Brattleboro vacation rentals

We found 1,305 vacation rentals — enter your dates for availability

Discover a selection of 24 homes, 10 apartments, and other vacation rentals in Brattleboro that are perfect for your trip. Whether you’re staying in a vacation home with your kids and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, which might include a pool and a washer and dryer. Whatever you're looking for, you'll find a rental that has what everyone needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Brattleboro

Showing deals for:Jul 3 - Jul 10

Image gallery for End of season discount: Vermont winter chalet near Mount Snow and Wilmington

Living area with wood stove
10 out of 10, Exceptional, (26 reviews)
Exceptional
(26 reviews)

End of season discount: Vermont winter chalet near Mount Snow and Wilmington

West Dover

8% off
Price is $396
$2,773 for 7 nights
All fees included
End of season discount: Vermont winter chalet near Mount Snow and Wilmington

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Find out more about Brattleboro

Why visit Brattleboro

  • Outdoor Adventures: Enjoy skiing, hiking, and exploring beautiful nature reserves and serene lakes.
  • Family-Friendly Activities: Brattleboro offers a variety of excursions suitable for families, ensuring fun for all ages.
  • Charming Neighborhoods: Stroll through quaint neighborhoods and experience the warm, friendly atmosphere of the town.
  • Diverse Accommodations: Choose from cozy cabins, charming vacation homes, and convenient motels to suit your stay.
  • Cultural Experiences: Engage with local art, music, and cultural events that reflect the town's vibrant spirit.

Popular types of accommodation in Brattleboro

If you're exploring Brattleboro for your next getaway, you'll find a variety of popular vacation rentals to suit your needs. Choose from charming houses, cozy condos, and rustic cabins. Whether you're searching for an apartment in Brattleboro, a spacious bedroom apartment, or a convenient motel, we have options for every traveler. Discover the perfect home for your stay and enjoy all that this vibrant town has to offer.

  • Houses: The top choice for travelers, these homes offer spacious accommodations perfect for families or groups seeking comfort and privacy.
  • Condos: A popular option, condos provide modern amenities and are often located near attractions, making them ideal for convenience.
  • Cabins: Perfect for those looking for a serene escape, cabins offer a cozy retreat surrounded by nature.
  • Apartments: These stylish rentals are great for couples or solo travelers wanting a home-like experience in the heart of the city.
  • Cottages: Quaint and charming, cottages provide a delightful atmosphere for a relaxing getaway.**

Top attractions in and around Brattleboro

Brattleboro, Vermont, is an ideal destination for ski and adventure enthusiasts, offering a variety of outdoor activities. Visitors can explore beautiful nature reserves, serene lakes, and lush forests, making it perfect for those seeking adventure and cultural experiences. Whether you're traveling solo, as a couple, or with family, Brattleboro's attractions cater to all types of travelers looking to enjoy the great outdoors.

  • Brattleboro Common: This urban park is a vibrant hub in the heart of Brattleboro, perfect for family outings and outdoor activities. Enjoy its spacious lawns, seasonal events, and scenic views while soaking in the city atmosphere.
  • Hogback Mountain Conservation Area: A serene natural reserve offering breathtaking vistas and a variety of trails for hiking enthusiasts. Explore its rich biodiversity and peaceful surroundings, ideal for nature lovers.
  • Madame Sherri Forest: Located 2 miles from Brattleboro, this enchanting forest invites adventure seekers to explore its scenic trails, unique rock formations, and lush greenery, making it a perfect spot for outdoor escapades.

Things to do recommended for couples

For a romantic getaway in Brattleboro, enjoy a live performance at The Stone Church, indulge in luxury at the Brattleboro Country Club, or savor exquisite wines at Honora Winery, where the atmosphere is perfect for couples seeking romance and entertainment.

Things to do recommended for families

Families visiting Brattleboro can have a blast at Brattleboro Bowl, an exciting arcade and adventure zone perfect for kids. Enjoy a day filled with fun games and family-friendly activities in a lively atmosphere that everyone will love.

Things to do recommended for groups

Explore the Brattleboro Farmers' Market for fresh local produce and crafts, shop at Vermont Marketplace for entertainment and family fun, and catch a show at the historic Latchis Theatre for a taste of culture and romance. Perfect activities for a memorable group vacation.

*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 Brattleboro

If you're traveling with a group, family, pets, or planning an extended stay, be sure to prioritize your preferences during your search. Here are some helpful Vrbo booking tips for you.

