Great Barrington holiday lettings

We found 694 holiday rentals — enter your dates for availability

Discover a selection of 106 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:2 Oct - 9 Oct

Image gallery for The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History

Interior
10 out of 10, Exceptional, (254 reviews)
Exceptional
(254 reviews)

The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History

Lenox

8% off
Price is £6,122
for 7 nights, 1 home
£875 per night
includes taxes & fees
The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History

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Why visit Great Barrington

  • Outdoor Adventures: Enjoy skiing and hiking in the beautiful surrounding nature reserves, offering breathtaking views and diverse trails.
  • Cultural Experiences: Immerse yourself in the local arts scene at the Great Barrington Public Theatre and Arts Market.
  • Charming Downtown: Stroll through picturesque streets filled with unique shops, delightful eateries, and a friendly atmosphere.
  • Seasonal Events: Participate in various holiday events and activities throughout the year, showcasing the town's spirited community.
  • Scenic Accommodation: Relax in cosy vacation rentals that provide a warm and inviting experience amidst stunning landscapes.

Popular types of accommodation in Great Barrington

Your adventure in Great Barrington, Massachusetts, awaits. This charming town offers a delightful selection of vacation rentals, including private homes, condos, and cosy cottages. Enjoy complimentary hot breakfasts and a range of amenities such as fitness centres and business facilities. Explore the local attractions, including scenic trails and cultural landmarks, while experiencing the warm hospitality that Great Barrington is known for. Make your stay memorable in this enchanting New England destination.

  • Houses: These spacious and fully equipped homes offer a comfortable, home-like atmosphere, making them the top choice for visitors in Great Barrington.
  • Condos: Ideal for those seeking modern amenities and convenience, condos provide a stylish and compact living space.
  • Cottages: Quaint and charming, cottages offer a rustic escape amidst the natural beauty of the area.
  • Apartments: Perfect for shorter stays, apartments provide a practical and cosy living environment.
  • Cabins: Embrace the outdoors in a cabin, ideal for a serene retreat surrounded by nature.**

Top attractions in and around Great Barrington

Great Barrington, Massachusetts, is a charming destination perfect for skiing and outdoor adventures. Visitors can explore stunning nature reserves and historical sites, alongside enjoying the vibrant local culture at the Great Barrington Public Theatre and Arts Market. The town hosts various holiday events and activities throughout the year, making it an ideal spot for those seeking a mix of adventure and cultural experiences in a picturesque setting.

  • Lake Buel: A serene lake nestled in Great Barrington, Lake Buel offers picturesque scenery and a charming beach, perfect for outdoor activities and romantic escapes.
  • National Shrine of the Divine Mercy: A spiritual haven, this shrine invites visitors to explore its tranquil grounds and embrace its rich cultural significance, fostering reflection and peace.
  • Norman Rockwell Museum: Celebrating the iconic American artist, this museum showcases Rockwell's beloved works, providing insight into his artistry and cultural impact.

Things to do recommended for couples

Great Barrington offers a charming escape for couples. Stroll hand in hand through picturesque Main Street, enjoy a wine tasting at a local vineyard, or take a scenic hike in the nearby Berkshires. Don't forget to relax at a cosy café, soaking in the tranquil atmosphere together.

Things to do recommended for families

Families visiting Great Barrington can explore the scenic beauty of Lake Mansfield Park, enjoy a day of fun at the Berkshire Botanical Garden, and take part in seasonal activities like apple picking at local orchards, ensuring delightful family-friendly experiences throughout your stay.

Things to do recommended for groups

Groups visiting Great Barrington can experience the thrill of motor racing at Lime Rock Park, just 29km away, and embark on an adventurous zipline course at Catamount Aerial Adventure Park, only 10km from town, offering plenty of outdoor excitement.

*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 planning your trip, whether you're travelling with a group, with family, bringing your pets, or seeking extended stays, it's important to apply the appropriate filters to align with 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 space for group gatherings. Thankfully, you can easily apply filters 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 facilities like a private swimming pool. Additionally, it's wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Great Barrington: For many, a family holiday wouldn't feel complete without their furry companion by their side. If you can relate, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Great Barrington: If you’re in search of holiday rentals offering discounts for stays of a month or more, you’ve come to the perfect destination. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don’t forget to include options such as 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, is a charming city that beckons visitors with its stunning scenery and vibrant downtown. Explore the local shops and eateries, or partake in seasonal holiday events that capture the town's friendly spirit. With opportunities for skiing and outdoor adventures, Great Barrington offers a delightful mix of relaxation and excitement, perfect for families and couples alike. Discover the warm atmosphere and picturesque landscapes that make this destination truly special.

