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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, (1,003 reviews)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
United States
Gary
The price is Rp2.503.945
Rp3.547.704 total
includes taxes & fees
4 Mar - 5 Mar
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 Rp5.200.643
Rp6.291.422 total
includes taxes & fees
24 Feb - 25 Feb
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (91 reviews)
  • cleanliness
    Seasonal mountain getaway with outdoor pool, near Jiminy Peak Mountain Resort.
"I’ve stayed here a few times. Super quaint and a reasonable distance to lots of great places. Very affordable."
United States
Jennifer
The price is Rp2.275.733
Rp2.496.479 total
includes taxes & fees
12 Feb - 13 Feb
The Springs Motel

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, (833 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 Rp1.890.562
Rp2.440.296 total
includes taxes & fees
1 Mar - 2 Mar
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,234 reviews)
"I great place to stay!!"
United Kingdom
Maricel
The price is Rp1.747.250
Rp2.136.029 total
includes taxes & fees
12 Feb - 13 Feb
Vacation Village in the Berkshires

Chatham Travel Lodge

Chatham Travel Lodge
2.5 star property
Old Chatham
7.8 out of 10, Good, (216 reviews)
  • cleanliness
    Relax in serene Old Chatham, close to local theatres and the Shaker Museum.
"Great friendly personable person at the front desk!!"
United States
Carolyn
The price is Rp1.949.212
Rp2.183.138 total
includes taxes & fees
22 Feb - 23 Feb
Chatham Travel Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (838 reviews)
  • cleanliness
    Experience the beauty of the Berkshires at a cosy lodge with golf access and pool.
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is Rp1.658.401
Rp2.227.858 total
includes taxes & fees
12 Feb - 13 Feb
Berkshire Mountain Lodge

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)
  • cleanliness
    Serene Lee retreat a short drive from Tanglewood Music Centre and local sights.
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is Rp1.414.141
Rp1.579.595 total
includes taxes & fees
1 Mar - 2 Mar
Quality Inn Lee - Lenox South

Berkshire Valley Inn

Berkshire Valley Inn
2.5 star property
Williamstown
9.2 out of 10, Wonderful, (566 reviews)
  • cleanliness
    Escape to the Berkshires with resort access, seasonal pool, and complimentary perks.
"We had a short but pleasant stay. "
United States
Scott
The price is Rp2.102.305
Rp2.348.275 total
includes taxes & fees
22 Feb - 23 Feb
Berkshire Valley 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, (1,000 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 Rp1.642.689
Rp1.834.884 total
includes taxes & fees
2 Mar - 3 Mar
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.4 out of 10, Exceptional, (71 reviews)
  • cleanliness
    Enjoy a charming escape in Copake Falls with easy access to local attractions.
"It was nice "
United States
Nicholas
Little Cat Lodge

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
  • cleanliness
    Charming Berkshire retreat with an outdoor pool and massage services in Lee.
"Well-run and elegant property. "
United States
Steven
The price is Rp4.013.034
Rp4.706.744 total
includes taxes & fees
22 Feb - 23 Feb
The Inn at Stockbridge

The Brooks Motel

The Brooks Motel
2.0 star property
Hillsdale
7.4 out of 10, Good, (127 reviews)
  • cleanliness
    Relax after scenic mountain adventures at this cosy winter sports retreat.
"The room is clean, exactly how you see it in the picture. Staff is very responsive, we enjoyed our stay and will definitely consider staying there again. "
United States
Michael
The Brooks Motel

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 Centre.
"The room and amenities were amazing. "
United States
Kathleen
The price is Rp2.003.156
Rp2.237.524 total
includes taxes & fees
1 Mar - 2 Mar
Hampton Inn & Suites Berkshires-Lenox

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,012 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 Rp1.556.983
Rp1.739.150 total
includes taxes & fees
22 Feb - 23 Feb
The Yankee, Trademark Collection by Wyndham

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (855 reviews)
  • cleanliness
    Experience Berkshires charm with on-site American dining and attentive service.
"So charming, clean, thoughtful touches and a really special place!"
United States
Juliana
The price is Rp1.484.243
Rp1.657.899 total
includes taxes & fees
8 Mar - 9 Mar
Berkshires Untold

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (823 reviews)
  • cleanliness
    Explore city centre Pittsfield from a stylish hotel with complimentary WiFi and parking.
"Great staff, beautiful hotel. Would definitely recommend "
United States
Shawn
The price is Rp2.503.945
Rp2.796.906 total
includes taxes & fees
12 Feb - 13 Feb
Hotel On North