  • Traveling to Brattleboro with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Brattleboro with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Brattleboro: For many families, a vacation isn't truly enjoyable without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Brattleboro: If you're seeking vacation rentals with great offers 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 features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Brattleboro

Brattleboro, Vermont, offers a delightful blend of adventure and relaxation, making it an ideal family getaway. Explore the charming neighborhoods and experience the warm, friendly atmosphere while enjoying skiing and outdoor sports. With its secluded spots and family-friendly excursions, Brattleboro is perfect for those seeking both excitement and tranquility. The surrounding regions also provide excellent opportunities to make the most of the warmer months, ensuring a memorable vacation for everyone.

  • Keene: Located 15 miles from Brattleboro, Keene is a vibrant city known for its stunning outdoor scenery and adventurous spirit. The area is a haven for outdoor enthusiasts, offering ample opportunities for skiing at nearby ski resorts and exploring the picturesque landscape filled with lakes and mountains. Visitors can enjoy the lively atmosphere of downtown Keene, which features charming shops, local eateries, and cultural attractions, including the modern Keene State College. Whether you’re hitting the slopes or enjoying a leisurely walk by the lake, Keene promises an unforgettable travel experience.
  • Wilmington: Situated 16 miles from Brattleboro, Wilmington is an outdoor lover's paradise, particularly famous for its skiing and sports activities. The town is surrounded by beautiful mountains, making it a prime destination for winter sports enthusiasts looking for ski fields and resorts. Wilmington also boasts stunning valley views and serene lakes, perfect for summer activities like hiking, fishing, and boating. With its small-town charm, visitors can find cozy accommodations and delightful dining options, making it an excellent stop for adventure seekers and nature lovers alike.
  • West Chesterfield: Just 4 miles from Brattleboro, West Chesterfield offers a delightful blend of outdoor adventure and scenic beauty. Known for its close-knit community and tranquil atmosphere, this city is an ideal spot for outdoor activities such as skiing, with access to excellent ski resorts and fields. The surrounding landscape features breathtaking mountains, lakes, and valleys, providing a picturesque backdrop for hiking, biking, and exploring. With its proximity to Brattleboro, West Chesterfield is an easy getaway for those looking to experience the beauty of Vermont’s outdoors.

Best time to go to Brattleboro

If you're planning a trip to Brattleboro, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from July to September, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January22.5°F (-5.3°C)Light RainMostly SunnySlightly LowModerately High
February24.4°F (-4.2°C)Light RainMostly CloudyAverageModerately High
March32.2°F (0.1°C)Light RainMostly SunnyAverageAverage
April44.4°F (6.9°C)Light RainMostly SunnyAverageModerately Low
May56.8°F (13.8°C)Light RainMostly SunnyAverageModerately Low
June64.6°F (18.1°C)Light RainMostly SunnyAverageAverage
July70.7°F (21.5°C)Light RainMostly SunnySlightly HighAverage
August68.7°F (20.4°C)Light RainMostly SunnySlightly HighAverage
September61.5°F (16.4°C)Light RainMostly SunnySlightly HighModerately Low
October50.0°F (10.0°C)Light RainMostly SunnyAverageAverage
November37.8°F (3.2°C)Light RainMostly SunnySlightly LowAverage
December29.1°F (-1.6°C)Light RainMostly SunnySlightly LowModerately High

Booking with Vrbo is a breeze

Looking to save on your next vacation? Consider being flexible with your travel dates, as this can lead to significant price differences. Also, extending your stay can often result in valuable savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to narrow down your search by price, location, and type of vacation rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient way to plan new trips, manage your ongoing arrangements, or organize your bookings. Your saved and booked properties are categorized into Potential, Upcoming, and Current Trips for easy access. To start exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The riverside setting of Brattleboro is ready to explore

Come and experience Brattleboro and its monuments, entertainment and art galleries. Renowned for its skiing, shopping and theaters, this city welcomes all visitors. Whether you're planning a family vacation, friends trip or romantic retreat, HomeAway has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Sightseeing in and around Brattleboro

Are you hoping to find attractions to see while you're in town? Venture out of your cozy vacation rental and experience everything that Brattleboro has to offer. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Mount Snow (19.8 mi / 31.9 km)
  • Stratton Mountain Resort (24.7 mi / 39.7 km)
  • Mount Snow Golf Course (16.7 mi / 26.9 km)
  • The Hermitage Golf Club (17 mi / 27.4 km)
  • Berkshire East Ski Resort (22.8 mi / 36.7 km)
  • Jamaica State Park (23.9 mi / 38.5 km)

Forts, festivals, and fun times in Brattleboro

Culture vultures will love downtown Brattleboro's monthly Gallery Walk, when local artists showcase their latest work. No matter what time of year you book a Brattleboro vacation rental, you're sure to coincide with a special event, such as the Winter Carnival, the Brattleboro Women's Film Festival, or the Brattleboro Free Folk Festival. Sports junkies should visit the Harris Hill Ski Jump, home to major competitions every year. Get your own workout in at Fort Dummer State Park, a 218-acre space with hiking trails, or at Stratton Mountain's ski resort, just 45 minutes away.