  • Lenox: Located 19km from Great Barrington, Lenox is a charming town that offers a delightful blend of romance and culture. Known for its vibrant arts scene, visitors can enjoy a variety of entertainment options, including live music concerts and theatrical performances. For those who appreciate nature, Lenox is surrounded by stunning lakes and mountains, providing a picturesque backdrop for outdoor activities. The town is also home to venues for conferences and events, making it a popular spot for gatherings. Whether you're looking to explore the local arts or simply enjoy a peaceful retreat, Lenox has something for everyone.
  • The Berkshires: Situated 18km away from Great Barrington, The Berkshires is a haven for outdoor enthusiasts and adventure seekers. This region is renowned for its breathtaking scenery, which includes majestic mountains and tranquil lakes. Visitors can partake in a variety of outdoor activities, such as skiing at local resorts and enjoying the stunning ski fields. The Berkshires also hosts numerous events and conferences throughout the year, making it a vibrant community for both residents and tourists. The combination of natural beauty and adventure makes The Berkshires a must-visit destination.
  • Stockbridge: Just 11km from Great Barrington, Stockbridge is a quaint town steeped in romance and culture. It offers a unique blend of entertainment options, from music concerts to theatrical performances, ensuring a lively atmosphere. The town is notable for its beautiful lakes, historic monuments, and charming places of worship, which add to its cultural richness. Exploring Stockbridge provides an insight into the region's history and artistic heritage, making it an enriching experience for visitors looking for both relaxation and inspiration.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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

Booking with Vrbo is a breeze

Are you hoping to save some money on your upcoming journey? It might be beneficial to stay flexible with your travel dates, as prices can vary. Additionally, opting for a longer stay often leads to significant savings. To discover the ideal Vrbo property that fits your budget, feel free to utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers a seamless way to plan your journeys, allowing you to start new trips, continue from where you last paused, or review and arrange your travel plans. You can easily find your saved or booked properties sorted into categories such as Potential, Upcoming, or Current Trips. To begin exploring 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)
  • 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)
  • 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?
When considering a holiday rental in Great Barrington, Massachusetts, the downtown area is often regarded as one of the best places to stay. This charming neighbourhood offers a delightful mix of boutique shops, art galleries, and a variety of dining options, making it an ideal base for exploring the local culture. A popular attraction in the area is the Mahaiwe Performing Arts Centre, which hosts a range of live performances and events, adding to the vibrant setting of downtown.

Another appealing neighbourhood is the surrounding countryside, which provides a more tranquil experience. Here, visitors can enjoy the natural beauty of the Berkshires, with opportunities for hiking and outdoor activities just a short drive away. Additionally, the Norman Rockwell Museum is nearby, celebrating the works of the famed illustrator and providing insight into American art and culture.

In terms of properties, the downtown area features a range of options, from quaint inns to modern holiday rentals, suiting various preferences and budgets. The countryside offers charming cottages and homes, great for those seeking a peaceful retreat while still being close to the attractions of Great Barrington.
How much does it cost to rent a holiday home in Great Barrington?
Prices for holiday 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 traveling 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. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Great Barrington holiday 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 Great Barrington ski resort rentals?
For the best ski resort rentals in Great Barrington, visitors should focus on the areas around Butternut Ski Area, which is just a short drive from the town centre. The nearby neighbourhoods of Great Barrington itself and the quaint village of Housatonic offer a range of holiday rentals, including cosy cabins and spacious chalets, ideal for families or groups looking to enjoy a winter getaway.

Many properties in these locations come equipped with amenities such as full kitchens, fireplaces, and comfortable living spaces to unwind after a day on the slopes. Some rentals may also feature outdoor decks or hot tubs, great for soaking in after an exhilarating day of skiing.

In addition to skiing, Great Barrington boasts a vibrant arts scene, with local galleries and theatres contributing to its charm. The town is home to a variety of restaurants and shops, making it convenient for travellers to explore the local culture and cuisine. Properties in the heart of Great Barrington often allow easy access to these attractions, enhancing the overall experience.
What is the most popular type of holiday rental accomodation in Great Barrington?
In Great Barrington, holiday houses are the most prevalent type of holiday rental, with around 336 available throughout the area. These properties typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxing. Many of them are situated near the scenic attractions of the Berkshires, providing easy access to hiking trails and local parks. Additionally, there are about 48 cottages that offer a charming, rustic experience, complete with cosy interiors and often a fireplace. For those seeking a more compact option, around 20 apartments are available, ideal for couples or solo travellers, featuring essential amenities and convenient locations close to shops and restaurants. There are also several condos that provide a blend of comfort and modern living, often within well-maintained complexes.
Are there any family house rentals in Great Barrington?
In Great Barrington, there are a variety of family-friendly house rentals available, with around 82 options throughout the area. This charming town in the Berkshires offers a beautiful backdrop for family holidays, with properties situated in neighbourhoods that provide both comfort and convenience. Many homes feature spacious living rooms, fully equipped kitchens, and outdoor spaces where families can gather and enjoy the fresh air.

