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

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Our top choices for Stockbridge hotels

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A covered porch with wicker furniture and hanging flower baskets.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A bar with wooden floors and shelves filled with bottles.

1. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Patricia
CA $199
CA $292 total
includes taxes & fees
Sep 29 - Sep 30
The Red Lion Inn
A café with a display case, a frozen food section, and a marketplace sign.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
A multi-story building with a symmetrical facade, multiple balconies, and a central tower.
An indoor swimming pool with clear water, a lifeguard station, and a sign indicating no lifeguard on duty.

2. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
United States
Claudia
CA $162
CA $208 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn Club Vacations Oak 'n Spruce Resort
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.
A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.
An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".
A cozy library with bookshelves, a fireplace, and comfortable seating.

3. Berkshires Untold

Berkshires Untold
Lenox
United States
Christine
CA $194
CA $217 total
includes taxes & fees
Sep 28 - Sep 29
Berkshires Untold
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
A garden with wooden Adirondack chairs and a stone pathway.
A spacious lobby with a fireplace, seating area, and a bar.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

4. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
United States
Robert
CA $131
CA $177 total
includes taxes & fees
Aug 31 - Sep 1
Berkshire Mountain Lodge
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A lodge with a large building and a dock by a lake, surrounded by forest.
A dining area with large windows, wooden furniture, and a view of a lake.
A lakeside dock with kayaks and a covered boat ramp.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Rinat
CA $177
CA $197 total
includes taxes & fees
Sep 21 - Sep 22
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A living room with a fireplace, leather sofas, and a dog.
A stone fountain surrounded by trees in a park setting.
A hallway with wooden bookshelves, a door, and a bedroom with a bed and floral wallpaper.

6. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
United Kingdom
Michele
CA $522
CA $612 total
includes taxes & fees
Sep 17 - Sep 18
The Inn at Stockbridge
A wooden deck with wicker furniture and a view of a lake.
A two-story house with a balcony, a front porch, and a well-maintained lawn.
A view of a lakeside property with a deck and a white building.
A modern living room with a sofa, a coffee table, and a TV mounted on the wall.

7. Lakehouse Inn

Lakehouse Inn
Lee
United States
Kathleen
Lakehouse Inn
A two-story house with a brick entrance and a white facade.
A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.
A neatly arranged bedroom with a bed, bedside table, and a dresser.
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.

8. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Stockbridge
United States
Philippe
CA $459
CA $555 total
includes taxes & fees
Sep 28 - Sep 29
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A large house with a balcony and a grassy yard.
A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.
A room with a white desk, two floral chairs, a small round table with a plant, a hanging lamp, and two framed artworks on the wall.
A two-story building with a gabled roof and a chimney.

9. The Little Lion

The Little Lion
Great Barrington
United States
Anne
CA $153
CA $171 total
includes taxes & fees
Sep 13 - Sep 14
The Little Lion
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.
A loft bedroom with a sloped ceiling, a ceiling fan, a floor lamp, a bed with a patterned bedspread, a chair, and a small table.
A dining table set with a vase of flowers, a book, and cutlery.
A bed with a white lace bedspread, a tray with cookies and a bottle, and two glasses of red wine.

10. Brook Farm Inn

Brook Farm Inn
Lenox
United States
Carrie
CA $354
CA $407 total
includes taxes & fees
Aug 31 - Sep 1
Brook Farm Inn
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.

11. The Yankee Inn

The Yankee Inn
Lenox
United States
Karen
CA $177
CA $198 total
includes taxes & fees
Sep 16 - Sep 17
The Yankee Inn
A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.
A wooden cabin with a bed, a chair, and a table by a large window overlooking a lake.
A wooden deck with a dog silhouette against a backdrop of autumn foliage.
A wooden cabin with a staircase leading to a deck, surrounded by trees and a gravel path.

