Great Barrington vacation rentals

We found 635 vacation rentals — enter your dates for availability

Select from 97 homes, 16 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.
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Find out more about Great Barrington

Find out more about Great Barrington

Why visit Great Barrington

  1. Outdoor Adventure: Enjoy skiing, hiking, and exploring stunning national and state parks amidst breathtaking mountain views.
  2. Cultural Experiences: Discover the rich history and heritage through charming historic homes and local museums.
  3. Scenic Lakes: Relax by picturesque lakes perfect for fishing, kayaking, or picnicking with family and friends.
  4. Charming Neighborhoods: Stroll through welcoming neighborhoods filled with unique shops, restaurants, and beautiful architecture.
  5. Diverse Accommodations: Choose from a range of vacation rentals, from cozy condos to spacious homes, fitting every budget.

Popular types of accommodation in Great Barrington

Discover the charm of Great Barrington with our diverse vacation rentals. Whether you’re seeking budget-friendly apartments or a cozy home with a screened-in porch, there’s something for everyone. Popular options include condos, apart-hotels, and whole homes tailored to your needs. Explore great Barrington’s hidden gems and enjoy a relaxing getaway in the heart of the Berkshires!

  • Condos: The top choice for visitors in Great Barrington, offering modern amenities and a comfortable stay in a community setting.
  • Apartments: A close second, these self-contained units provide a home-like atmosphere with easy access to the town.
  • Houses: Ideal for families or groups, these homes provide space and privacy for a memorable getaway.
  • Cottages: Quaint and cozy, these charming abodes offer a delightful retreat in nature.
  • Cabins: Perfect for an outdoor experience, these rustic lodgings are great for those seeking adventure.**

Top attractions in Great Barrington

Great Barrington, Massachusetts, offers a fantastic blend of outdoor adventure and cultural experiences. Ideal for ski enthusiasts and sports lovers, the area features attractions such as national and state parks, scenic lakes, and historic houses. Travelers can enjoy various activities while soaking in the breathtaking views and exploring the local heritage. Don't miss the chance to admire the charming architecture of the historic homes in the area!

  1. National Shrine of the Divine Mercy: Located 7 miles from Great Barrington, this serene shrine offers a peaceful atmosphere for reflection and prayer, surrounded by beautiful gardens and religious art that enhance its spiritual culture.
  2. Norman Rockwell Museum: Situated 6 miles away, this museum features renowned American illustrator Norman Rockwell's work, showcasing his iconic paintings that capture everyday life and culture, making it a must-visit for art lovers.
  3. Lake Buel: Right in Great Barrington, this picturesque lake is perfect for romantic strolls, beach activities, and enjoying stunning outdoor scenery, providing a tranquil escape for visitors.

Things to do recommended for couples

Great Barrington offers a perfect romantic getaway for couples. Enjoy skiing at Ski Butternut, savor exquisite wines at Les Trois Emme Winery, and experience live performances at Tanglewood Music Center. These activities create unforgettable memories in a charming atmosphere.

Things to do recommended for families

Your family can enjoy a day at Lake Mansfield Park, perfect for relaxation and outdoor fun. Take a short drive to Tyringham Cobble or Goose Pond Reservation for more recreational activities, all set in beautiful surroundings that promote wellness and relaxation.

Things to do recommended for groups

Groups visiting Great Barrington can enjoy a scenic hike along the Housatonic River Walk, experience captivating performances at the Mahaiwe Performing Arts Center, and shop at the Lee Premium Outlets, just a short drive away for a fun day of family-friendly entertainment.

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

If you're traveling with a group, family, or pets, or planning an extended stay, be sure to prioritize your preferences when filtering options. Here are some helpful booking tips for Vrbo.

  • Traveling to Great Barrington with a group: Think about how many bedrooms you'll require, as well as additional features like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily refine your search for these options and more on Vrbo.
  • Traveling to Great Barrington with young kids: Traveling with young kids can present some challenges. It’s important to prioritize their comfort and safety, along with ensuring access to suitable amenities like a private swimming pool. Additionally, considering how close you are to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Great Barrington: For many families, a vacation wouldn't be the same without their furry companions. If you can relate to this, explore Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that all members of your family feel comfortable and at home.
  • Planning for a long term stay visiting Great Barrington: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search for the perfect getaway.

Where to stay in Great Barrington

Great Barrington, nestled in the scenic Southern Berkshires of Berkshire County, Massachusetts, offers a perfect blend of adventure and relaxation. Explore its family-friendly atmosphere, rich history, and romantic settings while enjoying stunning mountain views. Whether you're skiing down the slopes or strolling through charming neighborhoods, you'll find a welcoming community and a variety of activities to make your vacation unforgettable.

  • Lenox: Located 12 miles from Great Barrington, Lenox is a charming town known for its vibrant arts scene and romantic ambiance. This picturesque area offers a wealth of entertainment options, including live music concerts and theatrical performances. Outdoor enthusiasts can enjoy skiing in the nearby mountains during winter, while the tranquil lakes and parks provide a perfect backdrop for family outings. Lenox is also home to the renowned Tanglewood Music Center, where visitors can experience world-class performances in a stunning outdoor setting.
  • Hudson: Situated 22 miles away from Great Barrington, Hudson is a thriving city that attracts adventure seekers and nature lovers alike. Known for its stunning scenery, Hudson offers numerous outdoor activities, including skiing at nearby resorts and exploring the beautiful lakes and parks in the region. The city features a lively downtown area with unique shops and restaurants, making it a great spot to unwind after a day of adventure. Hudson's picturesque views and vibrant community make it an appealing destination for those looking to connect with nature.
  • Stockbridge: Just 7 miles from Great Barrington, Stockbridge is a delightful town steeped in history and culture. It offers visitors a romantic setting with its charming streets and cultural attractions. The town is famous for its art scene, with galleries and theaters showcasing local talent. Outdoor enthusiasts can engage in skiing at nearby ski fields, while the serene lakes and historical monuments provide plenty of opportunities for exploration. Stockbridge is also home to the iconic Norman Rockwell Museum, making it a must-see for art lovers.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January23.2°F (-4.9°C)Light RainMostly CloudyAverageSlightly High
February24.8°F (-4.0°C)Light RainMostly CloudyAverageSlightly High
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 HighAverage
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 LowAverage
December29.7°F (-1.3°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate significantly. Plus, opting for a longer stay can often lead to substantial savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to narrow down your search by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your booking. It truly benefits you to take on the planning role! When you join our travel rewards program, One Key, you can immediately access exclusive member savings and accumulate OneKeyCash™ on eligible reservations. Sign up today and begin enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your upcoming adventures, pick up where you last stopped, or manage your travel arrangements. You can easily access the properties you've saved or booked, now categorized into Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