Visitors will find amenities such as Wi-Fi, laundry facilities, and sometimes even game rooms or private gardens. Proximity to attractions like the picturesque Lake Mansfield, which is great for swimming and picnicking, as well as the vibrant downtown area filled with shops and restaurants, ensures that there are plenty of activities for everyone.
Can I rent a holiday home with a pool or hot tub in Great Barrington?
In Great Barrington, there are plenty of holiday homes available for rent that feature pools and hot tubs, with around 21 options to choose from. This charming town in the Berkshires is known for its stunning natural scenery and vibrant cultural scene. Many of the properties come equipped with private pools and hot tubs, providing a ideal setting for relaxation after a day of exploring.

Travellers can expect amenities such as spacious outdoor areas, fully equipped kitchens, and comfortable living spaces, ideal for families or groups. Some rentals may also include features like fire pits, barbecue grills, and easy access to hiking trails, allowing guests to fully immerse themselves in the outdoors.
Can I find long-stay holiday rentals in Great Barrington?
A long-stay holiday 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, making it an excellent choice for travellers with furry companions. The area offers a charming mix of holiday homes that typically feature modern amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces for pets to enjoy. Many rentals also provide additional comforts like fireplaces, Wi-Fi, and laundry facilities, ensuring a pleasant stay.

The neighbourhood is surrounded by natural beauty, with easy access to various parks and outdoor activities. Nearby, visitors can explore the scenic paths of the Housatonic River Walk or venture into the vast landscapes of the Berkshire Mountains, where hiking trails are abundant and pet-friendly. Additionally, the town is home to pet-friendly cafes and shops, ideal for those travelling with pets.
Are there any remote work holiday rentals in Great Barrington?
In Great Barrington, Massachusetts, there are numerous remote work holiday rentals available, with around 424 options to choose from. This charming town in the Berkshires offers a blend of natural beauty and a vibrant cultural scene, making it an ideal setting for those looking to work remotely. Many of the properties feature essential amenities such as free Wi-Fi, dedicated workspaces, and comfortable living areas, allowing for a productive work environment.

Travellers can expect a variety of accommodations, including spacious homes and cosy cabins, often equipped with conveniences like full kitchens and outdoor spaces, superb for taking breaks amidst the stunning surroundings. The town's proximity to outdoor activities, including hiking and skiing in the nearby mountains, adds to its appeal for remote workers seeking a balance between work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Great Barrington holiday rentals with parking?
Vrbo offers a wide selection of holiday 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 rental amenities include kitchens, which allow guests to prepare their own meals, and outdoor spaces such as decks or patios, great for enjoying the scenic views of the Berkshires. Many properties also feature fireplaces, adding a cosy touch, especially during the colder months. Onsite parking is commonly available, making it convenient for those travelling by car. Additionally, travellers can expect coffee and tea makers in their rentals, ensuring a warm beverage is always at hand to start the day.
When is the best time to visit Great Barrington for a holiday rental?
The best time to visit Great Barrington for a holiday rental is during the peak season from June to August, with July being particularly popular among tourists. This vibrant period offers an array of outdoor activities, including hiking in the beautiful Berkshire Mountains and exploring local art galleries and shops. The warm summer weather, with temperatures typically ranging from 15 to 30 degrees Celsius, allows for comfortable sightseeing and enjoying the stunning natural surroundings.

During these summer months, you'll find a lively option filled with festivals and events, making it an ideal time for travellers. The picturesque town comes alive with outdoor concerts, farmers' markets, and opportunities to enjoy the local cuisine.

For those looking for a more budget-friendly experience, consider visiting in November. This quieter month showcases the charm of Great Barrington as the autumn colours linger, providing a beautiful backdrop for leisurely walks and exploration of the area's quaint streets and local attractions without the crowds.

Ultimately, your choice of when to visit Great Barrington will depend on whether you prefer the energetic vibe of the summer months or a more tranquil experience in the fall.
How early should I book a Great Barrington holiday rental?
Book your Great Barrington holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Great Barrington?
In Great Barrington, visitors can enjoy a charming mix of outdoor activities and cultural experiences. The downtown area is vibrant, featuring unique shops, galleries, and eateries that reflect the local community's artistic flair. A highlight is the Mahaiwe Performing Arts Centre, which hosts a variety of live performances and film screenings.

For nature enthusiasts, the nearby Monument Mountain offers hiking trails with stunning views of the Berkshires, making it a popular spot for both locals and visitors. The Appalachian Trail also runs through the region, providing ample opportunities for hiking and exploring the natural beauty of the area.

Additionally, the picturesque Lake Mansfield is superb for swimming, picnicking, and enjoying the serene surroundings.
Can I change or cancel my Great Barrington home rental booking on Vrbo?
To find Great Barrington holiday 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 holiday 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 as applicable.

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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