12. Prospect Berkshires

Prospect Berkshires
Egremont
United States
Kellee
CA $447
CA $546 total
includes taxes & fees
Sep 24 - Sep 25
Prospect Berkshires
A large, multi-story house with a reflective pond in front, surrounded by stone walls and trees.
A spacious loft-style living room with high ceilings, large windows, and a fireplace.
A stone bench by a calm lake with a stone wall and grass in the foreground.
A serene pond with a stone bridge, surrounded by lush greenery and a house in the background.

13. The Ponds at Foxhollow

The Ponds at Foxhollow
Lenox
United States
Lisa
The Ponds at Foxhollow
A large, two-story house with a well-maintained lawn and a fence.
A dining area with a table set for two, a view of a green landscape through large windows, and outdoor seating with a view.
A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.
A house with a fire pit in the yard, outdoor seating, and a large window overlooking the yard.

14. Devonfield Inn B&B

Devonfield Inn B&B
Lee
United States
Richard
CA $541
CA $604 total
includes taxes & fees
Sep 3 - Sep 4
Devonfield Inn B&B
A two-story building with a sign reading "Chambéry Inn".
A large, historic building labeled "Chambéry Inn" with a vintage turquoise truck parked in front.
A cozy room with a fireplace, a sofa, a table with a bottle and glasses, and a patterned pillow.
A hotel room with a large bed, a TV mounted above a fireplace, a desk, and a seating area with chairs.

15. Chambery Inn

Chambery Inn
Lee
United States
Richard
CA $374
CA $418 total
includes taxes & fees
Aug 30 - Aug 31
Chambery Inn
A dining table with pastries, a coffee pot, and a vase of sunflowers.
A bedroom with a wooden bed, bedside tables, a desk, and a chair.
A pool table in a room with a patterned rug, a shelf with decorative items, and a window with a view of greenery.
A large, two-story white building with a symmetrical facade, columns, and a central entrance.

16. Granville House

Granville House
Housatonic
United States
Nicole
CA $381
CA $425 total
includes taxes & fees
Sep 10 - Sep 11
Granville House
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.
A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.
A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

17. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
United States
Lawrence
CA $247
CA $275 total
includes taxes & fees
Sep 7 - Sep 8
Element by Marriott Lenox Berkshires
A snow-covered outdoor area with a patio, seating, and a covered dining area.
A modern living room with a fireplace, comfortable seating, and a large window with curtains.
A dining area with a glass table, red walls, and framed artwork.
A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.

18. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United States
Edward
CA $274
CA $314 total
includes taxes & fees
Aug 31 - Sep 1
The Cornell Inn, Lenox & The Berkshires
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.
A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

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

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
United States
Lisa
CA $223
CA $249 total
includes taxes & fees
Sep 7 - Sep 8
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
A covered outdoor area with stone pillars and a view of a road and green hills.
A modern restaurant with wooden flooring, bar area, and seating arrangements.
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.

20. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
United Kingdom
Laura
CA $246
CA $275 total
includes taxes & fees
Sep 7 - Sep 8
Courtyard by Marriott Lenox Berkshires
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Stay near popular Stockbridge attractions

Norman Rockwell Museum

9.4/10 (347 reviews)
You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area.
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National Shrine of the Divine Mercy

9.0/10 (83 reviews)
Learn about the local history of Stockbridge when you spend time at National Shrine of the Divine Mercy. While you're in the area, stroll along the lakeside.
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Naumkeag Museum

9.4/10 (10 reviews)
You can spend time browsing the exhibits at Naumkeag Museum during your travels in Stockbridge. While you're in the area, stroll along the lakeside.
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Berkshire Botanical Garden

9.4/10 (14 reviews)
Explore the great outdoors at Berkshire Botanical Garden, a lovely green space in Stockbridge. While you're in the area, stroll along the lakeside.
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Stockbridge Bowl

You can find out about the history of Stockbridge with a trip to Stockbridge Bowl. While in this relaxing area, you can enjoy the bars.
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Berkshire Theatre Festival

