Great Barrington holiday lettings

We found 662 holiday rentals — enter your dates for availability

Discover a selection of 94 homes, 10 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:3 Oct - 10 Oct
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Why visit Great Barrington

  • Adventure sports: Great Barrington is renowned for skiing and a variety of outdoor activities, perfect for thrill-seekers.
  • Historic exploration: Discover charming historic houses and local shrines that reflect the area's rich heritage.
  • Stunning scenery: Enjoy breathtaking views and tranquil spots for relaxation amidst beautiful landscapes.
  • Charming local vibe: Experience lively local eateries and shops, offering a warm community atmosphere.
  • Varied accommodation: Choose from a range of holiday rentals, including cosy cottages and modern condos, to suit any preference.

Popular types of accommodation in Great Barrington

If you're considering a getaway to Great Barrington, you're in for a treat! This charming destination offers a variety of holiday rentals to suit your needs. The most popular options include houses, cosy cottages, and modern condos. Whether you're seeking spacious bedroom rentals or properties with extra amenities, you'll find the perfect holiday rental in Great Barrington to create lasting memories.

  • Houses: The top choice for visitors to Great Barrington, offering spacious and comfortable settings ideal for families or groups.
  • Condos: A popular alternative, these self-contained units provide a blend of convenience and modern amenities.
  • Cottages: Quaint and charming, cottages offer a delightful retreat amidst scenic surroundings.
  • Apartments: Perfect for a more urban feel, apartments provide a home-away-from-home experience.
  • Cabins: Embrace the outdoors with rustic cabins that are perfect for nature enthusiasts.**

Top attractions in and around Great Barrington

Great Barrington is an ideal destination for skiing and adventure sports, offering a variety of attractions for visitors. You can explore historic houses, national and state parks, and local shrines, catering to those seeking outdoor activities, cultural experiences, and thrilling adventures. Whether you're keen on skiing or immersing yourself in the area's rich history, Great Barrington has something for everyone to enjoy.

  • National Shrine of the Divine Mercy: A serene and spiritually enriching site, this shrine offers a peaceful atmosphere and beautiful architecture, perfect for contemplation and prayer, set in a picturesque landscape just 4.3km from Great Barrington.
  • Lake Buel: This idyllic lake features a charming beach and stunning scenery, ideal for outdoor activities and romantic picnics, right within Great Barrington.
  • Housatonic River: A scenic river that provides a backdrop for outdoor adventures such as kayaking and fishing, located a mere 62m from the town, enhancing your natural exploration.

Things to do recommended for couples

For a romantic getaway in Great Barrington, indulge in a day at Ski Butternut for some exhilarating skiing, followed by enchanting melodies at Tanglewood Music Center just 6.8km away. Cap off your adventure with a delightful tasting at Les Trois Emme Winery, perfect for couples seeking romance.

Things to do recommended for families

Your family will love exploring Lake Mansfield Park in Great Barrington, a lovely spot for relaxation and wellness. For a bit of adventure, head to Tyringham Cobble, just 5.0km away, or discover the serene Goose Pond Reservation, located 6.8km from town.

Things to do recommended for groups

Groups visiting Great Barrington can enjoy a scenic hike along the Housatonic River Walk, experience culture and entertainment at the Mahaiwe Performing Arts Center, and indulge in shopping at the Lee Premium Outlets, located a short drive away, offering a delightful mix of retail and leisure.

Booking with Vrbo is a breeze

Are you hoping to save on your next holiday? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, booking a longer stay can lead to considerable savings. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Where to stay near Great Barrington

Great Barrington, Massachusetts, offers a delightful blend of adventure and relaxation, perfect for a memorable holiday. With its stunning scenery and vibrant atmosphere, you can enjoy outdoor seating in lively local spots. Explore charming nearby towns and indulge in family-friendly activities, or find a romantic nook to unwind. It's an ideal location for skiing and sports, making it a fantastic getaway for those seeking both thrill and tranquillity.

