Great Barrington vacation rentals

We found 665 vacation rentals — enter your dates for availability

Select from 98 homes, 14 cottages, and other vacation rentals in Great Barrington to find one that's perfect for your trip. Whether you’re staying in a vacation home with your kids or with friends, you'll have the best amenities for spending time at your home away from home, which might include air conditioning and a pool. Whatever you're looking for, you'll be able to choose a rental that has what everyone needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Great Barrington

Showing deals for:May 22 - May 29

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10 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)

Best of the Berkshires & Hudson Valley

Canaan

9% off
Price is $506
$3,544 for 7 nights
All fees included
Best of the Berkshires & Hudson Valley

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Find out more about Great Barrington

Why visit Great Barrington

  • Outdoor Adventure: Great Barrington offers thrilling activities like skiing and hiking in its beautiful natural parks.
  • Charming Downtown: Explore the vibrant downtown area filled with local shops, cozy cafes, and a welcoming atmosphere.
  • Historic Attractions: Visit historic houses and sites that reflect the rich cultural heritage of the region.
  • Family-Friendly Atmosphere: The town is ideal for families and romantic getaways, providing a relaxing environment.
  • Diverse Accommodations: Choose from cozy vacation rentals, charming cottages, and modern condos for a comfortable stay.

Popular types of accommodation in Great Barrington

Discover the perfect getaway with vacation rentals in Great Barrington. From cozy houses and charming cottages to modern condos, there’s something for everyone. Enjoy beautiful bedrooms and friendly apartments packed with amenities to make your stay comfortable. Whether you’re traveling with family or friends, you’ll find the ideal accommodation to relax and explore all that this picturesque town has to offer.

  • Houses: The top choice for travelers in Great Barrington, these spacious homes provide a cozy and comfortable atmosphere, ideal for families or groups.
  • Condos: A popular option for those seeking modern amenities and convenient locations, condos offer a blend of comfort and style.
  • Cottages: Perfect for a charming getaway, cottages are quaint and provide a serene setting for relaxation.
  • Apartments: A versatile choice, apartments cater to solo travelers and couples looking for a convenient home base.
  • Cabins: Rustic and inviting, cabins offer a unique experience amidst nature, perfect for a peaceful retreat.**

Top attractions in and around Great Barrington

Great Barrington, Massachusetts, is an ideal destination for ski enthusiasts and adventure seekers. Visitors can explore a variety of attractions, including historic houses, national and state parks, and nature reserves. Whether you're looking for outdoor activities, cultural experiences, or thrilling adventures, Great Barrington has something for everyone, making it a perfect spot for a memorable vacation.

  • National Shrine of the Divine Mercy: Located 7 miles from Great Barrington, this serene shrine offers a peaceful atmosphere for reflection and prayer. Its beautiful architecture and tranquil gardens create a spiritual retreat that attracts visitors seeking solace and inspiration.
  • Housatonic River: Just 0.1 mile away, the Housatonic River is perfect for outdoor enthusiasts. Enjoy scenic views while kayaking or fishing, or simply relax along its banks in a picturesque natural setting.
  • Lake Buel: Situated within Great Barrington, Lake Buel features a lovely beach and stunning scenery, making it an ideal spot for swimming, picnicking, or a romantic sunset stroll.

Things to do recommended for couples

For a romantic getaway in Great Barrington, enjoy skiing at Ski Butternut or Catamount Ski Area for some thrilling outdoor fun. Unwind at Les Trois Emme Winery, where you can savor delightful wines in an enchanting atmosphere, perfect for couples looking to create lasting memories.

Things to do recommended for families

Families visiting Great Barrington can enjoy a day at Lake Mansfield Park, perfect for relaxation and recreation. Just a short drive away, Tyringham Cobble and Goose Pond Reservation offer beautiful natural settings for hiking and exploring, making for memorable family adventures.

Things to do recommended for groups

In Great Barrington, your group can enjoy the scenic Housatonic River Walk for a refreshing hike, experience culture and entertainment at the Mahaiwe Performing Arts Center, or embark on an exhilarating adventure at Catamount Aerial Adventure Park, located 6 miles away, for ziplining and ropes courses.

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

What do I need to keep in mind when booking a vacation in Great Barrington

If you're traveling with a group, your family, pets, or planning an extended stay, it's important to set the right filters based on your priorities. Here are some useful Vrbo booking tips just for you.

