Great Barrington holiday homes

We found 685 holiday rentals — enter your dates for availability
Discover a selection of 97 homes, 12 apartments and other holiday rentals in Great Barrington that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll find the amenities that you need and want, including Wi-Fi and parking. Whatever you're looking for, you'll be sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Great Barrington

Showing deals for:6 Nov - 13 Nov

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Why visit Great Barrington

  • Outdoor adventures: Enjoy skiing, adventure sports and exploring scenic nature reserves within Great Barrington.
  • Cultural charm: Experience the vibrant local community through festive events and the Great Barrington Public Theater.
  • Historic allure: Discover historic houses and national parks that showcase the town’s rich past.
  • Quaint downtown: Wander through unique shops and eateries in a lively downtown setting.
  • Family and romance: Find family-friendly activities and romantic spots for a memorable getaway.

Top attractions near Great Barrington

Great Barrington, Massachusetts, is a charming destination perfect for outdoor enthusiasts and culture seekers alike. Visitors can enjoy skiing, adventure sports, and explore beautiful nature reserves, historic houses, and national parks. The local community hosts various holiday events and activities, making it an ideal spot for a festive getaway. Don't miss the Great Barrington Public Theater, which adds a vibrant cultural touch to your holiday experience in this picturesque town.

  • National Shrine of the Divine Mercy: A culturally rich shrine located 11km away from Great Barrington, offering a spiritual retreat and a glimpse into local religious artistry.
  • The Mount: A historic house 16km away from Great Barrington, providing insight into local heritage and the arts, set in a serene environment.
  • Bash Bish Falls State Park: A national state park 14km away, perfect for outdoor enthusiasts seeking adventure and breathtaking scenery.

Things to do recommended for couples

Discover romance in Great Barrington, where you can enjoy scenic strolls and charming local eateries. Embrace the day with a couple’s picnic in nearby parks and an intimate dinner in cosy restaurants, perfect for a memorable Kiwi getaway.

Things to do recommended for families

Families in Great Barrington can enjoy interactive museum exhibits and scenic walks, perfect for kids. Discover local flavours and experience outdoor adventures, creating memories that last a lifetime.

Things to do recommended for groups

Groups visiting Great Barrington can experience thrilling motorsport at Lime Rock Park, just 29km away, or tackle the adventurous zipline ropes course at Catamount Aerial Adventure Park, located 10km from town. Both offer fantastic outdoor vibes for a memorable group holiday.

*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

When you're planning a trip—whether with a group, family, pets, or for an extended stay—be sure to use the appropriate filters to match your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Great Barrington with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Great Barrington with young kids: Travelling with young children can be quite demanding. It’s essential to prioritise 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 family-friendly attractions.
  • Taking your pets with you to Great Barrington: For many, a family holiday isn’t truly complete without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Great Barrington: If you’re in search of holiday rentals with great offers for stays of a month or more, you’ve come to the right spot. By using the appropriate filter, you can effortlessly locate 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 charming blend of adventure and relaxation. Explore the vibrant downtown full of unique shops and eateries, or immerse yourself in the stunning natural scenery surrounding the area. With opportunities for skiing and outdoor sports, as well as family-friendly events and romantic spots, Great Barrington is perfect for a memorable holiday experience. Don't miss out on seasonal festivities that showcase the local culture and community spirit.

  • Lenox: Lenox, a charming city located 19km from Great Barrington, offers an enticing blend of entertainment, romance and cultural experiences. Wander through venues hosting lively music concerts and theatre performances, and embrace the winter season with skiing adventures. The city is graced by scenic natural landmarks such as a serene lake and a majestic mountain, as well as a versatile event conference venue, making it a well-rounded destination for those seeking a mix of urban charm and nature’s beauty.
  • The Berkshires: Just 18km from Great Barrington, The Berkshires is a haven for travellers who appreciate outdoor pursuits, adventure and breathtaking scenery. The region boasts excellent skiing opportunities, with access to ski fields and resorts that cater to winter sports enthusiasts. Surrounded by picturesque landscapes, including a tranquil lake, a prominent mountain and an event conference venue, The Berkshires provides an ideal setting for exploring the great outdoors and partaking in thrilling activities.
  • Stockbridge: Stockbridge, a delightful city located 11km from Great Barrington, is perfect for those seeking a romantic and culturally rich escape. With a blend of entertainment-themed attractions such as music concerts and theatre, and the allure of winter sports at nearby ski fields, Stockbridge invites visitors to immerse themselves in its artistic and lively atmosphere. The area is also home to a scenic lake, a historic monument and a revered place of worship, offering a diverse range of attractions for every traveller.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January23.2°F (-4.9°C)Light RainMostly CloudyAverage
February24.8°F (-4.0°C)Light RainMostly CloudyAverage
March32.5°F (0.3°C)Light RainMostly CloudyAverage
April44.2°F (6.8°C)Light RainMostly CloudyAverage
May55.9°F (13.3°C)Light RainMostly SunnyAverage
June63.7°F (17.6°C)Light RainMostly SunnySlightly High
July69.8°F (21.0°C)Light RainMostly SunnySlightly High
August67.8°F (19.9°C)Light RainMostly SunnySlightly High
September60.8°F (16.0°C)Light RainMostly SunnyAverage
October49.8°F (9.9°C)Light RainMostly SunnySlightly Low
November37.8°F (3.2°C)Light RainMostly SunnySlightly Low
December29.7°F (-1.3°C)Light RainMostly CloudySlightly Low

Booking with Vrbo is a breeze

Looking to cut costs on your next adventure? Adjusting your travel dates could be a smart move since prices often fluctuate. Likewise, you might secure great savings by opting for a longer stay. To locate a Vrbo property that suits your budget, simply use our filters to sort by price, location, and holiday rental type.

