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, (1,007 reviews)
"a delightful inn centrally located in charming Stockbridge"
United States
molly
The price is €199
includes taxes & fees
4 Jun - 5 Jun
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 €319
includes taxes & fees
26 May - 27 May
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,005 reviews)
"Great place to stay and close to shops and restaurants will be back!"
United States
Marie-Pascale
The price is €94
includes taxes & fees
13 May - 14 May
The Yankee 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 €104
includes taxes & fees
12 May - 13 May
Best Western Plus Berkshire Hills Inn & Suites

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (932 reviews)
"Great stay!"
United States
Aditya
The price is €108
includes taxes & fees
14 May - 15 May
Berkshires Untold

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (453 reviews)
"Everything was excellent"
United States
Barbara
The price is €102
includes taxes & fees
10 May - 11 May
Shaker Mill Inn

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 €158
includes taxes & fees
20 May - 21 May
Element Lenox Berkshires

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (925 reviews)
"Spacious, clean, and the pool was warm and perfect for family swimming "
United States
Danielle
The price is €102
includes taxes & fees
24 May - 25 May
Berkshire Mountain Lodge

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (849 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
The price is €65
includes taxes & fees
17 May - 18 May
Monument Mountain Motel

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, (1,005 reviews)
"Staff was friendly, room was clean and the beds were comfortable. Dog friendly also. Good breakfast selection. I would stay there again."
United States
Lillian
The price is €119
includes taxes & fees
31 May - 1 Jun
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very good, (1,008 reviews)
"Very friendly staff and conviently located"
United States
Dawn
The price is €80
includes taxes & fees
13 May - 14 May
Quality Inn Great Barrington

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (177 reviews)
"Great staff. "
United States
wesley
The price is €152
includes taxes & fees
10 May - 11 May
Blackberry River Inn

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (96 reviews)
"We enjoyed our stay. Staff was nice and the motel is set between several different towns to explore. We plan to stay again soon!"
United States
Shakeila
The price is €101
includes taxes & fees
10 May - 11 May
The Springs Motel

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (46 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is €183
includes taxes & fees
12 May - 13 May
Wilder House Berkshires

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,351 reviews)
"great stay. "
United States
John
The price is €91
includes taxes & fees
12 May - 13 May
Vacation Village in the 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 €102
includes taxes & fees
10 May - 11 May
Locust Tree Bed and Breakfast LLC

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 €180
includes taxes & fees
13 May - 14 May
The Berkshire Mountain Inn

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, (92 reviews)
"Room was clean, bed was comfortable, pool was nice, breakfast and coffee were good!"
United States
Haley
The price is €112
includes taxes & fees
17 May - 18 May
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (559 reviews)
"A nice safe and quiet place to stay. Park right in front of your door. My dog loved the large grass area. The room was large and the beds very comfortable. The heat was on when we arrived which was great . It was cold and snowy that day. I loved having the self check-in and check out. We plan on going back the next time we are in the area. "
United States
SUSAN
The price is €104
includes taxes & fees
11 May - 12 May
The Little Lion

The Whitlock

The Whitlock
2.0 star property
Lenox
8.6 out of 10, Excellent, (295 reviews)
"Lovely historical hotel within walking distance to many great shops and restaurants. Staff members maintained good communication and were very helpful throughout our stay. Rooms were clean, quiet, and comfortable. Would definitely stay there again."
United States
Elaine
The price is €109
includes taxes & fees
12 May - 13 May
The Whitlock
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

  • Cultural Hub: Stockbridge is rich in culture, offering captivating music concerts and engaging theatre performances for visitors to enjoy.
  • Romantic Getaway: The charming town is perfect for couples, featuring picturesque surroundings and delightful accommodations.
  • Outdoor Adventures: Visitors can indulge in thrilling activities such as skiing and explore scenic lakes and nature reserves.
  • Historical Sites: Discover the town's architectural beauty and rich history through its historic houses and landmarks.
  • Charming Accommodations: A range of delightful lodging options, from bed & breakfasts to hotels, cater to all travellers.

Find great hotels near Stockbridge

Discover a range of delightful accommodation options in Stockbridge, Massachusetts, ideal for every traveller. From charming bed & breakfasts to well-appointed hotels, you'll find the perfect retreat for a family getaway, an adventure-filled holiday, or a pet-friendly escape. Explore nearby options in Great Barrington and Lee, ensuring a memorable stay in this picturesque region.