  • Traveling to Great Barrington with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Great Barrington with young kids: Traveling with little ones can be a bit tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are family-friendly.
  • Taking your pets with you to Great Barrington: For many families, a vacation wouldn't feel complete without their furry companions. If you can relate, take a look at Vrbo listings that welcome pets. Most of these pet-friendly homes come equipped with feeding bowls and cozy beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Great Barrington: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Great Barrington

Great Barrington, Massachusetts, offers a unique blend of adventure and relaxation, perfect for your vacation. Explore charming neighborhoods and the vibrant downtown area, where you'll find friendly local shops and cozy cafes. The picturesque scenery invites outdoor enthusiasts to ski and engage in various sports, while the welcoming atmosphere makes it ideal for families and romantic getaways alike. Discover the magic of Great Barrington and its surrounding areas for an unforgettable experience.

  • Lenox: Located 12 miles from Great Barrington, Lenox is a charming city known for its rich cultural scene and romantic ambiance. Visitors flock to Lenox for entertainment-themed experiences, with venues offering everything from live music concerts to captivating theater performances. Outdoor enthusiasts can enjoy skiing at nearby resorts, while the area’s stunning lakes and mountains provide the perfect backdrop for family activities. Notable attractions include the iconic Tanglewood music venue, which hosts summer concerts, and the picturesque Kennedy Park, ideal for leisurely hikes and picnics.
  • The Berkshires: Just 11 miles from Great Barrington, The Berkshires is a haven for outdoor adventurers and nature lovers. This region is characterized by its breathtaking scenery, featuring rolling hills, lush forests, and pristine lakes. It's a popular destination for skiing, with numerous ski fields and resorts catering to all skill levels. Visitors can partake in hiking, biking, and exploring the vibrant local arts scene. Noteworthy attractions include the scenic Mount Greylock and the Norman Rockwell Museum, which celebrate the area’s artistic heritage.
  • Stockbridge: Situated 7 miles from Great Barrington, Stockbridge offers a delightful mix of culture and charm. This quaint town is renowned for its cultural experiences, with a focus on art and entertainment. Visitors can enjoy music concerts and theatrical performances, with the beautiful Mahaiwe Performing Arts Center at the heart of it all. Outdoor lovers will appreciate the stunning landscapes, highlighted by the tranquil Stockbridge Bowl and the historic Stockbridge Monuments. Additionally, the Norman Rockwell Museum showcases the life and work of the beloved artist who called Stockbridge home.

Best time to go to Great Barrington

If you're planning a trip to Great Barrington, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

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 HighAverage
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 Low
November37.8°F (3.2°C)Light RainMostly SunnySlightly LowSlightly High
December29.7°F (-1.3°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is simple

Are you hoping to cut costs on your upcoming trip? Being open to adjusting your travel dates can help, as prices can vary significantly. Additionally, booking a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Unlock savings with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll earn OneKeyCash on the full booking amount. Being the organizer truly has its benefits. By joining our One Key rewards program, you can unlock exclusive savings for members and accumulate OneKeyCash on eligible stays. Sign up today and begin earning.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient way for you to plan new getaways, manage your existing travel arrangements, or review your bookings. Your saved and booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To check out Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The lively city of Great Barrington awaits you

The area's live music and theater scene are just a few of the reasons to vacation in Great Barrington. Well known for its rock climbing, hiking and cafes, this scenic city won't disappoint. With a vacation rental, you get a home away from home. Many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in and around Great Barrington

Do you want to discover attractions to see while you're in the area? You'll be sure to enjoy Great Barrington for its hiking and skiing. Venture out of your vacation home and experience everything that makes Great Barrington a fun spot to vacation. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Ski Butternut (2.3 mi / 3.7 km)
  • Catamount Ski Area (6.3 mi / 10.1 km)
  • Wyndhurst Golf & Club (11.3 mi / 18.1 km)
  • Otis Ridge (13.4 mi / 21.5 km)
  • Bousquet Ski Area (15.7 mi / 25.3 km)
  • Hudson Chatham Winery (16.3 mi / 26.3 km)

Exploring the natural landscape of Great Barrington

Whether you're looking for exciting outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Great Barrington. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Housatonic River Walk (0.1 mi / 0.2 km)
  • Housatonic River (0.1 mi / 0.2 km)
  • Lake Mansfield Park (0.7 mi / 1.1 km)
  • Lake Buel (4.8 mi / 7.7 km)
  • Naumkeag Museum (6.9 mi / 11.1 km)
  • Berkshire Botanical Garden (7.4 mi / 11.8 km)

Seasonal weather averages in Great Barrington

Travelers enjoy Great Barrington for its skiing. To make the most of the cold weather activities, you might consider visiting in January, March, February or November, when snowfall averages 7 inches and temperatures average 28°F.

