Activities: Enjoy a range of family-friendly outdoor pursuits, including scenic walks around the serene Stockbridge Bowl.
  • Vibrant Entertainment: Attend music concerts, theatre performances, and enjoy the lively nightlife.
  • Winter Sports: Take advantage of nearby ski resorts for thrilling winter adventures.

Find great hotels near Stockbridge

Explore the charming town of Stockbridge, Massachusetts, where a delightful array of accommodation options awaits. From inviting bed and breakfasts to well-appointed hotels, you'll find the ideal lodging for your adventure-filled family getaway. Whether you seek a pet-friendly retreat or a cosy inn for a warm, welcoming experience, Stockbridge has something for everyone. Discover the best hotels and inns to make your stay truly memorable in this picturesque New England destination.

  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: This 3.5-star resort combines family-friendly amenities with a welcoming environment for LGBTQIA travellers. Located 4.8km from Stockbridge, it offers a delightful mix of leisure and recreation for all ages. Families can enjoy the onsite arcade game room, mini-golf, and a shared playground, ensuring an entertaining stay for children. The resort also provides free cribs and is affiliated with LGBTQI travel guides, making it a perfect choice for inclusive family vacations. With its quaint natural surroundings and diverse facilities, it promises a memorable experience for everyone.
  • The Black Swan Lee - Lenox, an Ascend Collection Hotel: Situated 6.4km from Stockbridge, this 3-star hotel is ideal for families and adventure enthusiasts alike. The Black Swan offers a range of exciting activities, including kayaking, fishing, and nearby skiing, making it perfect for those seeking outdoor adventures. Pet-friendly policies ensure that furry companions are welcome, with specific amenities available for them. Additionally, the hotel features child-friendly services such as window guards and complimentary cribs, catering to families looking for a fun-filled getaway in a beautiful setting.
  • Holiday Inn Express Hotel & Suites Great Barrington by IHG: Located 8.0km from Stockbridge, this hotel is an excellent choice for business travellers and LGBTQIA visitors seeking comfort and convenience. With its modern amenities and a focus on guest satisfaction, it offers a relaxed atmosphere ideal for both work and leisure. The property's affiliation with LGBTQI travel guides ensures an inclusive experience, while its strategic location near local attractions makes it a practical option for exploring the Berkshires. Guests appreciate the friendly service and well-appointed rooms, making it a suitable choice for any stay.

Where to stay near Stockbridge

Stockbridge offers a delightful blend of romance and culture, perfect for a memorable holiday. Explore the charming streets and experience New England hospitality, with nearby Lenox providing stunning scenery and classic destinations. Whether you seek relaxation or family-friendly activities, the area is adorned with beautiful spots that cater to all tastes. From historical landmarks to serene landscapes, Stockbridge promises an enchanting escape for every traveller.

  • Lenox: Nestled a mere 8.0km from Stockbridge, Lenox is a charming town that comes alive with a romantic and cultural atmosphere. Visitors flock here for its entertainment-themed experiences, particularly during the summer months of June to August when the local theatre and music concerts are in full swing. The scenic beauty of the nearby mountains and lakes provides a stunning backdrop, while places of worship add a sense of tranquillity. Whether you're enjoying a summer concert or hitting the slopes in winter, Lenox offers a delightful mix of recreational activities for every season.
  • The Berkshires: Located approximately 19.3km from Stockbridge, The Berkshires is a haven for outdoor enthusiasts and adventure seekers. With a relatively steady influx of visitors, peaking during the warmer months, this region is perfect for those who appreciate breathtaking scenery. The Berkshires is renowned for its ski resorts and fields, making it an ideal destination for winter sports. Besides skiing, the area is dotted with beautiful lakes and majestic mountains, providing endless opportunities for hiking, biking, and enjoying nature’s splendour.
  • Pittsfield: Also situated 19.3km from Stockbridge, Pittsfield is a vibrant city that draws adventurers and outdoor lovers throughout the year. With peak visitor numbers from June to August, this area offers a plethora of activities, including skiing and exploring the nearby ski fields and resorts. The city is enriched with natural landmarks like lakes and mountains, alongside historical monuments that tell the story of the region. Whether you're seeking thrills on the slopes or a leisurely day out, Pittsfield promises a fulfilling experience for all.

Things to do in and around Stockbridge

Stockbridge offers a delightful blend of romance and culture, perfect for a memorable getaway. Visitors can explore local attractions such as music concerts and theatre performances, while winter sports enthusiasts will appreciate the nearby ski resorts. The vibrant nightlife and the scenic Stockbridge Golf Club add to the area's charm, making it an excellent destination for entertainment and leisure activities.

Shopping

In Stockbridge, visit the Berkshire Mountain Country Store, Hoffman's Pottery, and Charles H. Baldwin & Sons, all within 6.4km, offering unique gifts and souvenirs. If you're up for a drive, explore more shops in nearby towns for additional local treasures.

Recreation

Experience the Tanglewood Music Center’s enchanting concerts, set in a vibrant atmosphere perfect for relaxation. Enjoy a round of golf at Wyndhurst Golf & Club, surrounded by beautiful landscapes, or unwind at Lake Mansfield Park, where you can immerse yourself in nature and rejuvenate your spirit.

Adventure

Ski Butternut offers exhilarating skiing experiences within a scenic mountain setting, perfect for winter sports enthusiasts. For outdoor adventurers, the Housatonic River Walk provides picturesque hiking trails alongside the river, showcasing stunning scenery. Catamount Aerial Adventure Park features thrilling zipline courses, promising an adrenaline-fueled day among the treetops.

