Great Barrington vacation rentals

We found 670 vacation rentals — enter your dates for availability

Select from 95 homes, 14 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.

Vacation rentals with weekly discounts - Great Barrington

Showing deals for:Feb 13 - Feb 20

Image gallery for Little House in the Woods by Evergreen Home

Welcome to the Little House!
10 out of 10, Exceptional, (34 reviews)
Exceptional
(34 reviews)

Little House in the Woods by Evergreen Home

Sheffield, MA

15% off
Price is CA $382
CA $3,894 total
includes taxes & fees
Little House in the Woods by Evergreen Home

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Find out more about Great Barrington

Why visit Great Barrington

  • Outdoor adventures: Great Barrington is perfect for skiing and exploring picturesque state parks and nature reserves.
  • Historic charm: Discover the town's rich history through its historic houses and local attractions like Yard Great Barrington.
  • Charming neighborhoods: Stroll through delightful areas like Railroad Street and Beachwood Drive, each offering a unique vibe.
  • Family-friendly activities: The town offers a mix of fun for families, couples, and solo travellers alike.
  • Diverse accommodations: Choose from cozy cabins, charming cottages, and modern condos to suit any travel style.

Popular types of accommodation in Great Barrington

If you're planning a getaway to Great Barrington, the next step is selecting the perfect accommodation. From cozy houses and charming cottages to modern condos, you'll find a variety of options to suit your needs. Whether you're looking for spacious home rentals or intimate cabin rentals, Great Barrington offers many bedrooms and delightful choices for every type of traveler. Explore your options and make your stay truly memorable.

  • Houses: The top choice for visitors to Great Barrington, these homes offer spacious accommodations ideal for families or groups.
  • Condos: A popular selection for those seeking modern amenities, these units provide a comfortable and convenient stay.
  • Cottages: These charming retreats are perfect for a cozy getaway, surrounded by nature’s beauty.
  • Apartments: A practical option for solo travellers or couples, offering a home-like atmosphere in the heart of town.
  • Cabins: A delightful choice for those wanting a rustic experience, often nestled in serene woodland settings.**

Top attractions in and around Great Barrington

Great Barrington, Massachusetts, is an ideal destination for skiing and outdoor adventures. Visitors can explore historic houses, national and state parks, and nature reserves, offering rich cultural and adventure experiences. Don't miss the opportunity to discover local gems like Yard Great Barrington and other attractions that showcase the area's charm. Whether you're travelling solo, with family, or friends, Great Barrington has something for everyone to enjoy.

  • National Shrine of the Divine Mercy: A serene place of worship located 11.3km from Great Barrington, this shrine is a haven for spiritual reflection, featuring beautiful architecture and tranquil gardens that evoke a deep sense of peace and culture.
  • Housatonic River: Just 161m from Great Barrington, this picturesque river offers stunning scenery perfect for outdoor activities like kayaking and fishing, providing a refreshing escape into nature.
  • Lake Buel: Nestled within Great Barrington, Lake Buel boasts a lovely beach and romantic views, ideal for leisurely strolls, picnics, and soaking in the scenic beauty of the area.

Things to do recommended for couples

For a romantic getaway in Great Barrington, hit the slopes at Ski Butternut or Catamount Ski Area for thrilling skiing adventures. Afterward, unwind at Furnace Brook Winery at Hilltop Orchards, where you can enjoy delightful wine and a charming atmosphere, perfect for couples.

Things to do recommended for families

Your family will love exploring Lake Mansfield Park in Great Barrington, where you can relax and enjoy nature. A short drive away, Tyringham Cobble and Goose Pond Reservation offer similar wellness vibes, making them perfect spots for a peaceful day outdoors together.

Things to do recommended for groups

Groups visiting Great Barrington can enjoy a captivating performance at the Mahaiwe Performing Arts Center, embark on an exhilarating adventure at Catamount Aerial Adventure Park, and indulge in shopping at the Lee Premium Outlets for a delightful mix of entertainment and local charm.

*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 traveling with a group, family, pets, or seeking extended stays, it's important to prioritize your preferences. Here are some helpful Vrbo booking tips for you.