Transportation options to and around Great Barrington

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 16.2 mi (26.1 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Hudson, NY (HCC-Columbia County), which is 19.2 mi (30.9 km) away.

Frequently asked questions

What is the best area to stay in Great Barrington, Massachusetts, United States of America when booking a vacation rental?
When looking for the best area to stay in Great Barrington, Massachusetts, consider the charming downtown neighborhood. This area offers a delightful mix of boutique shops, local eateries, and art galleries, making it an ideal spot for those who appreciate a vibrant setting. A standout attraction is the Mahaiwe Performing Arts Center, which hosts a variety of performances, from concerts to film screenings, providing a cultural hub right at your doorstep. Additionally, the nearby Berkshire Botanical Garden offers a serene escape with its beautiful landscapes and seasonal exhibits, great for a leisurely stroll.

Another excellent option is the Housatonic neighborhood, just a short distance from downtown. This area boasts a more laid-back vibe while still being close to the action. Here, you can explore the scenic Housatonic River, which is great for kayaking and fishing enthusiasts. The neighborhood is also near the historic Berkshire Museum, where you can enjoy art, science, and history exhibitions—all in a family-friendly setting.

Both neighborhoods have a variety of vacation rental options, ensuring that you'll find a cozy spot that suits your needs.
How much does it cost to rent a vacation home in Great Barrington?
Prices for vacation rentals in Great Barrington vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Great Barrington to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Great Barrington vacation house rentals?
You can find great discounts on house rentals in Great Barrington on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Great Barrington ski resort rentals?
For the best ski resort rentals in Great Barrington, travelers should focus on the area surrounding Butternut Ski Area, which is just a short drive away. In the nearby neighborhoods of Housatonic and Great Barrington itself, visitors can find a range of cozy cabins and modern vacation homes that cater to both families and groups. Many properties feature amenities such as fireplaces, spacious living areas, and fully equipped kitchens, superb for relaxing after a day on the slopes.

Additionally, the downtown area of Great Barrington offers a vibrant setting with local shops, restaurants, and art galleries, enhancing the overall experience. Rentals here often boast easy access to both the ski area and the cultural attractions of the town, with some properties providing outdoor spaces like decks or patios for enjoying the beautiful mountain views.

For those looking for a more rustic experience, the surrounding countryside offers charming lodges and chalets, frequently equipped with amenities such as hot tubs, fire pits, and game rooms, ideal for unwinding after skiing. The region also provides ample opportunities for winter activities beyond skiing, including snowshoeing and cross-country skiing in nearby parks. See all ski-in-/ski-out rentals in Great Barrington.
What is the most popular type of vacation rental accomodation in Great Barrington?
In Great Barrington, vacation houses are the most popular type of rental, with about 84 available throughout the area. These homes are often situated in serene neighborhoods, offering a spacious and comfortable environment for families or groups. Most vacation houses come equipped with amenities like fully stocked kitchens, multiple bedrooms, and outdoor spaces for relaxing and enjoying the scenic surroundings. Additionally, there are around 12 cottages, several apartments, cabins, and condos, providing diverse options for travelers. Cottages typically offer a quaint, rustic charm, while cabins and condos can be found in more secluded or urban settings, appealing to different tastes and preferences.
Are there any family house rentals in Great Barrington?
In Great Barrington, Massachusetts, visitors can find a number of family-friendly vacation rentals—approximately 82 homes are available throughout the area. This charming town offers various accommodations, from cozy cabins to spacious houses, making it an excellent choice for families. Many properties feature generous living spaces, well-equipped kitchens for preparing family meals, and outdoor areas great for kids to play or relax after a day of activities.

Neighborhoods like Housatonic and downtown Great Barrington provide easy access to local attractions, including the picturesque Berkshire Hills and vibrant downtown shops and restaurants. Families can enjoy nearby parks with playgrounds and hiking trails, as well as cultural venues like the Mahaiwe Performing Arts Center, which often hosts family-friendly events.
Can I rent a vacation home with a pool or hot tub in Great Barrington?
In Great Barrington, you can find a selection of vacation homes available for rent that feature pools and hot tubs, with around 21 options to choose from. This charming town in the Berkshires offers a picturesque setting, making it an ideal spot for relaxation and outdoor activities. Many of these properties come equipped with amenities such as private swimming pools, hot tubs, spacious outdoor decks, and fully equipped kitchens, superb for families or groups looking to unwind after a day of exploring the scenic surroundings.