8.8/10 (3 reviews)
You can get tickets for a performance at Berkshire Theatre Festival on your trip to Stockbridge. Wander the lakeside in this quaint area.
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Schantz Galleries

7.2/10 (5 reviews)
You can spend an afternoon exploring the galleries in Schantz Galleries during your trip to Stockbridge. Wander the lakeside in this quaint area.
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Frelinghuysen Morris House and Studio

8.2/10 (10 reviews)
You can spend time exploring the galleries in Frelinghuysen Morris House and Studio during your trip to Stockbridge. Wander the lakeside in this family-friendly area.
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Learn more about Stockbridge

Norman Rockwell's Museum showcases the artist's iconic paintings of small-town American life in his former studio. Stroll down Main Street's historic district before hiking Monument Mountain for views that inspired Nathaniel Hawthorne's literary works.

See all hotels in Stockbridge
A calm lake reflecting a forest with autumn foliage.

Top Stockbridge Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent
"Amazing time. Stayed in the Presidential units. Worth it."
Marsha 5-night trip
Posted 1 hour ago
Holiday Inn Club Vacations Oak 'n Spruce Resort
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"
Dorothy 1-night trip
Posted 4 hours ago
The Red Lion Inn
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Room was"
Christopher 1-night trip
Posted 10 hours ago
The Cornell Inn, Lenox & The Berkshires
Berkshires Untold

Berkshires Untold

10/10 Excellent
"Chic bar and outdoor space. Nice remodel."
Kurt 1-night trip
Posted 10 hours ago
Berkshires Untold
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

10/10 Excellent
"Nice, well-maintained property, everything was very clean. The breakfast nook was not overly crazy crowded, which is really good traveling with young children. The staff even apologized for not having the waffle maker as a new one was being delivered. The hot tub was also a plus!"
Corinne 1-night trip
Posted 1 day ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good
"I am not a person who usually writes a review but I loved the place. Room was great. Staff was great. I had never been to an Indian restaurant but everywhere I went people raved about I so we went and it was wonderful. Only a few small issues. The fan in our bathroom room needs attention. Very loud. Something is failing. The wifi was very weak in my room. Kept cutting out. and just one other suggestion. The balcony on the upper level should have privacy screens on the sides. Other wise I would absolutely go back."
JAMES 2-night trip
Posted 1 day ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Yankee Inn

The Yankee Inn

10/10 Excellent
"One of the quietest rooms we have ever stayed in. The location was very convenient to sites in both Lenox and Stockbridge."
Stacia 1-night trip
Posted 1 day ago
The Yankee Inn
The Inn at Stockbridge

The Inn at Stockbridge

10/10 Excellent
"The property and grounds are beautiful and perfectly appointed. The staff are friendly and accommodating. The room was very comfortable. The gym is small but was very functional for our purposes and we appreciated having it available. The pool is beautiful but sadly we were unable to use it as it was closed the afternoon we came back early to swim and enjoy the sun. Breakfast was outstanding all 3 days and we appreciated having an access to machine for espresso and cappuccino. Would definitely stay here again."
Connie 3-night trip
Posted 3 days ago
The Inn at Stockbridge
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"Fine place to stay in the Lenox area."
Anthony 1-night trip
Posted 4 days ago
Best Western Plus Berkshire Hills Inn & Suites

More cheap stays in Stockbridge

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
CA $77
CA $86 total
Sep 29 - Sep 30
includes taxes & fees
FairBridge Inn Express
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
CA $108
CA $121 total
Sep 24 - Sep 25
includes taxes & fees
Howard Johnson by Wyndham Lenox
Quality Inn Great Barrington

Quality Inn Great Barrington

372 Main Street Great Barrington MA
CA $128
CA $143 total
Sep 21 - Sep 22
includes taxes & fees
Quality Inn Great Barrington
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St Pittsfield MA
CA $159
CA $178 total
Sep 20 - Sep 21
includes taxes & fees
Best Western Plus Berkshire Hills Inn & Suites
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

