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)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
United States
Gary
The price is P8,807
P12,460 total
includes taxes & fees
Mar 9 - Mar 10
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, (110 reviews)
  • cleanliness
    Experience a countryside getaway steps from Norman Rockwell Museum in Stockbridge.
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is P18,169
P21,980 total
includes taxes & fees
Feb 20 - Feb 21
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

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)
  • cleanliness
    Tranquil Berkshire hideaway near Tanglewood with complimentary amenities.
"Very friendly and good Breakfast."
United States
Jesse
The price is P5,319
P5,941 total
includes taxes & fees
Feb 9 - Feb 10
Best Western Plus Berkshire Hills Inn & Suites

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,008 reviews)
  • cleanliness
    Enjoy views of the Berkshires at this comfortable retreat with seasonal outdoor pool.
"Very friendly staff comfy beds!"
United States
Giselle
The price is P5,760
P6,434 total
includes taxes & fees
Feb 8 - Feb 9
The Yankee, Trademark Collection by Wyndham

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, (1,001 reviews)
  • cleanliness
    Serene retreat in Pittsfield with indoor pool and tranquil rooms near Tanglewood.
"Staff was very courteous and rooms clean."
United States
Steven
The price is P5,989
P6,689 total
includes taxes & fees
Mar 7 - Mar 8
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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, (1,000 reviews)
  • cleanliness
    Modern lakeside retreat with 24-hour fitness and scenic Tanglewood location.
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is P5,739
P6,410 total
includes taxes & fees
Feb 27 - Feb 28
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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, (731 reviews)
  • cleanliness
    Unwind in the Berkshires with indoor pool and free hot breakfast each morning.
"Great property, very accommodating. "
United States
Shanice
The price is P6,282
P7,017 total
includes taxes & fees
Feb 22 - Feb 23
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (445 reviews)
  • cleanliness
    Enjoy a relaxing Berkshires retreat with free breakfast and parking amenities.
"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
The price is P6,782
P7,440 total
includes taxes & fees
Feb 8 - Feb 9
Shaker Mill Inn

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1,001 reviews)
  • cleanliness
    Experience a peaceful stay near Mahaiwe Performing Arts Center.
"This was a perfect place to stay. Reasonably priced, very clean, and the young lady who worked the front desk in the evening was super friendly. We will definitely book here again. "
United States
Jerome
The price is P4,441
P4,961 total
includes taxes & fees
Mar 1 - Mar 2
Quality Inn Great Barrington

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (18 reviews)
  • cleanliness
    Relax in the Berkshires with pool access and complimentary breakfast daily.
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is P8,197
P9,156 total
includes taxes & fees
Feb 22 - Feb 23
Element Lenox Berkshires

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (850 reviews)
  • cleanliness
    Experience Berkshires charm with onsite American dining and attentive service.
"So charming, clean, thoughtful touches and a really special place!"
United States
Juliana
The price is P5,184
P5,790 total
includes taxes & fees
Mar 8 - Mar 9
Berkshires Untold

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (830 reviews)
  • cleanliness
    Convenient Lenox motel offers outdoor pool and complimentary WiFi and parking.
"Staff was very friendly and helpful."
United States
Pamela
The price is P4,051
P4,525 total
includes taxes & fees
Feb 10 - Feb 11
Howard Johnson by Wyndham Lenox

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (665 reviews)
  • cleanliness
    Perfect setting for a Berkshires visit with an indoor pool and Asian dining.
" Nice staff - beautiful hotel!"
United States
MARY
The price is P7,998
P8,933 total
includes taxes & fees
Mar 8 - Mar 9
Hilton Garden Inn Lenox Pittsfield

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (832 reviews)
  • cleanliness
    Berkshire getaway with 4 swimming pools offers seasonal outdoor retreat.
"Great overnights stay, wish I was here longer "
United States
Thomas
The price is P6,605
P8,526 total
includes taxes & fees
Feb 10 - Feb 11
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Convenient Lenox hotel with indoor pool near Tanglewood Music Center.
"The room and amenities were amazing. "
United States
Kathleen
The price is P6,998
P7,817 total
includes taxes & fees
Mar 1 - Mar 2
Hampton Inn & Suites Berkshires-Lenox

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (819 reviews)
"The room was clean, and the staff was friendly and helpful. "
United States
Damien
Monument Mountain Motel

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (828 reviews)
  • cleanliness
    Experience the beauty of the Berkshires at a cozy lodge with golf access and pool.
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is P5,794
P7,783 total
includes taxes & fees
Feb 10 - Feb 11
Berkshire Mountain Lodge

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (414 reviews)
  • cleanliness
    Experience the charming Locust Tree B&B in East Canaan with free breakfast.
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is P6,165
P7,089 total
includes taxes & fees
Feb 7 - Feb 8
Locust Tree Bed and Breakfast LLC

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,000 reviews)
  • cleanliness
    Serene Lee retreat a short drive from Tanglewood Music Center and local sights.
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is P4,941
P5,519 total
includes taxes & fees
Feb 22 - Feb 23
Quality Inn Lee - Lenox South

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (599 reviews)
  • cleanliness
    Enjoy the Berkshires with indoor pool and nearby Tanglewood Music Center.
"Our stay was great! "
United States
Gianna
The price is P7,632
P8,525 total
includes taxes & fees
Mar 1 - Mar 2
Courtyard by Marriott Lenox 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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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.

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

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 offers 3 restaurants and an outdoor pool. Other good choices for your stay in the area are Vacation Village in the Berkshires and Berkshire Mountain Lodge. 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: Features 3 restaurants, an outdoor pool, and spa services. Vacation Village in the Berkshires and Berkshire Mountain Lodge 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 44 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, Schantz Galleries, and Mission House. 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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