Travelers can enjoy the nearby attractions, including hiking trails, cultural events, and local dining options. Find your rental in Great Barrington with a pool or a hot tub.
Can I find long-stay vacation rentals in Great Barrington?
A long-stay vacation rental in Great Barrington is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Great Barrington?
In Great Barrington, travelers will find a variety of pet-friendly house rentals available, with around 65 options to choose from. The town is known for its charming New England atmosphere and offers a range of vacation homes that often come equipped with amenities like spacious backyards, modern kitchens, and cozy living areas, making them suitable for families and groups traveling with pets.

The area is especially inviting for outdoor enthusiasts, with close access to parks and nature trails. Nearby, the picturesque Monument Mountain features hiking paths that are superb for walks with pets while enjoying stunning views of the surrounding landscape. Additionally, the downtown area offers pet-friendly cafes and local shops, creating a welcoming environment for both travelers and their furry companions. See all pet-friendly rentals in Great Barrington.
Are there any remote work vacation rentals in Great Barrington?
In Great Barrington, Massachusetts, there are numerous remote work vacation rentals available, with around 106 options to choose from. This charming town, located in the Berkshires, offers a variety of properties that are well-suited for remote work. Many rentals come equipped with high-speed internet, Wi-Fi, and designated workspaces or desks, ensuring that guests can maintain productivity during their stay.

Travelers can expect comfortable accommodations that often feature modern amenities such as fully equipped kitchens, spacious living areas, and, in some cases, outdoor spaces for relaxation. Great Barrington itself is known for its vibrant arts scene, local shops, and proximity to outdoor activities like hiking and skiing in the winter months. The area also boasts lovely parks and cultural attractions, making it an ideal destination for those looking to balance work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Great Barrington vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Great Barrington with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Great Barrington?
In Great Barrington, travelers can expect a variety of popular rental amenities that enhance their stay. Most vacation rentals come equipped with kitchens, allowing guests to prepare their own meals and enjoy the local produce. Many properties also feature decks or patios, providing an inviting outdoor space to relax and take in the beautiful surroundings. A fireplace is a common amenity, superb for cozy evenings after a day of exploring the scenic Berkshire Mountains. Onsite parking is typically available, making it convenient for those traveling with their own vehicles. Additionally, many rentals include coffee and tea makers, ensuring guests can start their day with a warm beverage.
When is the best time to visit Great Barrington for a vacation rental?
The best time to visit Great Barrington for a vacation rental is during the bustling summer months from June to August. This peak season attracts a vibrant mix of travelers who come to enjoy the area's outdoor activities, cultural events, and the picturesque landscapes that the Berkshires have to offer. July, in particular, stands out as the most popular month, filled with lively events and an abundance of opportunities for hiking, biking, and exploring local art galleries.

During these summer months, visitors can expect warm temperatures ranging from the mid-60s to the mid-80s Fahrenheit, making it comfortable for outdoor adventures and sightseeing. Nearby attractions like the stunning Bash Bish Falls and the charming downtown area of Great Barrington provide ample opportunities for both relaxation and exploration.

For those looking to save a bit on accommodations, consider planning your trip in November. This month offers a quieter experience, where you can enjoy the serene beauty of the fall season as the leaves change colors and the crowds diminish. It's an excellent time for leisurely walks and enjoying the local shops without the hustle and bustle of peak tourist season.
How early should I book a Great Barrington vacation rental?
Book your Great Barrington vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Great Barrington, Massachusetts, United States of America?
In Great Barrington, visitors can enjoy a variety of attractions that showcase the area's natural beauty and cultural charm. The downtown area is vibrant, featuring unique shops, art galleries, and a selection of restaurants that reflect the local culinary scene. The Mahaiwe Performing Arts Center is a great venue, hosting live performances and events throughout the year.

For outdoor enthusiasts, nearby Monument Mountain offers hiking trails with stunning views of the surrounding Berkshires, making it a popular spot for both locals and tourists. The Housatonic River, which runs through the area, provides opportunities for kayaking and fishing.

Additionally, the nearby Berkshire Botanical Garden is a peaceful retreat, showcasing a diverse array of plants and gardens, ideal for a leisurely stroll.
Can I change or cancel my Great Barrington home rental booking on Vrbo?
To find Great Barrington vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Great Barrington vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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