  • Traveling to Great Barrington with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor space for group gatherings. Thankfully, you can easily refine your search on Vrbo to include all these options and much more.
  • Traveling to Great Barrington with young kids: Traveling with young kids can be quite the adventure. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that are enjoyable for the whole family.
  • Taking your pets with you to Great Barrington: For many, a family getaway wouldn’t feel complete without their furry companion by their side. If this resonates with you, be sure to explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Great Barrington: If you're in search of vacation rentals offering 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 spot, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Great Barrington

Great Barrington, Massachusetts, is a hidden gem for those seeking a mountain getaway filled with adventure and relaxation. With its stunning scenery and friendly atmosphere, you'll find numerous activities, from skiing to exploring charming neighborhoods like Railroad Street and Beachwood Drive. This vibrant town offers a perfect blend of family-friendly fun and romantic spots, making it an ideal destination for any traveler looking to unwind and connect with nature.

  • Lenox: Situated 19.3km from Great Barrington, Lenox offers a delightful mix of entertainment, romance, and family-oriented activities. This charming city is renowned for its vibrant arts scene, with venues hosting music concerts and theatrical performances. Outdoor enthusiasts can indulge in skiing during the winter months at nearby slopes. Notable attractions include beautiful lakes and majestic mountains, making it a picturesque destination for nature lovers. Lenox is also home to event conference venues, perfect for those looking to blend leisure with professional engagements.
  • The Berkshires: Located 17.7km away, The Berkshires is a haven for outdoor adventurers and those seeking stunning scenery. This region is famed for its ski fields and resorts, attracting thrill-seekers throughout the winter. The natural surroundings boast breathtaking views of lakes and mountains, providing excellent hiking trails and opportunities for fishing and kayaking in the warmer months. Visitors can experience the perfect balance of adventure and relaxation, making it an ideal spot for families and nature enthusiasts alike.
  • Stockbridge: Just 11.3km from Great Barrington, Stockbridge is steeped in culture and offers a romantic setting for visitors. The city is known for its rich artistic heritage, featuring music concerts and theatre performances. Explore local landmarks such as monuments and shrines that reflect the area's history. Stockbridge's charming atmosphere, combined with its artistic offerings, makes it a perfect destination for couples and culture aficionados looking to immerse themselves in the local arts scene.

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

Booking with Vrbo is simple

Are you hoping to save on your next getaway? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that meets your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect spot for your next adventure.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly hub for planning your travels. You can easily create new trips, continue from where you last stopped, or review and organize your travel plans. Your saved or booked properties will be neatly arranged under the sections for Potential, Upcoming, or Current Trips. To get started with Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

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)
  • 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)
  • 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 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?
When considering a vacation rental in Great Barrington, Massachusetts, the downtown area is an excellent choice. This vibrant neighbourhood is not only conveniently located but also filled with charm and character. You'll find a delightful array of shops, restaurants, and cafés that cater to various tastes, making it easy to enjoy local cuisine and culture. The nearby Mahaiwe Performing Arts Centre is a popular attraction, offering a variety of performances, from live music to theatre productions, which can enhance your stay.

Another appealing neighbourhood is Housatonic, located just a short drive from downtown. This area has a quaint, small-town feel and is close to the scenic Housatonic River. It's superb for those who enjoy outdoor activities, as you can easily access walking trails and parks. The historic Housatonic Railroad Station adds a touch of history to your visit, while the serene environment makes it an ideal spot for relaxation.
How much does it cost to rent a vacation home in Great Barrington?
Prices for vacation rentals in Great Barrington vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Great Barrington to more spacious homes.
Are there any discounts for Great Barrington vacation house rentals?
You can find great discounts on house rentals in Great Barrington on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Great Barrington?
For renting a beach house in Great Barrington, Massachusetts, the area around Lake Mansfield is an excellent choice. This picturesque spot offers access to a lovely sandy beach, and many properties nearby come equipped with amenities such as outdoor decks, barbecues, and spacious living areas, superb for families or groups looking to enjoy the serene lakeside setting. Visitors can expect fully equipped kitchens to facilitate self-catering, and some rentals may even feature private docks for swimming or kayaking.
Where are the best Great Barrington ski resort rentals?
For those seeking rental properties near ski resorts in Great Barrington, Massachusetts, the area offers convenient access to Butternut Ski Area, located just a short drive away. In the town itself, travellers can find a variety of accommodations ranging from cosy cabins to modern condominiums, suiting different group sizes and preferences. Many properties come equipped with essential amenities such as kitchens or kitchenettes, allowing guests to prepare meals after a day on the slopes.

