Discover a selection of 500 vacation rentals in Great Barrington, MA that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $240 per night, and houses and condos are popular options for a stay in Great Barrington. Either way, you'll find a rental for everyone's needs.
AsyncDestinationUrgency
Top rated rentals — Great Barrington
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
Destination guide

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.

Things to do

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)
  • Cranwell Golf Club (11.3 mi / 18.1 km)
  • Otis Ridge (13.4 mi / 21.5 km)
  • Furnace Brook Winery at Hilltop Orchards (13.8 mi / 22.2 km)
  • Bousquet Ski Area (15.7 mi / 25.3 km)
Weather

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 December, January, February or March, when snowfall averages 12 inches and temperatures average 27°F.

Natural features

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)
  • Beartown State Forest (5.4 mi / 8.7 km)
  • Naumkeag (6.9 mi / 11.1 km)
  • Bash Bish Falls State Park (8.9 mi / 14.3 km)
  • The Mount (10.5 mi / 16.8 km)
  • Taconic State Park (11.7 mi / 18.8 km)
How to get there

Transportation options to and around Great Barrington

The nearest airport is in Albany Intl. Airport (ALB), located 44.3 mi (71.3 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Bradley Intl. Airport (BDL), which is 39.3 mi (63.2 km) away.

What are the top vacation rentals in or near Great Barrington?

Whether you're after an intimate retreat for you and your special someone or someplace spacious to fit all your friends, you'll find some top vacation rentals in and around Great Barrington. Here are a couple to get you thinking:

  • "Close To Skiing Beautiful +family Friendly" is a favorite with guests. Around 7 miles from Great Barrington, it has 4 bedrooms and loads of useful amenities, including pet-friendly services and a dining table.
  • Alternatively, unpack your bags at "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi". Located around 16 miles from the heart of Great Barrington, it has 4 bedrooms and features a smart TV and a games room.

For even more great options, use the search bar at the top of the page to find the perfect Great Barrington vacation rental for you.

Can I find log cabins to rent in or near Great Barrington?

Choose your favorite log cabin from the many dotted in or near Great Barrington and you'll soon be inside your wooden hideaway, coffee in hand, unwinding next to a glowing fire. But adventure is right outside your door too. These cabins promise the perfect blend of fun and comfort:

  • "Cozy Log Cabin Adjacent To Beartown Forest": This is the perfect base to enjoy some of the exciting outdoor activities this area has to offer, including golf and snowmobiling.
  • "Water Front Log Cabin Next To Tanglewood": Spend your break enjoying all the creature comforts at this escape. When it's time to get outdoors, snowboarding and skiing will get your blood flowing.

What are the top-rated vacation rentals for weekend getaways in or near Great Barrington?

There's nothing better than a quick escape to dust away the cobwebs. Pack your overnight bag and take a load off at one of these weekend getaways in and around Great Barrington:

  • "Elterwater - - Your Lakefront Oasis" is a popular option around 4 miles south of central Great Barrington. There's no need to go far to find an unforgettable experience around this property. Get out and visit Blandford Ski Area and C.M. Gardner State Park. Activities like horse riding and cycling will add a nice touch to your quick break.
  • Alternatively, enjoy some downtime at "Swiss Chalet Style Timber Frame Home In Berkshires With All Modern Conveniences". Approximately 25 miles northeast of Great Barrington, activities around here include cycling and mountain biking. Prefer sightseeing? Don't miss Western Gateway Heritage State Park and Pleasant Valley Wilderness Sanctuary.

Can I find studio apartments for rent in and around Great Barrington?

Typically small, affordable and well located, it's not difficult to fall for the appeal of a studio apartment. Escape to one of these options and get acquainted with Great Barrington up close:

  • Throw your suitcase down at "The Clearing - Quiet - Close To Nature". Amenities including a pool and beach towels will help you feel right at home here.
  • "Cabin - A - Frame In Sherwood Forest" is another top choice. Make yourself comfy and take advantage of shopping, a fridge and more.

When you're ready to step foot outside your studio apartment and go exploring, there's plenty to entertain you around Great Barrington. Love cultural attractions? Don't miss Museum of American Bird Art at Mass Audubon and Merrimack Repertory Theater.

Can I find short term rentals in or near Great Barrington?

