Great Barrington vacation rentals

We found 671 vacation rentals — enter your dates for availability

Select from 96 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:Mar 27 - Apr 3

Image gallery for Waterfront Cottage 10 Min From Great Barrington

Property grounds
10 out of 10, Exceptional, (99 reviews)
Exceptional
(99 reviews)

Waterfront Cottage 10 Min From Great Barrington

New Marlborough

8% off
Price is $323
$2,264 for 7 nights
All fees included
Waterfront Cottage 10 Min From Great Barrington

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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)
  • Wood's Pond (12 mi / 19.3 km)
  • Otis Ridge (13.4 mi / 21.5 km)
  • Kennedy Park (13.4 mi / 21.6 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 when booking a vacation rental?
When considering a vacation rental in Great Barrington, Massachusetts, a popular area to stay is the downtown district. This vibrant neighborhood is not only charming but also offers a variety of shops, restaurants, and cultural experiences, making it an ideal base for exploring the town. You'll find a rich selection of properties, from cozy apartments to larger homes, suiting different group sizes and preferences.

In downtown Great Barrington, you'll be just a short stroll away from the Mahaiwe Performing Arts Center, which hosts a range of performances and events throughout the year. Additionally, the nearby Lake Mansfield Park provides a beautiful natural retreat for outdoor enthusiasts, offering opportunities for swimming, hiking, and picnicking.

Another appealing area is the Housatonic neighborhood, located just north of downtown. This area features a more residential feel while still being close to the action.
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 near Great Barrington, Massachusetts, travelers should focus on the nearby areas of Butternut Basin and Catamount Mountain Resort. In the Great Barrington area, visitors can find a variety of vacation rentals, including cozy cabins and modern chalets that cater to different group sizes. Many of these properties offer amenities such as fully equipped kitchens, fireplaces, and outdoor spaces for enjoying the beautiful natural surroundings.

In the vicinity of Butternut Basin, properties often provide easy access to the ski slopes, with some rentals featuring ski-in/ski-out capabilities. Look for accommodations that include hot tubs or saunas, superb for relaxing after a day on the mountain. The charming town of Great Barrington itself offers a vibrant atmosphere, with local shops, restaurants, and cultural activities, enhancing the overall experience for travelers.

Additionally, the nearby Catamount Mountain Resort area presents options for those looking for a slightly different ski experience. Rentals in this region can include rustic lodges and upscale condos, many of which come with amenities like game rooms or communal fire pits, fostering a friendly, communal atmosphere. The surrounding landscapes also provide opportunities for winter hiking and snowshoeing, making this a well-rounded destination for winter sports enthusiasts.
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 81 available throughout the area. These homes typically feature multiple bedrooms, spacious living areas, fully equipped kitchens, and often outdoor spaces like decks or patios superb for enjoying the scenic views of the Berkshire Mountains. Additionally, there are around 15 charming cottages, which provide a cozy and rustic feel, ideal for couples or small families. While there are several apartments and cabins available, the emphasis remains on the larger vacation houses that cater to groups seeking comfort and convenience during their stay.
Are there any family house rentals in Great Barrington?
In Great Barrington, Massachusetts, families will find a variety of vacation rentals—approximately 83 options available throughout the area. The town is known for its picturesque landscapes and proximity to outdoor activities, making it an ideal destination for families seeking adventure and relaxation. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces that are superb for children to play.

Neighborhoods like the historic downtown area provide easy access to local attractions, while nearby parks and nature reserves offer opportunities for hiking, picnicking, and exploring the beautiful surroundings. Amenities such as Wi-Fi, air conditioning, and laundry facilities are commonly included, ensuring a comfortable stay for visitors. See all family-friendly rentals in Great Barrington.
Can I rent a vacation home with a pool or hot tub in Great Barrington?
In Great Barrington, there are several vacation homes available for rent that feature pools and hot tubs, with around 19 options to choose from. This picturesque town in the Berkshires is known for its beautiful landscapes and outdoor activities. Travelers can find properties in various neighborhoods, including the charming downtown area and the more secluded settings near the mountains.

Many of these rentals come equipped with private pools, hot tubs, and spacious outdoor areas superb for relaxation and family gatherings. Inside, you can expect fully equipped kitchens, cozy living spaces, and amenities such as Wi-Fi and air conditioning to ensure a comfortable stay. 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, there are numerous pet-friendly house rentals available, offering a variety of amenities to ensure a comfortable stay for travelers with pets. Many of these rentals feature spacious layouts, fully equipped kitchens, and outdoor areas where pets can roam freely. Some properties even come with fenced yards, making them ideal for those traveling with dogs.

The town itself is surrounded by beautiful landscapes, providing plenty of opportunities for outdoor activities, including hiking and walking trails. Nearby parks, such as the Monument Mountain Reservation, offer scenic views and pet-friendly paths for exploration. Additionally, Great Barrington boasts a charming downtown area with pet-friendly cafes and shops, ideal for visitors traveling with 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, travelers will find a wealth of remote work vacation rentals available, with around 101 options to choose from. This charming town, known for its picturesque landscapes and vibrant arts scene, provides a conducive environment for remote work. Many properties come equipped with amenities designed for productivity, such as dedicated office spaces, high-speed Wi-Fi, comfortable desks and chairs, and sometimes even additional features like computer monitors and safe storage options.

Staying in Great Barrington allows guests to enjoy the local culture, with attractions such as the Mahaiwe Performing Arts Center and the beautiful hiking trails of the nearby Berkshire Mountains. The town also offers a variety of dining options and local shops, making it easy to take breaks and explore during work hours. 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, vacation rentals commonly offer a range of amenities that enhance the guest experience. Most properties include WiFi, allowing travelers to stay connected, and kitchens equipped for preparing meals, which is ideal for those who prefer dining in. Additionally, many rentals feature patios, providing outdoor space to relax and enjoy the beautiful surroundings. Coffee and tea makers are typically available, suiting morning routines, and many rooms include blenders for preparing smoothies or other beverages.
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 peak summer season, which runs from June to August. This vibrant period attracts a mix of adventure seekers and relaxation enthusiasts who flock to the area to enjoy its picturesque landscapes and rich cultural offerings. July, in particular, is the most popular month, providing travelers with an array of outdoor activities, from hiking in the nearby Berkshire Mountains to exploring local art galleries and enjoying lively events.

During these summer months, visitors can relish in comfortable weather, typically ranging from the mid-60s to the mid-80s Fahrenheit. This climate is ideal for outdoor activities like kayaking on Lake Mahkeenac or strolling through the charming downtown area, where boutique shops and farm-to-table restaurants await. The ambiance is lively, with many festivals and farmers' markets adding to the local charm.

For those looking for a more budget-friendly option, consider visiting in November. This month offers a quieter experience, with fewer crowds and the chance to enjoy the serene beauty of the fall landscape.
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?
In Great Barrington, visitors can enjoy a variety of attractions that showcase the area's natural beauty and cultural offerings. The town is known for its charming downtown area, where you'll find local shops, art galleries, and restaurants that highlight the region's farm-to-table cuisine. Nearby, the picturesque Butternut Basin offers year-round outdoor activities, including hiking in the warmer months and skiing in the winter.

For those interested in the arts, the Mahaiwe Performing Arts Center hosts a range of performances, from live music to theater, adding to the cultural vibrancy of the area. Just a short drive away, the scenic landscapes of the Berkshires provide ample opportunities for outdoor enthusiasts, with hiking trails in places like the Appalachian Trail and the stunning views from Monument Mountain.
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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