  • Lenox: Situated 7.5km from Great Barrington, Lenox is renowned for its vibrant entertainment scene, making it an ideal destination for a romantic getaway or family adventure. Visitors can enjoy a variety of activities, including music concerts and theatre performances, as well as skiing during the winter months. The picturesque landscape features beautiful lakes and mountains, providing the perfect backdrop for outdoor pursuits. Additionally, the town hosts an array of event venues, making it a popular spot for conferences and gatherings.
  • The Berkshires: Located 6.8km away from Great Barrington, The Berkshires is a haven for outdoor enthusiasts seeking adventure and stunning scenery. The area is famous for its excellent skiing opportunities, with numerous ski fields and resorts to explore. Visitors can revel in the natural beauty of the lakes and mountains while engaging in various outdoor activities. The Berkshires also boasts charming communities and local events, ensuring a memorable experience for all who venture into this enchanting region.
  • Stockbridge: Just 4.3km from Great Barrington, Stockbridge is a charming town steeped in culture and history. It offers a delightful blend of romantic experiences and entertainment, with a thriving arts scene featuring music concerts and theatre performances. Outdoor activities are abundant, particularly around its scenic lakes and notable landmarks, including monuments and shrines. Stockbridge is the perfect place to immerse yourself in local culture while enjoying the stunning natural surroundings.

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 HighSlightly High
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 LowAverage
December29.7°F (-1.3°C)Light RainMostly CloudySlightly LowSlightly High

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

When planning your trip, whether you're journeying with a group, enjoying a family getaway, bringing along your pets, or seeking extended stays, it's essential to refine your search according to your key priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Great Barrington with a group: Think about how many bedrooms you'll require, along with additional features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all these options and 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 fulfilling without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. The majority of these pet-friendly accommodations offer feeding bowls and beds, ensuring that all members of the family feel at home.
  • Planning for a long term stay visiting Great Barrington: If you're seeking holiday rentals with offers for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include features like a parking space, a well-equipped kitchen, or even a private pool in your search.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient space to plan new holidays, pick up from where you last left off, or review and organise your travel arrangements. Any properties you've previously saved or booked can now be easily located under Potential, Upcoming, or Current Trips. To start using Trip Boards, please visit: https://www.vrbo.com/en-gb/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)
  • 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 rental?
One of the more in-demand destinations to choose your Vrbo holiday rental 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 rental accommodation in Great Barrington?
Houses are the most popular style of holiday rental in Great Barrington, according to our data. Even if you've got a different idea in mind, Vrbo 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 rental in Great Barrington?
Different things can determine what you'll pay for your holiday rental 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 rental. Put in your Great Barrington travel dates to see your options on Vrbo. Can't live without a hot tub? Use the filters to pick the features and amenities you want.
Are there pet-friendly holiday rentals 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 rentals and find the pawfect pad on Vrbo.
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 Vrbo, then check the "pool" filter to find the ideal place for a splashing good time!
What are popular rental amenities in Great Barrington?
When it comes to rental amenities that guests are searching for in Great Barrington, a swimming pool, an electric car charging station and nearby museums rank the highest. With Vrbo 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 rentals 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 rentals 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 rentals in Great Barrington?
Yes, you can pick from three one-bedroom rentals in Great Barrington. Whether you want a cosy cottage or an upmarket condo, Vrbo's one-bedroom rentals 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 rentals 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 rentals with WiFi in Great Barrington?
Great Barrington has 12 holiday rentals 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 Vrbo homes make it easy to get online.
How can I find holiday rentals with air conditioning in Great Barrington?
Work out your travel dates and then use our filter tool to see holiday rentals with ac in Great Barrington on Vrbo. 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 rental in Great Barrington?
Age restrictions can differ across properties on Vrbo, so look at the rules of the holiday rental in Great Barrington you're interested in. But normally, it's 16, 18 or 21.
How long can I rent a holiday rental in Great Barrington for?
The length of time you can rent a holiday rental 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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