1055 South Street Pittsfield MA
CA $164
CA $183 total
Sep 8 - Sep 9
includes taxes & fees
9.4/10 Exceptional! (176 reviews)
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
CA $177
CA $198 total
Sep 16 - Sep 17
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
The Yankee Inn

Hotels in Stockbridge with star rating

Find out more about Stockbridge

Top reasons to visit Stockbridge

  • Charming Downtown: Explore art galleries and quaint shops in the picturesque downtown area.
  • Rich Cultural Scene: Enjoy live music concerts, theatre performances, and local cinema for entertainment.
  • Outdoor Adventures: Experience outdoor activities like skiing and nature preserves for thrilling adventures.
  • Relaxing Spa Experiences: Indulge in luxurious spa treatments for a relaxing retreat.
  • Welcoming Accommodations: Choose from cozy bed and breakfasts to inviting hotels for a comfortable stay.

Find great hotels near Stockbridge

Experience the charm of Stockbridge, Massachusetts, with a variety of lodging options that cater to every traveler's needs. From cozy bed and breakfasts to inviting hotels, you’ll find the perfect place to unwind after a day of adventure. Whether you're seeking a family getaway or a historic-themed vacation, Stockbridge offers delightful accommodations to enhance your stay. Discover the best Stockbridge hotels and inns for a memorable experience in this picturesque town.

  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Nestled in the heart of the Berkshires, this 3.5-star resort boasts a remarkable guest rating of 9.0. Perfect for family vacations and ski enthusiasts, it's conveniently located 4.8km from Stockbridge. The resort features a range of family-friendly amenities, including an onsite mini-golf course, a playground, and an arcade game room. Additionally, guests can enjoy easy access to ski shuttles and lifts, making it an ideal spot for winter sports lovers. Relax in spacious accommodations designed for family comfort.
  • The Black Swan Lee - Lenox, an Ascend Collection Hotel: This charming 3-star hotel is situated 6.4km from Stockbridge and boasts a stellar guest rating of 9.2. Designed for adventure seekers and families alike, The Black Swan offers thrilling outdoor activities, such as snow tubing, mountain climbing, and kayaking, all nearby. Pet-friendly amenities allow you to bring your furry friends along for the adventure. With services tailored for children, including first aid kits and cribs, this hotel ensures a safe and enjoyable stay for families.
  • Holiday Inn Express Hotel & Suites Great Barrington by IHG: Located 8.0km from Stockbridge, this budget-friendly hotel has a guest rating of 8.8, making it perfect for business travellers. With a focus on comfort and convenience, the Holiday Inn Express offers modern amenities and a complimentary breakfast to start your day right. The hotel’s strategic location provides easy access to local businesses and attractions, ensuring a productive stay while enjoying the charm of the Berkshires.

Where to stay near Stockbridge

Stockbridge, Massachusetts, offers a delightful blend of romance and culture, making it a perfect getaway for Canadian travellers. Explore the charming downtown area, where art galleries and quaint shops abound, or unwind in the serene surroundings of Central Stockbridge. Enjoy the picturesque scenery, ideal for family-friendly outings or budget-friendly adventures. Experience the unique vibe of Stockbridge, where historical charm meets modern relaxation, creating an unforgettable vacation experience.