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, (82 reviews)
  • cleanliness
    Relax in the heart of the Berkshires with an indoor pool and hot tub after a day out.
"it was a lovely hotel, hot tub was perfect after the day of skiing, everything very clean and new and lovely breakfast. All staff were very nice."
United States
Laura Pearson
The price is Rp2.219.100
Rp2.478.734 total
includes taxes & fees
1 Mar - 2 Mar
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
9.4 out of 10, Exceptional, (8 reviews)
  • cleanliness
    Stay amid picturesque Berkshires with a refreshing outdoor pool near Jiminy Peak.
"Healthy food too!"
United States
GEORGINA
The price is Rp2.828.281
Rp3.159.189 total
includes taxes & fees
8 Mar - 9 Mar
Huttopia Berkshires

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very good, (1,000 reviews)
  • cleanliness
    Experience a peaceful stay near Mahaiwe Performing Arts Centre.
"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 Rp1.271.298
Rp1.420.040 total
includes taxes & fees
23 Feb - 24 Feb
Quality Inn Great Barrington
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Stay near popular Stockbridge attractions

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 Historic Sites: Discover the rich history of Stockbridge through its well-preserved historic houses and landmarks.
  • Scenic Nature Reserves: Enjoy the serene beauty of picturesque lakes and tranquil nature reserves perfect for outdoor enthusiasts.
  • Cultural Experiences: Engage in local music concerts and theatre performances that showcase the vibrant arts scene.
  • Delightful Apple Orchards: Visit local orchards for a taste of fresh, seasonal produce and a true slice of Americana.
  • Varied Accommodation Options: Choose from charming bed and breakfasts to well-equipped hotels catering to all types of travellers.

Find great hotels near Stockbridge

Explore a delightful selection of hotel accommodations in Stockbridge, Massachusetts, where charming bed and breakfast options meet well-equipped hotels. Whether you seek a family-friendly retreat, a pet-friendly getaway, or an adventure-filled stay, Stockbridge has something for everyone. Discover local gems such as abba hotels and ac hotels, alongside accessible rooms to ensure a comfortable experience for all travellers.

  • The Whitlock: Nestled 8.0km from Stockbridge, The Whitlock is a charming hotel that offers a delightful blend of comfort and adventure. With a focus on outdoor activities, guests can explore nearby hiking and biking trails or enjoy skiing during the winter months. The hotel is centrally located near the city centre and historical district, allowing visitors to immerse themselves in local culture. The Whitlock’s inviting atmosphere and proximity to nature make it a perfect retreat for those seeking both relaxation and adventure.
  • The Dewey: Situated 9.7km from Stockbridge, The Dewey is a 3.5-star guesthouse tailored for the adventurous traveller. Known for its thrilling recreational options, guests can partake in a variety of adventure sports such as hiking, snowshoeing, rafting, cross-country skiing, and ziplining—all available nearby. The Dewey’s welcoming ambiance and focus on outdoor exploration provide an exhilarating escape for those looking to make the most of their vacation. This guesthouse promises an unforgettable experience filled with excitement and natural beauty.
  • Hampton Terrace Inn: Located 8.0km from Stockbridge, the Hampton Terrace Inn is a distinguished 4-star hotel that combines elegance with a range of amenities. Guests can enjoy a delightful dining experience at the on-site bar or explore local restaurants, ensuring a taste of the surrounding area's culinary delights. The inn features recreational activities such as outdoor tennis and nearby skiing opportunities. With entertainment options like flat-screen televisions and cable TV, guests can unwind in comfort after a day of exploration. Hampton Terrace Inn's historical charm and modern conveniences make it an excellent choice for discerning travellers.

Where to stay near Stockbridge

Stockbridge, Massachusetts, offers a charming blend of romance and culture, making it an ideal destination for a memorable getaway. Explore its rich historical sites, indulge in local apple orchards, and enjoy the serene scenery that surrounds the area. Nearby towns provide family-friendly activities and budget-friendly accommodations, ensuring a relaxing retreat. Immerse yourself in the essence of American life while enjoying the picturesque landscapes that make Stockbridge a must-visit location.

  • Lenox: Nestled a mere 8.0km from Stockbridge, Lenox offers a delightful blend of entertainment and romance, making it an ideal destination for families and couples alike. Known for its vibrant cultural scene, visitors flock to its music concerts and theatrical performances, especially during the peak months of June to August. The town is also a gateway to stunning natural attractions, including serene lakes and majestic mountains. Whether you’re exploring local places of worship or hitting the nearby ski fields, Lenox promises a memorable travel experience.
  • The Berkshires: Situated 19.3km away from Stockbridge, The Berkshires is a year-round playground for outdoor enthusiasts and adventure seekers. With its captivating scenery, the region invites visitors to engage in various outdoor activities, particularly skiing in the winter months. June to August sees the highest influx of tourists, with slightly fewer visitors between November and January. The area's natural beauty is complemented by its lakes and mountains, making it a picturesque backdrop for events and conferences, ensuring a well-rounded experience for every traveller.
  • Pittsfield: Also located 19.3km from Stockbridge, Pittsfield is an energetic city that attracts visitors eager for adventure and sports. Known for its ski resorts and fields, this city provides ample opportunities for winter sports and outdoor activities throughout the year, with a peak in tourism from June to August and a slight dip between October and December. Nearby lakes, mountains, and historic monuments enhance the local charm, making Pittsfield a vibrant destination for those looking to embrace both action and exploration.