  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Embrace a vibrant family-friendly atmosphere at this 3.5-star resort located a mere 4.8km from Stockbridge. Perfect for those seeking an LGBTQIA-friendly getaway, the resort offers a host of amenities tailored for families, including a children's playground, an arcade game room, and onsite mini-golf. Outdoor enthusiasts will appreciate the ski shuttle and ski lift proximity, making it an ideal choice for winter sports lovers. The welcoming environment and array of recreational options ensure that all guests can enjoy a fulfilling vacation experience.
  • The Black Swan Lee - Lenox, Ascend Hotel Collection: Nestled 6.4km from Stockbridge, this enchanting 3-star hotel is perfect for pet-friendly adventure seekers and families alike. The Black Swan offers a plethora of outdoor activities including motorboating, kayaking, and fishing right at your doorstep. If you’re feeling more adventurous, nearby mountain climbing and snowboarding options await. Child-friendly amenities such as cribs and safety features are available, ensuring a comfortable stay for families. With its charming ambiance and boundless recreational opportunities, this hotel is a delightful choice for your Berkshires adventure.
  • Holiday Inn Express Hotel & Suites Great Barrington by IHG: Located 8.0km from Stockbridge, this hotel caters to LGBTQIA-friendly business travellers seeking convenience and comfort. With facilities such as a 24-hour business centre, meeting rooms, and versatile conference spaces, it’s tailored for productive stays. The modern accommodations provide a restful retreat after a day of meetings or exploring the local area. Its commitment to inclusivity, paired with practical amenities, makes this hotel a compelling option for both work and leisure.

Where to stay near Stockbridge

Stockbridge, Massachusetts, offers a captivating blend of culture and romance, perfect for a relaxing getaway. Discover the town's architectural beauty and picturesque surroundings, with charming Berkshire farmhouse accommodations. Nearby, enjoy family-friendly activities and scenic views that enhance the tranquil atmosphere. Don't miss the chance to explore the enchanting landscapes and historical sites that make Stockbridge a memorable destination for every traveller seeking an idyllic escape.

  • Lenox: Situated a mere 8.0km from Stockbridge, Lenox is a charming town renowned for its cultural vibrancy. Visitors flock here primarily from June to August for a delightful mix of entertainment, romantic escapades, and family-friendly activities. The town boasts numerous attractions, including music concerts and theatre performances, alongside outdoor pursuits such as skiing in the winter months. Nature lovers will appreciate the scenic lakes and mountains that define the landscape, while the event conference venues add to Lenox's appeal as a hub for gatherings and celebrations.
  • Great Barrington: Located 11.3km away from Stockbridge, Great Barrington is a lively city that offers an exciting blend of adventure and sports experiences. With a steady influx of visitors, especially during the peak summer months of June to August, outdoor enthusiasts can indulge in a variety of winter sports, particularly skiing at the nearby resorts. The surrounding area is rich with natural beauty, featuring picturesque lakes and mountains, as well as the nearby national state park, making it an ideal destination for those seeking both thrill and tranquillity.
  • The Berkshires: Just 19.3km from Stockbridge lies The Berkshires, a stunning region celebrated for its breathtaking scenery and outdoor adventures. This area attracts visitors year-round, peaking in summer, and is perfect for those who seek to immerse themselves in nature. The Berkshires offers a myriad of activities, including skiing at its well-known resorts and exploring the expansive landscapes. With lakes and mountains as its backdrop, along with event conference venues, The Berkshires is a remarkable destination for those in pursuit of an adventurous yet scenic holiday.

Things to do in and around Stockbridge

Stockbridge, Massachusetts, is an ideal destination for culture lovers and couples seeking a romantic getaway. Visitors can enjoy a variety of activities, including captivating music concerts, engaging theatre performances, and thrilling experiences on the ski slopes. This charming town provides a delightful blend of entertainment and scenic beauty, making it a perfect spot for a memorable holiday.

