Great Barrington Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £335 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Packages with flights are ATOL protected

Your Great Barrington Holiday

Say goodbye to the worries of planning and hello to a Great Barrington holiday package. With the finer details organised before you take off, you can focus on discovering the best of this city, starting with Canann Village Historic District, which is good for dining, culture and shopping. Fill your spare time with visits to Ski Butternut, Housatonic River Walk and Lake Buel, some of the things you simply have to see during a trip to Great Barrington. Expedia is here to help you escape the everyday. Tailor your holiday to Great Barrington to suit your travel style, whatever that may be!

Things to do in and around Great Barrington

Great Barrington is an ideal destination for ski enthusiasts and adventure seekers, offering a variety of activities such as skiing at local resorts and exploring recreational experiences. Visitors can also enjoy holiday events, Halloween festivities, and golfing at nearby clubs, as well as exploring fascinating exhibits. This charming town promises an exciting blend of outdoor sports and cultural experiences for all types of travellers.

Shopping

For a delightful shopping experience in Great Barrington, visit Hoffman's Pottery and Charles H. Baldwin & Sons, both offering unique gifts. If you're up for a drive, the Lee Premium Outlets boasts a variety of brand-name shops and a vibrant atmosphere, perfect for finding souvenirs.

Recreation

Experience the enchanting Tanglewood Music Center, where you can enjoy captivating concerts amidst beautiful surroundings. For a tranquil escape, visit Lake Mansfield Park for relaxation and leisurely strolls. Finally, immerse yourself in the cultural richness of the Mahaiwe Performing Arts Center, perfect for families and a romantic night out.

Adventure

Embark on the Housatonic River Walk for a scenic hike amidst nature's beauty. Experience exhilarating skiing at Ski Butternut, perfect for sports enthusiasts. For a thrilling challenge, venture 9.7km to Catamount Aerial Adventure Park, where ziplines and ropes courses await in a stunning outdoor setting.

Nightlife

Great Barrington’s nightlife offers a charming blend of local pubs and vibrant bars. Enjoy a relaxed evening at The Castle Street Café or unwind with craft cocktails at The Well. For live music, The Mahaiwe Performing Arts Center features an array of performances that add to the town's lively atmosphere.

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

Find the best attractions near Great Barrington

Great Barrington, Massachusetts, is an ideal destination for sports and adventure enthusiasts, offering a blend of historic houses, national parks, and nature reserves. Visitors can immerse themselves in the local culture while enjoying a variety of outdoor activities. The area is also known for its seasonal events and attractions that cater to diverse interests, making it a charming spot for a memorable vacation.

  • Norman Rockwell Museum: Located 11.3km from Great Barrington, this museum celebrates the life and works of iconic American illustrator Norman Rockwell. Visitors can explore a vast collection of his artwork, offering a glimpse into American culture and storytelling through art.
  • Ventfort Hall Mansion and Gilded Age Museum: A mere 19.3km away, this historic mansion transports you to the opulent Gilded Age. Discover the architectural grandeur and rich history of the era, with guided tours showcasing its stunning interiors and fascinating stories.
  • National Shrine of the Divine Mercy: Just 11.3km from Great Barrington, this serene shrine offers a peaceful retreat for reflection and spiritual connection. Its beautiful grounds and chapel provide a tranquil atmosphere for visitors seeking solace and inspiration.

Best time to go to Great Barrington

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January23.2°F (-4.9°C)Light RainMostly CloudyAverageAverage
February24.8°F (-4.0°C)Light RainMostly CloudyAverageAverage
March32.5°F (0.3°C)Light RainMostly CloudyAverageSlightly Low
April44.2°F (6.8°C)Light RainMostly CloudyAverageSlightly Low
May55.9°F (13.3°C)Light RainMostly SunnyAverageAverage
June63.7°F (17.6°C)Light RainMostly SunnySlightly HighAverage
July69.8°F (21.0°C)Light RainMostly SunnySlightly HighSlightly High
August67.8°F (19.9°C)Light RainMostly SunnySlightly HighSlightly High
September60.8°F (16.0°C)Light RainMostly SunnyAverageAverage
October49.8°F (9.9°C)Light RainMostly SunnySlightly LowSlightly High
November37.8°F (3.2°C)Light RainMostly SunnySlightly LowSlightly Low
December29.7°F (-1.3°C)Light RainMostly CloudySlightly LowAverage

Tips to save on your trip to Great Barrington

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Great Barrington.
  • Consider traveling during the off-peak season (typically March to April and November) for more affordable package holidays to Great Barrington.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Great Barrington Essential Information

Language
English
Currency
U.S dollars
Population
2,200
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Norman Rockwell Museum, Ski Butternut and Catamount Ski Area

Top hotels in Great Barrington

Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Fully refundableReserve now, pay when you stay
The price is £56 per night from 30 Apr to 1 May
£56
30 Apr - 1 May
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
I like this hotel for the great location, breakfast included, and clean adequate rooms. The staff are wonderful. Very well priced.

Reviewed on 12 Apr 2026

Quality Inn Great Barrington
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 out of 5
415 Stockbridge Rd Great Barrington MA
Fully refundable
The price is £89 per night from 20 Apr to 21 Apr
£89
20 Apr - 21 Apr
includes taxes & fees
8.8/10 Excellent! (754 reviews)
This was a very nice stay. The gentleman that checked us in was friendly, funny, knowledgeable and very welcoming.

Reviewed on 1 Apr 2026

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

3 out of 5
249 Stockbridge Rd Great Barrington MA
Fully refundableReserve now, pay when you stay
The price is £126 per night from 26 Apr to 27 Apr
£126
26 Apr - 27 Apr
includes taxes & fees
9.4/10 Exceptional! (777 reviews)
Smooth as silk - staff was beyond exceptional. Gym was under construction but can’t fault them for that. Pool was working! It really was perfect. Thank you!

Reviewed on 9 Apr 2026

Fairfield Inn & Suites by Marriott Great Barrington 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.

Great Barrington Ski Holiday Packages

If snow-covered peaks are beckoning, score a pile of savings with one of our Great Barrington ski holiday packages. Show off your slalom skills during the day, check out the après-ski scene after dark and do things your way with Expedia. Among the most renowned winter destinations in United States of America, Great Barrington has around 22 ski runs operating from December to March each year. Enjoy a little time in the ski village and rent any gear you need for downhill skiing. If you're a newbie, there's at least one beginners' area where you can practice the basics. When you're ready to leave the slopes, head on over to the day spa here. It's the perfect way to soothe sore muscles after hours of endless fun. A family ski holiday in Great Barrington is a wonderful opportunity to have new experiences with your brood. Once you've all mastered the slopes, have a go at snowboarding and tobogganing.

How To Get Around

Reserve one of Expedia's Great Barrington holiday packages and your next fabulous adventure is just a plane ride away. After disembarking at Albany International Airport, it's one hour to reach this terrific ski destination. Driving from the centre of Great Barrington to the ski slopes takes 10 minutes and you can park for free. For safety on the roads in the winter months, snow chains are recommended. Get serious savings on your ski holiday when you book everything together. Pick from a season-pass ticket or a full-day ticket, then combine your flights, hotel and a car rental into a package to get the best price every time. Look through our Great Barrington ski package deals for a little inspiration.

Great Barrington Resort Ski Info

Average yearly snowfall
10 ft
Elevation of lowest ski lift
820 ft
Cost of 1-day lift pass
Under £65
Easy runs
8
Moderate runs
8
Advanced runs
6
Longest run
1.5 mi

Popular places to visit

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.