  • Lenox: Located 8.0km from Stockbridge, Lenox is a charming city known for its vibrant cultural scene. This area sees a moderate flow of visitors, particularly peaking from June to August. Travellers flock to Lenox for its entertainment-themed and romantic experiences, making it perfect for couples and culture enthusiasts. Enjoy live music concerts, engaging theatre performances, and winter sports at nearby ski resorts. The city's scenic landmarks, including beautiful lakes and mountains, provide ample opportunities for outdoor exploration.
  • Great Barrington: Situated 11.3km from Stockbridge, Great Barrington offers a mix of adventure and relaxation throughout the year. Though visitor numbers peak in the summer months, the city maintains a steady flow of tourists, particularly those seeking a sports and ski experience. Great Barrington boasts thrilling ski fields and resorts, making it a popular destination for winter sports enthusiasts. The nearby national state park and picturesque lakes enhance the natural beauty, providing a backdrop for outdoor activities and serene hikes.
  • The Berkshires: Located 19.3km from Stockbridge, The Berkshires is a stunning region that attracts visitors year-round. With a peak in arrivals during the summer months, this area is celebrated for its outdoor and adventure experiences. Ski resorts and fields cater to winter sports lovers, while the breathtaking mountain scenery draws nature enthusiasts. The Berkshires also feature charming lakes and event venues, making it an ideal spot for both relaxation and recreation.

Things to do in Stockbridge

Stockbridge offers a delightful mix of romantic and cultural experiences, making it perfect for a vacation. Enjoy live music concerts, captivating theatre performances, and outdoor activities like skiing. For relaxation, indulge in a luxurious spa experience. Don't miss the local movie theatre for entertainment. Whether you're seeking leisure or adventure, Stockbridge has something for everyone to enjoy.

Shopping

In Stockbridge, you can explore charming local shops like The Red Lion Inn Gift Shop and Stockbridge General Store for unique souvenirs. If you're up for a drive, head to Lee Premium Outlets for brand-name deals and more extensive shopping options.

Recreation

Kripalu Centre for Yoga & Health offers transformative wellness programs in a tranquil setting, featuring yoga, meditation, and healthy cuisine. The nearby Berkshire Botanical Garden invites you to explore stunning landscapes and diverse plant collections, perfect for peaceful strolls and reflection amidst nature’s beauty.

Adventure

Explore the scenic trails of the Appalachian Trail, perfect for hiking enthusiasts seeking stunning views and a taste of nature. For a thrill, try white-water rafting on the Housatonic River, where you can experience exciting rapids amid beautiful landscapes.

Nightlife

Experience Stockbridge's charm at The Red Lion Inn, where you can enjoy a cozy drink by the fire. For a lively atmosphere, visit the nearby Berkshire Theatre Group for captivating performances, or unwind at the local pubs with craft beers and friendly conversations.

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

Booking tips and Expedia advantages for Stockbridge

  • 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: Utilize Expedia's search tool to refine your preferences, such as your budget, desired location, and preferred hotel type. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels currently available. To find the most affordable rates and special offers, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your Stockbridge hotel booking with your flights and activities through an Expedia package.

Find the best attractions in and around Stockbridge

Stockbridge, Massachusetts, offers a delightful mix of romance, culture, and entertainment for visitors. With attractions like historic houses, nature preserves, and libraries, there’s something for everyone. Whether you're seeking cultural experiences, outdoor adventures, or family-friendly activities, Stockbridge provides a charming backdrop for a memorable vacation. Explore the area's rich history and natural beauty while enjoying the warm hospitality that this quaint town has to offer.

  • National Shrine of the Divine Mercy: Immerse yourself in a serene atmosphere at this beautiful shrine, dedicated to the message of divine mercy. The serene gardens and peaceful ambiance provide a perfect setting for reflection and prayer, making it a unique spiritual experience.
  • Norman Rockwell Museum: Explore the iconic works of American illustrator Norman Rockwell at this charming museum, where you can delve into his art that captures the essence of American life. The exhibits highlight his storytelling talent and cultural impact, making it a must-visit for art lovers.
  • The Mount: Visit the stunning home of author Edith Wharton, where you can stroll through exquisite gardens and gain insights into her literary genius. This historic estate offers a glimpse into early 20th-century life and architecture, surrounded by breathtaking views.