Nightlife

In Stockbridge, Shakespeare and Company offers an enchanting theatre experience just 8.0km away, while the Berkshire Theatre Festival provides captivating performances within the town. For a slightly longer journey, the Mahaiwe Performing Arts Center, located 11.3km away, promises delightful cultural entertainment, all set against a romantic backdrop.

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

Booking tips and Expedia advantages for Stockbridge

To save money on your trip to Stockbridge, consider visiting during the cheaper months of March to April and November, with Tuesdays being the least expensive days to stay. Utilise Expedia to find great deals by filtering for your budget and combining hotel bookings with flights for additional savings. Look for flexible booking options and upfront pricing to avoid unexpected costs. Free activities such as exploring the picturesque town and nearby parks can also enhance your experience without straining your budget.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Stockbridge are March to April and November, where the prices are slightly lower. This is in comparison to July to August and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Stockbridge is Tuesday. The most expensive day to stay in Stockbridge is Saturday.
  • Find cheap hotels on Expedia: Utilise Expedia’s search tool to refine your preferences, such as your budget, desired location, and the type of accommodation you favour. To discover the most affordable prices and offers, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can make significant savings by combining your Stockbridge hotel reservation with your flights and activities through an Expedia package.

Find the best attractions in and around Stockbridge

Stockbridge is an idyllic destination for romantic getaways and cultural exploration, featuring historic houses, scenic reserves, and the serene Stockbridge Bowl. Visitors can delve into local culture at museums and enjoy outdoor activities that cater to families. The charming atmosphere invites leisurely strolls through picturesque landscapes, making it a perfect blend of relaxation and entertainment for all types of travellers.

  • Great Barrington Historical Society & Museum: Located 12.9km from Stockbridge, this museum offers a deep dive into the rich history of the region. Visitors will appreciate the cultural vibes as they explore various exhibits that highlight local heritage and significant events.
  • National Shrine of the Divine Mercy: Situated within Stockbridge, this serene shrine is a place of reflection and peace. The beautiful grounds and architecture create a culturally enriching atmosphere, perfect for contemplation and spiritual connection.
  • Norman Rockwell Museum: Also located in Stockbridge, this art museum is dedicated to the beloved American artist Norman Rockwell. Guests can enjoy a remarkable collection of his works, along with insights into his creative process, all within a culturally vibrant setting.

Best time to go to Stockbridge

The best time to visit Stockbridge can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Stockbridge falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Stockbridge falls in January, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January22.8°F (-5.1°C)Light RainMostly CloudySlightly LowAverage
February24.6°F (-4.1°C)Light RainMostly CloudySlightly LowAverage
March32.5°F (0.3°C)Light RainMostly CloudySlightly LowSlightly Low
April44.2°F (6.8°C)Light RainMostly CloudyAverageSlightly Low
May56.3°F (13.5°C)Light RainMostly SunnyAverageAverage
June64.0°F (17.8°C)Light RainMostly SunnyAverageAverage
July70.3°F (21.3°C)Light RainMostly SunnySlightly HighSlightly High
August68.4°F (20.2°C)Light RainMostly SunnySlightly HighSlightly High
September61.3°F (16.3°C)Light RainMostly SunnySlightly HighAverage
October50.0°F (10.0°C)Light RainMostly SunnyAverageSlightly High
November37.8°F (3.2°C)Light RainMostly SunnyAverageSlightly Low
December29.5°F (-1.4°C)Light RainMostly CloudyAverageAverage

The nearest major airports for your trip to Stockbridge

Visiting Stockbridge, Massachusetts, is convenient with several major airports nearby. Hartford, CT (BDL-Bradley Intl.) is 66.0km away, with excellent hotel options like the 4-star Simsbury 1820 House, 11.3km from the airport, and the Marriott Hartford Downtown, 19.3km away. Albany, NY (ALB-Albany Intl.) is 64.4km distant, featuring hotels like the 4-star Landing Hotel at Rivers Casino & Resort, 12.9km from the airport, and the Crowne Plaza Albany, just 1.6km away. For those closer, Pittsfield, MA (PSF-Pittsfield Municipal) is a mere 16.1km away, with notable accommodations such as the Central Downtown Inn & Suites, 3.2km from the airport, and the Red Lion Inn, 16.1km away.

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 traveler data. This hotel is a short 15-minute walk from National Shrine of the Divine Mercy, and it offers 3 restaurants and an outdoor pool. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood is another good choice for your trip. 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! You'll find that most hotel room reservations are fully refundable as long as you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before check in. If you have a non-refundable reservation, you might be able to cancel it and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Stockbridge.
What's the best pet-friendly accommodation in Stockbridge?
The Red Lion Inn is a top hotel for people traveling 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 travelers looking for an elegant place to stay. Find more luxury hotels in Stockbridge.
What's the best accommodation in Stockbridge to absorb the 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.
What are some hotels with pools in Stockbridge?
The Red Lion Inn: Hotel, 15-minute walk from National Shrine of the Divine Mercy. 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 offer an onsite pool. View all hotels with pools in Stockbridge.
What is staying in Stockbridge like?
Visitors to Stockbridge are sure to enjoy the bars. Tourists can also enjoy the city's gardens, museums, and architecture. In Stockbridge, there are 48 hotels and other accommodations to choose from. Find out more about Stockbridge.
What should I see while I'm in 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. Check out what more 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 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.

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