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)
  • Kennedy Park (13.4 mi / 21.6 km)
  • Harney and Sons Tea Tasting Room (15.4 mi / 24.9 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?
Among the most sought-after neighborhoods for a Great Barrington vacation home is Egremont. When you book your Vrbo vacation property, you can look forward to having the whole place to yourself. This means you don’t have to share it with anybody apart from your favorite people.
What is the most popular type of vacation rental accommodation in Great Barrington?
Apartments are the most popular type of vacation rental in Great Barrington, according to our data. Even if you’ve got something different in mind, Vrbo has properties in many sizes and shapes. Browse our many options to find your perfect fit.
How much does it cost to rent a vacation rental in Great Barrington?
Property type, season and length of stay are some things that can influence the price of a vacation home. Simply click on your travel dates to find your dream escape. From homey country cottages to expansive villas, all Vrbo vacation rentals provide incredible value.
How much does it cost to rent a beach house in Great Barrington?
Prices for beach houses in Great Barrington can vary depending on the type and size of the property and when you plan to travel. Just enter your travel dates into Vrbo and the number of guests to view available options and prices. From there you can use the filters to refine your search results by amenities, ratings, nearby activities and more.
Are there pet-friendly vacation rentals in Great Barrington?
Yes. You can pick from 121 vacation rentals that allow pets in Great Barrington. Plenty of our pet-friendly vacation rentals come with an outdoor area for your furry pal to have fun in, complimentary treats, doggie beds and proximity to parks or green space. Apply the “Pets allowed” filter to find a pad that’ll set tails wagging on Vrbo.
Can I rent a house with a pool in Great Barrington?
Tick the “pool” box in our filter tool and choose from 22 houses with private pools in Great Barrington on Vrbo. Gentle soak, ball games or noodle joust? Leisure time is up to you when your Vrbo vacation home comes with its own swimming pool.
What are popular rental amenities in Great Barrington?
A garden, a barbecue grill and a firepit head the list of most popular rental amenities in Great Barrington. Whether you plan to go as a party of one, with your significant other or as a family, Vrbo will help you find a vacation rental that matches your tastes with all the features you need.
Are there large group vacation rentals in Great Barrington?
Great Barrington has 29 vacation properties that can host 10 or more guests. These stays come with all the space you need to enjoy good times with your favorite people.
Are there vacation rentals in Great Barrington that welcome kids?
With 121 family-friendly vacation properties available in Great Barrington, there’s never been a better time to introduce the little ones to the thrills of travel. Just click on our “Properties good for families” filter box to browse stays that come with conveniences ideal for traveling families, like multiple bedrooms, outdoor spaces, entertainment areas and hot tubs.
What are the top attractions for families in Great Barrington?
Keep your kids entertained at these leading family-friendly attractions in Great Barrington:

  • Ski Butternut
  • Housatonic River Walk
  • Mahaiwe Performing Arts Center

Are there one-bedroom vacation rentals in Great Barrington?
You’ll find 12 one-bedroom properties in Great Barrington to choose from. A one-bedroom vacation rental is a great choice if it’s only two of you or if you’re flying solo. Throw in more privacy, space and convenience compared to a standard hotel, and you’re bound to have a getaway to remember.
Can I find two-bedroom vacation rentals in Great Barrington?
Gather your family and enjoy peace, privacy and comfort in one of the 14 two-bedroom vacation homes Great Barrington has to offer.
Are there vacation rentals with WiFi in Great Barrington?
Great Barrington has 45 vacation rentals with WiFi, so you’ll be able to stay connected during your trip. Simply check the “WiFi” box in our handy search filter for a list of properties with this feature. From streaming TV shows with the family to sending emails, these Vrbo homes make it a breeze to get online.
How can I find vacation rentals with air conditioning in Great Barrington?
You’ll find 106 vacation homes with air conditioning in Great Barrington offering that gentle, cool breeze and extra touch of comfort. Simply enter your preferred dates of travel and then make use of our filters to help you locate stays with air conditioning.
How old do you have to be to rent a vacation rental in Great Barrington?
The minimum age is typically 16, 18 or 21. It can vary from property to property on Vrbo, so look at the rules of your preferred Great Barrington stay before you book.
How long can I rent a vacation rental in Great Barrington for?
The length of time you can rent a vacation rental in Great Barrington depends on the property. Just enter your selected travel dates to see a list of options offering extended stays. With lots of features like washing machines and kitchens, as well as some offering weekly or monthly discounts, you’re sure to discover a perfect place to call your home away from home in Great Barrington.
Does Vrbo offer discounts for vacation homes in Great Barrington?
In Great Barrington, you’ll find some fabulous discounts and bargains for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you’re after a weekend getaway or a few weeks away, we’ve got a variety of options to suit your needs and budget.

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