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

For your visit to Stockbridge, Massachusetts, you have several airport options. Bradley International Airport (BDL) in Hartford, CT, is 66.0km away, with hotels like the DoubleTree by Hilton Hartford - Bradley Airport, just 1.6km from the airport. ALBany International Airport (ALB) is another choice, located 64.4km from Stockbridge, featuring nearby hotels such as The Landing Hotel at Rivers Casino & Resort, 12.9km away. Lastly, White Plains Airport (HPN) is 140.0km distant, with accommodations like The Opus Westchester, Autograph Collection, only 6.4km from the airport, offering convenient shuttle services. Choose the airport that best fits your itinerary for a seamless travel experience.

Frequently asked questions

What is the best area to stay in Stockbridge?
The best area to stay in Stockbridge is the town centre, particularly around Main Street, for a classic New England experience.This area is the heart of Stockbridge, offering a quintessentially charming village feel. Main Street is lined with historic buildings, art galleries, and local shops, all within easy walking distance. The Red Lion Inn, a well-known landmark, is also located here.Couples looking for a relaxing and cultured getaway will find the town centre ideal. You're just a short stroll from the Norman Rockwell Museum, which houses an extensive collection of his works, and the Berkshire Theatre Group's Unicorn Theatre, offering live performances. The area's focus on art and history provides plenty of activities for a pleasant trip.For those prioritising a tranquil setting with convenient access to nature, the areas just outside the town centre, towards the Housatonic River, offer a peaceful alternative.
What are the best hotels in Stockbridge that travellers recommend?
For a highly recommended hotel in Stockbridge, The Red Lion Inn is an excellent choice.This 3.5-star hotel, with an 8.8 rating, offers comfortable and quiet rooms, often praised for their Frette Italian sheets. Guests consistently highlight the excellent and friendly staff and service, as well as the good to excellent food available. The hotel provides amenities such as bathrobes, air conditioning, and 24-hour room service. For entertainment, there is evening entertainment, concerts or live shows, and a fireplace to enjoy. Its location is also considered great, being just 0.3 km from Mission House and 0.7 km from the Berkshire Theatre Festival.
What are the best family hotels in Stockbridge?
For families visiting Stockbridge, two excellent choices are the Taggart River House and The Red Lion Inn.The Taggart River House, with an outstanding 9.8 rating, offers modern luxury in a natural setting. This accommodation can sleep up to 10 people, making it ideal for larger families, and boasts stunning river views. Families will appreciate the convenience of a travel cot and stair gate for children, a fully equipped kitchen, and outdoor spaces like a patio and deck. It is also well-located, being just 0.9 km from Berkshire Botanical Garden and 1.3 km from the Norman Rockwell Museum.Another highly regarded option is the 3.5-star The Red Lion Inn, which has an 8.8 rating. This hotel is located in a historical district and is part of Historic Hotels of America. It caters well to families by offering complimentary cots and connecting rooms. Guests frequently praise the comfortable and quiet rooms, excellent food, and friendly staff and service. The location is also a key feature, being only 0.3 km from Mission House and 0.7 km from the Berkshire Theatre Festival. For those interested in winter activities, skiing is available nearby, with options for downhill, cross-country, and lessons. Find more child-friendly accommodations in Stockbridge
What are the best spa hotels in Stockbridge?
For travellers seeking the best spa hotels in Stockbridge, The Red Lion Inn is an excellent choice.This 3.5-star hotel, with an impressive 8.8 rating, is known for its on-site spa and offers various massage treatments, though advance notice is recommended. Guests frequently praise its comfortable and quiet rooms, excellent food, and friendly service from the staff. As a historic hotel located within a historical district, it provides a unique stay and is also conveniently close to several skiing areas. See all spa hotels in Stockbridge
What hotels in Stockbridge offer free breakfast?
For hotels in Stockbridge offering complimentary breakfast, consider The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood or Tanglewood Suites.The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, a 4.5-star establishment with an excellent 9.2 rating, provides free continental and full breakfast options. Guests can also enjoy free self-parking and complimentary WiFi. It is conveniently located just 0.6 km from Chesterwood.Another excellent option is Tanglewood Suites. This hotel offers free continental breakfast, free WiFi, and free self-parking. It is located 0.7 km from Mission House and 0.8 km from the National Shrine of the Divine Mercy. Find more hotels with free breakfast in Stockbridge