Just because you only have two or three days up your sleeve doesn't mean you need to spend it in a boring hotel. Take off on vacation but still have the home comforts you need at one of these short-term rentals in or around Great Barrington:

  • "Swiss Chalet Style Timber Frame Home In Berkshires With All Modern Conveniences" is close to the center of Great Barrington, which means there are plenty of things to do and see. Tick off well-known attractions like Walden Pond and Louisa May Alcott's Orchard House when you're not kicking back in your cozy rental.
  • Sleep, relax and explore from "Unique People And Pet - Welcoming Country Haven", another good option. Old Manse and Concord Visitors Center should be on your to-do list when you're ready to sightsee.

What are the best romantic weekend getaways in or near Great Barrington?

Forget chocolates and flowers. Sometimes all you need is a weekend away, just you and your sweetie. At Vrbo, we've got romantic getaways in and around Great Barrington that would make even old Cupid envious. Here are some we think you'll adore:

  • Around 7 miles from Great Barrington, "Close To Skiing Beautiful +family Friendly" is an ideal place for doting couples. Skiing facilities and a fireplace are among the many amenities here.
  • Another option where you can spend a few idyllic days together is "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi". Located around 16 miles from Great Barrington, shopping facilities and a balcony add to the ambiance here.

What are the best houses for rent with a pool in or near Great Barrington?

Nothing spells fun like a pool. Grab your inflatable flamingo and browse these houses in or near Great Barrington that feature this added bonus:

  • Get into vacay mode at "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi", where your highest priority will be pool time. Amenities including a dining table and a balcony help make this retreat a favorite with guests.
  • "General Williams Estate House Lenox" is the type of place you go to escape the everyday and appreciate your surroundings, starting with its awesome pool. A separate dining area and a TV are also on hand to make your visit comfortable and convenient.

Don't know what to pack for your Great Barrington break? This leading destination has a humid continental climate. During the summer months, you can expect average temperatures ranging from 55 ºF to 80 ºF. Look up our range of Great Barrington vacation rentals by using the search bar at the top of the page. Simply adjust the filters to get more ideas about where to stay.

What are the best large family vacation rentals in or near Great Barrington?

It's always more fun to share those memorable moments with the people you love the most. Whether you're organizing a family get-together or spending time with good friends, we'll have a large vacation rental that's just right for you. Here are two of our best in and around Great Barrington:

  • Get your nearest and dearest together at "88 Acres Of Beauty In The Berkshires", which has 4 bedrooms that sleep up to 9 guests. This retreat is around 7 miles to the southwest of Great Barrington and comes with amenities such as a fridge and nearby birdwatching activities.
  • Another top choice is "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi". This large rental is 16 miles east of Great Barrington and features childrens activities, a dishwasher and more. With 4 bedrooms accommodating up to 10 people, don't worry about leaving anyone off your guest list.

When you're ready to get out and explore, there are loads of family-friendly attractions nearby to keep everyone happy and entertained. New England Aquarium, Newbury Street and CoCo Key Water Resort - Boston should be on your itinerary.

Can I find family cabin rentals in or near Great Barrington?

Take a break with the kids in a family cabin rental in or near Great Barrington and get ready to make some amazing new memories together. Here's just a taste of what we've got:

  • "Cabin - A - Frame In Sherwood Forest" - Around 17 miles northeast of the center of Great Barrington, this family-friendly getaway comes with a separate dining area and a barbecue grill.
  • "Quiet Comfortable Cabin 5 Min. Walk To Swimming And Boating" - Rally the troops and spend a few days or more at this inviting stay, which is around 16 miles to the east of Great Barrington. You'll have access to beach sun loungers, childrens activities and much more.

For more options, use the search bar at the top of the page and adjust the filters to find the Great Barrington vacation rental that's perfect for your needs.

What are the best large houses to rent with indoor pools in or near Great Barrington?

Add an extra touch of luxury to your getaway by booking somewhere that has a private indoor pool. These amazing large houses in or near Great Barrington have a swimming space that's just for you, as well as loads of room for whoever is lucky enough to be coming along:

  • Book a stay at "Monument Mountain Lodge" and while away your days poolside. This sprawling getaway has 6 bedrooms sleeping up to 12 guests and a range of other excellent amenities. A fireplace and mountain views are among them.
  • In addition to its inviting indoor pool, "Equipped Villa With Access To Pools" comes with a swimming pool and a garden. It has 3 bedrooms that can cater for up to 8 people, so you can bring your entire gang along.

If you'd like to see even more options, use the search bar at the top of the page and adjust the filters to find the Great Barrington vacation rental that's perfect for your needs.