Shopping

Discover unique gifts at the Berkshire Mountain Country Store, Charles H. Baldwin & Sons, and Hoffman's Pottery, all located just 6.4km from Stockbridge. If you're up for a drive, visit the Lee Premium Outlets, situated 17.7km away, featuring a variety of brand-name shops.

Recreation

Tanglewood Music Center offers a captivating concert experience, enveloped in a vibrant atmosphere just 8.0km from Stockbridge. For sports enthusiasts, Wyndhurst Golf & Club provides a splendid golf course set in picturesque surroundings. Lake Mansfield Park, located 9.7km away, is ideal for wellness and relaxation amidst nature.

Adventure

Experience thrilling skiing at Ski Butternut, located 11.3km from Stockbridge, where you can enjoy a vibrant winter sports atmosphere. For a scenic adventure, hike the Housatonic River Walk, also 11.3km away, offering stunning outdoor vistas. Alternatively, challenge yourself at Catamount Aerial Adventure Park, 17.7km from Stockbridge, with its exhilarating zipline courses.

Nightlife

Experience the vibrant nightlife in Stockbridge with a visit to Shakespeare and Company, offering a romantic theatre atmosphere just 8.0km away. Enjoy the local charm at the Berkshire Theatre Festival, or take in a show at the Mahaiwe Performing Arts Center, located 11.3km from Stockbridge.

*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 or November, and aim for a Tuesday stay, as Saturday is the priciest. Utilise Expedia to compare affordable hotels, including eco-friendly options, and take advantage of package deals that bundle flights and activities. Public transport is budget-friendly, and many attractions offer free activities that allow you to enjoy the beauty of Stockbridge without spending much. Be sure to search for deals on platforms like momondo for the best hotel prices.

  • 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: Expedia’s search tool enables you to specify your budget, desired location, and additional preferences. You can organise your results to display prices from lowest to highest, helping you to easily identify the most affordable hotels first. Furthermore, you have the option to refine your search by hotel category; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels that are available for booking.
  • Consider bundling your trip: You can potentially save money by combining your Stockbridge hotel reservation with your flights and activities through an Expedia package.

Find the best attractions in and around Stockbridge

Stockbridge, Massachusetts, offers a delightful blend of cultural, romantic, and entertainment experiences for visitors. With a variety of attractions such as historic houses, nature reserves, and scenic lakes, it caters to those seeking outdoor adventures, family fun, and cultural immersion. This charming town is perfect for travellers looking to explore its rich history and natural beauty.

  • National Shrine of the Divine Mercy: Nestled in Stockbridge, this serene shrine offers a spiritual retreat, inviting visitors to reflect and connect with their faith amidst its peaceful surroundings. The beautiful architecture and tranquil gardens create a perfect atmosphere for contemplation.
  • Norman Rockwell Museum: Dedicated to the beloved American artist, this museum showcases an extensive collection of Rockwell's iconic works. Visitors can explore his captivating illustrations that tell stories of everyday life, making it a delightful cultural experience.
  • The Mount: Located 6.4km from Stockbridge, this historic house was once the home of author Edith Wharton. The elegant architecture and stunning gardens provide insight into Wharton's life and work, making it a fascinating stop for literature enthusiasts.

Best time to go to Stockbridge

The best time to visit Stockbridge is dependant 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.

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

To reach Stockbridge, Massachusetts, you have several airport options. Bradley International Airport (BDL) in Hartford, CT, is situated 66.0km away and offers nearby hotels such as the DoubleTree by Hilton Hartford - Bradley Airport and Marriott Hartford Downtown. Albany International Airport (ALB) in Albany, NY, is located 64.4km from Stockbridge, with excellent hotel choices like the Park Manor Hotel and the Landing Hotel at Rivers Casino & Resort. Finally, Pittsfield Municipal Airport (PSF) is a mere 16.1km from Stockbridge, with nearby accommodations including the luxurious Miraval Berkshires Resort & Spa and the Stockbridge Country Inn, both offering convenient access to the airport.

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. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood is another good choice for your stay. See all available top hotels, or vacation rentals in Stockbridge.
What are some of the best holiday rentals that Stockbridge has to offer?
Spacious Living, Covered Porch & Forest Setting | Beaver Creek by AvantStay: This highly rated holiday home rental in Stockbridge offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. See all 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 Berkshire Mountain Lodge 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 48 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.

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