Things to do in and around Stockbridge

Stockbridge is an idyllic destination perfect for romantic getaways and cultural experiences. Visitors can enjoy a variety of activities, including music concerts, theatre performances, and skiing. For those seeking adventure, the area also offers exciting sports opportunities and access to tennis facilities, ensuring a delightful holiday filled with entertainment and exploration.

Shopping

For unique gifts, explore the Berkshire Mountain Country Store, Hoffman's Pottery, and Charles H. Baldwin & Sons, all located a mere 6.4km from Stockbridge. If you're up for a drive, consider visiting larger shopping centres in nearby towns for a wider selection.

Recreation

At Tanglewood Music Center, immerse yourself in the soothing sounds of live music, just a short drive from Stockbridge. Wyndhurst Golf & Club offers invigorating rounds of golf amidst beautiful landscapes. For relaxation, Lake Mansfield Park provides a serene environment perfect for leisurely strolls and unwinding by the water.

Adventure

Experience the thrill of skiing at Ski Butternut, located 11.3km from Stockbridge, where you can enjoy a lively atmosphere filled with winter sports. For a scenic adventure, hike the Housatonic River Walk, also 11.3km away, offering beautiful views and a refreshing outdoor experience.

Nightlife

In Stockbridge, the nightlife is vibrant with venues like Shakespeare and Company, offering captivating theatre just 8.0km away. Locally, the Berkshire Theatre Festival brings romance and culture to life, while the Mahaiwe Performing Arts Center, 11.3km away, hosts unforgettable performances.

*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 during your visit to Stockbridge, consider travelling in the off-peak months of March to April and November, when accommodation prices drop. Tuesdays are typically the most affordable days to book a stay, while Saturdays are the priciest. Use Expedia's search tool to find the best deals by sorting hotels from lowest to highest price and filtering for eco-friendly options. Additionally, combining your hotel, flights, and activities into a package can lead to significant savings. Don't forget to look for free activities and local attractions with reduced admission prices to make the most of 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: Expedia's search tool enables you to specify your budget, chosen location, and additional preferences. You can arrange the search results to display prices from lowest to highest, ensuring you see the most affordable hotels first. Furthermore, you have the option to refine your search by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels available for booking.
  • Consider bundling your trip: You can save money by combining your Stockbridge hotel booking with your flights and activities by opting for an Expedia package.

Find the best attractions in Stockbridge

Stockbridge offers a charming blend of romance and culture, making it an ideal vacation spot. Visitors can explore historic houses, serene nature reserves, and picturesque lakes. The area's attractions cater to those seeking cultural experiences, outdoor adventures, and family-friendly activities, ensuring a delightful getaway for all types of travellers.

  • National Shrine of the Divine Mercy: Experience a serene atmosphere at this spiritual haven, dedicated to the message of Divine Mercy. Visitors can explore its beautiful grounds, participate in daily Mass, and enjoy moments of reflection amidst stunning architecture.
  • Norman Rockwell Museum: Immerse yourself in the world of American illustration at this renowned art museum. Featuring a vast collection of Rockwell's iconic works, it offers insights into his creative process and the cultural context of his art, making it a delightful experience for art lovers.
  • Naumkeag Museum: Discover the charm of this historic house and its exquisite gardens. Once a summer retreat for the Choate family, Naumkeag reveals the beauty of American landscape design and offers guided tours that delve into its rich history.

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.

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

When planning your visit to Stockbridge, Massachusetts, you can fly into several nearby airports. Hartford, CT (BDL-Bradley Intl.) is 66.0km away, with hotel options like the Sheraton Hartford Hotel at Bradley Airport, located right at the airport, and The Capitol Hotel, 17.7km away. Albany, NY (ALB-Albany Intl.) is 64.4km from Stockbridge, featuring hotels such as Oakcliff Bed and Breakfast, 11.3km away, and The Century House, 4.8km away. Lastly, Pittsfield, MA (PSF-Pittsfield Municipal) is only 16.1km from Stockbridge, with accommodations like the Hampton Terrace Inn, 8.0km away. Each airport offers convenient access to local hotels and transport services.

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. Two other options for your trip to 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, 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. Vacation Village in the Berkshires 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 44 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 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. 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.