What are the top pet-friendly hotels in Stockbridge?
For top pet-friendly accommodation in Stockbridge, The Red Lion Inn is an excellent choice.This 3.5-star hotel, with an 8.8 rating, is top for its comfortable and quiet rooms, as well as its excellent and friendly staff and service. Guests also appreciate the excellent food options available. The Red Lion Inn is conveniently located in a historical district, making it a great base for exploring the area. It is also very close to the Mission House, just 0.3 km away, and the Berkshire Theatre Festival, 0.7 km away. For those interested in winter sports, skiing, ski rentals, and ski lessons are all available nearby. See more pet-friendly hotels in Stockbridge
What are the best budget hotels in Stockbridge?
For budget-friendly accommodation in Stockbridge, you might consider Tanglewood Suites or Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10.Tanglewood Suites offers excellent value with complimentary WiFi, free self-parking, and a free continental breakfast, including free toiletries. Its location provides lovely mountain views and is conveniently close to Mission House at 0.7 km and the National Shrine of the Divine Mercy at 0.8 km.Another highly-rated option is Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10, which boasts an impressive 9.8 review rating. This accommodation is well-suited for families, offering a kitchen, a patio, a deck, a travel crib, and a stair gate for children. Guests can also enjoy onsite golf and parking. It is located 0.9 km from the Berkshire Botanical Garden and 1.6 km from the National Shrine of the Divine Mercy. View all budget hotels in Stockbridge
What are the most romantic hotels in Stockbridge for couples?
For a romantic stay in Stockbridge, The Red Lion Inn is an excellent choice for couples.This 3.5-star hotel, with an 8.8 rating, is celebrated for its comfortable and quiet rooms, making it ideal for a peaceful getaway. Guests frequently praise the excellent food and friendly service, ensuring a delightful experience. Its location is a great base for exploring local attractions such as the Mission House, which is just 0.3 km away, or the Naumkeag Museum, located 0.9 km from the hotel. The Red Lion Inn is also recognised as one of the Historic Hotels of America, adding to its special appeal. See all romantic hotels in Stockbridge
What are the best hotels in Stockbridge near Berkshire Botanical Garden?
For hotels in Stockbridge near the Berkshire Botanical Garden, Taggart River House is an excellent option.The Taggart River House, with an impressive 9.8 rating, is located just 0.9 km from the Berkshire Botanical Garden. This property offers modern luxury with stunning river views and features a well-equipped kitchen and a patio or deck for relaxation. It is also well-suited for families, providing a travel crib and stair gate for children.While not as close, The Red Lion Inn, a 3.5-star hotel with an 8.8 rating, is another highly-rated option in Stockbridge, known for its comfortable and quiet rooms, excellent food, and friendly staff.
When is the best time to go to Stockbridge?
The best time to go to Stockbridge is during the autumn months, specifically from late September through October, to experience the spectacular fall foliage.This period offers clear, crisp air and the Berkshire Hills ablaze with vibrant reds, oranges, and yellows. It's also an excellent time for outdoor activities like hiking and scenic drives. Weekends in October can be particularly busy as many visitors come to witness the natural beauty.For couples seeking a romantic getaway, the autumn provides a picturesque backdrop for strolls through the town, visits to the Norman Rockwell Museum, and cosy evenings by a fireplace. The natural beauty of the season enhances the historic charm of Stockbridge.Families might find late spring or early summer (May to June) more appealing. The weather is pleasantly warm, ideal for exploring the Berkshire Botanical Garden or enjoying the outdoor spaces at The Mount, Edith Wharton's home. The crowds are typically smaller than in autumn, offering a more relaxed experience.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Stockbridge.
How much is the nightly rate at a Stockbridge hotel?
Prices for hotels in Stockbridge often vary, but you can find a great deal from CA $86 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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