Great Barrington holiday rentals

We found 640 holiday rentals — enter your dates for availability

Select from 92 homes, 17 cottages and other holiday rentals in Great Barrington to find one that's 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.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

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)
  • Wyndhurst Golf & Club (11.3 mi / 18.1 km)
  • Kennedy Park (13.4 mi / 21.6 km)
  • Harney and Sons Tea Tasting Room (15.4 mi / 24.9 km)
  • Bousquet Ski Area (15.7 mi / 25.3 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 Stayz 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, Stayz 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 Stayz. 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 Stayz.
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 Stayz, 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 Stayz 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, Stayz’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 Stayz 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 Stayz. 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 Stayz, 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.

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