Vrbo Trips: Planning made easy

Vrbo's clever Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or easily manage your travel arrangements. You can find the properties you've saved and booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

The lively city of Great Barrington awaits you

The area's live music and theatre scene are just some of the reasons to come on holiday to Great Barrington. Well known for its rock climbing, hiking and cafes, this scenic city won't disappoint. With a holiday 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

Are you looking for attractions to see during your stay? You'll be sure to enjoy Great Barrington for its hiking and skiing. Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Great Barrington a one-of-a-kind holiday spot. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Ski Butternut (2.3 mi / 3.7 km)
  • Catamount Ski Area (6.3 mi / 10.1 km)
  • Umpachene Falls Park (8.4 mi / 13.6 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)

Exploring the natural landscape of Great Barrington

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Great Barrington is a great place to get out in nature. These are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • 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

Travellers 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 18 cm and temperatures average -2°C.

Transport 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 centre. If you can't find a flight that's convenient for your trip, you might consider flying 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 holiday home?
One of the more in-demand destinations to choose your Bookabach holiday home in Great Barrington is Egremont. Set up home here and enjoy its big-ticket attractions, including Catamount Ski Area and Jug End State Reservatio.
What is the most popular type of holiday home accommodation in Great Barrington?
Houses are the most popular style of holiday home in Great Barrington, according to our data. Even if you've got a different idea in mind, Bookabach has properties in many shapes and sizes. Look through our options to find your perfect pad.
How much does it cost to rent a holiday home in Great Barrington?
Different things can determine what you'll pay for your holiday home in Great Barrington, like the type of property, season and length of stay. However, all our holiday homes have one thing in common — amazing value. Just enter your travel dates to find your ideal escape.
How much does it cost to rent a beach house in Great Barrington?
When you travel and the style and size of the property will influence how much you'll pay for your beachside holiday home. Put in your Great Barrington travel dates to see your options on Bookabach. Can't live without a hot tub? Use the filters to pick the features and amenities you want.
Are there pet-friendly holiday homes in Great Barrington?
With 39 properties that host four-legged guests, your happy hound can join in on your Great Barrington getaway. Use our filter tool to browse our pet-friendly holiday homes and find the pawfect pad on Bookabach.
Can I rent a house with a pool in Great Barrington?
Grab your swimsuit and pool noodle, because there are four houses with a private pool in Great Barrington. Kick back at one of these popular holiday homes and every day can be a pool day. Simply enter your dates into Bookabach, then check the "pool" filter to find the ideal place for a splashing good time!
What are popular home amenities in Great Barrington?
When it comes to home amenities that guests are searching for in Great Barrington, a swimming pool, an electric car charging station and nearby museums rank the highest. With Bookabach holiday homes, you'll discover options to suit your style and taste, whether you're going on a trip with your partner, your friends or even pets.
Are there large group holiday homes in Great Barrington?
Great Barrington has six holiday properties that can accommodate 10 or more guests. These stays come with the space and privacy you need to share good times with your favourite people.
Are there holiday homes in Great Barrington that welcome kids?
Bring the entire family together for an unforgettable adventure in Great Barrington at one of our 39 family-friendly holiday homes. Many of these stays come with conveniences that are ideally suited to trips with the kids, such as laundry facilities, extra bedrooms and outdoor spaces. Just check the "Properties good for families" filter and choose your favourite option.
What are the top attractions for families in Great Barrington?
Keep your kids busy at these fantastic family-friendly attractions in Great Barrington:

  • Umpachene Falls Park
  • Norman Rockwell Museum
  • Bash Bish Falls State Park

Are there one-bedroom holiday homes in Great Barrington?
Yes, you can pick from three one-bedroom homes in Great Barrington. Whether you want a cosy cottage or an upmarket condo, Bookabach's one-bedroom homes are ideal if you don't require lots of room. One of the best things about having your own place? You won't ever have to share your holiday with strangers.
Can I find two-bedroom holiday homes in Great Barrington?
Gather your loved ones and enjoy total privacy and comfort in one of the 10 two-bedroom holiday properties Great Barrington has to offer.
Are there holiday homes with WiFi in Great Barrington?
Great Barrington has 12 holiday homes with WiFi, so you'll be able to stay connected while you're away. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming TV shows with the family to checking emails, these Bookabach homes make it easy to get online.
How can I find holiday homes with air conditioning in Great Barrington?
Work out your travel dates and then use our filter tool to see holiday homes with ac in Great Barrington on Bookabach. With 34 air-conditioned properties to choose from here, you can enjoy a comfy and cool stay.
How old do you have to be to rent a holiday home in Great Barrington?
Age restrictions can differ across properties on Bookabach, so look at the rules of the holiday home in Great Barrington you're interested in. But normally, it's 16, 18 or 21.
How long can I rent a holiday home in Great Barrington for?
The length of time you can rent a holiday home in Great Barrington depends on the property. Just enter your selected dates to view a list of options offering extended stays. With plenty of features like washing machines and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to discover a terrific place to call your home away from home in Great Barrington.