The neighbourhood surrounding Main Street provides a vibrant atmosphere with easy access to local shops, cafes, and restaurants, making it an ideal base for travellers. Additionally, many rentals in this area feature cosy living spaces with fireplaces, superb for unwinding after an active day outdoors. For those interested in more upscale options, there are also elegant homes that may include amenities like hot tubs or expansive decks with picturesque views of the surrounding mountains.
What is the most popular type of vacation rental accomodation in Great Barrington?
In Great Barrington, vacation houses are the most popular type of rental, with around 81 available throughout the area. These properties are often situated in picturesque neighbourhoods, providing a serene escape while being close to local attractions such as the historical downtown and the scenic Berkshire Mountains. Most vacation houses feature spacious living areas, fully equipped kitchens, and outdoor spaces like patios or decks for enjoying the natural surroundings.
Are there any family house rentals in Great Barrington?
In Great Barrington, Massachusetts, families will find a wealth of suitable vacation rentals—around 82 options available in the area. This charming town, located in the Berkshires, is an ideal destination for family getaways, with many properties located near the vibrant downtown, where visitors can enjoy local shops, dining, and cultural attractions.

Many of these homes offer spacious living areas, fully equipped kitchens superb for preparing family meals, and outdoor spaces for children to play. Amenities like Wi-Fi and laundry facilities are commonly included, enhancing the overall comfort of the stay.
Can I rent a vacation home with a pool or hot tub in Great Barrington?
In Great Barrington, there are several vacation homes available for rent that feature pools and hot tubs, with around 19 options to choose from. This picturesque town in the Berkshires is known for its charming downtown area and proximity to outdoor activities. You can find rentals in neighbourhoods such as the scenic Lake Buel area, where properties often offer serene views and easy access to water activities.
Can I find long-stay vacation rentals in Great Barrington?
A long-stay vacation rental in Great Barrington is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Great Barrington?
In Great Barrington, there are numerous pet-friendly house rentals available, with around 64 options for travellers seeking to bring their furry friends along. This charming town in the Berkshires offers a mix of modern and rustic accommodations, often featuring amenities such as spacious backyards, fully equipped kitchens, and cosy living areas, ideal for families or groups. Many properties are designed to make both pets and their owners comfortable, with features like pet-friendly outdoor spaces and nearby walking trails.
Are there any remote work vacation rentals in Great Barrington?
In Great Barrington, Massachusetts, there is a wealth of options for remote work vacation rentals, with around 102 properties available to choose from. This charming town, located in the Berkshire Mountains, is ideal for those looking to combine work and leisure. Many of these rentals are equipped with essential amenities for remote work, including reliable Wi-Fi, dedicated desk spaces, and comfortable office chairs.

Travellers can expect properties that feature laptop workspaces and even larger setups with computer monitors, providing a conducive environment for productivity. Additionally, some rentals offer secure safes, ensuring peace of mind for your belongings while you focus on work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Great Barrington vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Great Barrington with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Great Barrington?
In Great Barrington, popular vacation rental amenities include fully equipped kitchens, which are essential for those looking to prepare their own meals during their stay. Most rentals feature cookware, dishware, and utensils, along with essential appliances such as stovetops, refrigerators, and microwaves. This allows guests to enjoy the flexibility of cooking at home while being close to local attractions such as the picturesque downtown area, the scenic Berkshire hills, and the nearby hiking trails.
When is the best time to visit Great Barrington for a vacation rental?
July is the most popular month to visit Great Barrington, drawing in travellers eager to experience the town's vibrant summer charm. The peak season runs from June to August, offering a delightful blend of outdoor activities, cultural events, and local festivals. During these months, you can enjoy everything from hiking in the nearby Berkshire Mountains to exploring the picturesque downtown area, filled with unique shops and inviting eateries.

For those looking to enjoy comfortable weather, July typically sees temperatures in the mid to high 20s Celsius, superb for outdoor adventures and leisurely strolls around the scenic landscape. The lively atmosphere during this time makes it an ideal choice for families and friends seeking a memorable getaway.

If you're considering a more budget-friendly option, November is a wonderful time to visit Great Barrington. While it's outside the bustling summer season, the fall foliage creates a beautiful backdrop for exploration. This quieter month allows for peaceful hikes and a chance to appreciate the stunning autumn colours without the crowds.
How early should I book a Great Barrington vacation rental?
Book your Great Barrington vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Great Barrington home rental booking on Vrbo?
To find Great Barrington vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Great Barrington vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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