Brrrrr! Blustering blizzards in Brattleboro

When it's time for winter, Brattleboro can get up to 92 inches of snow each year. Yes, you read that right. Daytime highs in the winter typically hover near freezing, with lows dipping into the teens. On the flip side, summers are hot and humid, with temperatures in the mid-80s, but heavy showers and thunderstorms are pretty common. Springs are mild with highs in the 60s and 70s, but you'll be dodging raindrops in May, typically the wettest month. Fall is a popular time for booking Brattleboro vacation rentals, as the region sees colorful foliage and comfortable daytime highs in the 50s and 60s.

Down on the farm and up in the mountains, nature runs wild

The town's 2 main waterways, the West River and the Connecticut River, flow past lush, fertile farmland. Some working farms in the area are open for tours, giving you the chance to see dairy cows at work and petting zoos filled with sheep, goats, chickens, and pigs. The surrounding countryside is also dotted with maple trees, which are tapped into to make Vermont's famed syrup. You could also check out the Green Mountains, a rugged region with waterfalls, cliffs, ponds, and lakes. While hiking through the mountains, keep an eye out for wildlife such as black bears, mountain lions, and elk, while falcons circle overhead.

Traveling to and around Brattleboro

Fly into Springfield, VT (VSF-Hartness State), the closest airport, located 34 mi (54.7 km) from the city center.

If you're traveling by train, the main station serving the city is Brattleboro Station.

Frequently asked questions

How much does it cost to rent a vacation home in Brattleboro?
Prices for vacation rentals in Brattleboro 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 Brattleboro 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 Brattleboro vacation house rentals?
You can find great discounts on house rentals in Brattleboro 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 Brattleboro ski resort rentals?
For the best ski resort rentals near Brattleboro, Vermont, travelers should look to the nearby Mount Snow area, which is approximately 30 minutes away. In the town of West Dover, which serves as a gateway to Mount Snow, there are a variety of vacation homes and condos available. Many of these properties feature amenities such as open living spaces with fireplaces, fully equipped kitchens, and private balconies or decks that offer stunning views of the mountains. Some rentals also come with community amenities, like heated pools and hot tubs, superb for relaxing after a day on the slopes.

In addition to West Dover, the nearby town of Wilmington also offers charming cottages and lodge-style accommodations that cater to skiers. These properties often include cozy furnishings, multiple bedrooms for families or groups, and convenient access to local dining and shops. The proximity to snowshoeing and cross-country skiing trails enhances the appeal for travelers looking for a winter getaway.

For those interested in exploring beyond skiing, Brattleboro itself offers a vibrant arts scene, local breweries, and scenic river views, making it an excellent base for both winter sports and cultural experiences.
What is the most popular type of vacation rental accomodation in Brattleboro?
In Brattleboro, vacation houses are the most popular type of rental, with about 17 available throughout the area. These houses provide spacious rooms ideal for families or groups, often featuring multiple bedrooms, fully equipped kitchens, and outdoor areas for relaxation. Additionally, there are around 10 apartments that offer a more compact living space, typically including kitchen facilities and cozy living areas, great for couples or solo travelers. For those seeking a more rustic experience, several cabins, chalets, and cottages can be found, providing a charming and serene backdrop to enjoy the natural beauty of Vermont.
Are there any family house rentals in Brattleboro?
In Brattleboro, Vermont, there are 14 family-friendly house rentals available, making it a great choice for families seeking a cozy getaway. The area is known for its picturesque landscapes and vibrant arts scene, providing plenty of activities for all ages. Many of these homes feature spacious living rooms, fully equipped kitchens for preparing family meals, and outdoor areas where children can play.

Families can also enjoy amenities such as game rooms or cozy fireplaces, enhancing the at-home feel. Located near attractions like the Brattleboro Museum & Art Center and the scenic Connecticut River, visitors will have no shortage of exploration opportunities.
Can I rent a vacation home with a pool or hot tub in Brattleboro?
In Brattleboro, there are several vacation homes available for rent that feature pools and hot tubs. This charming town in Vermont offers a picturesque setting with access to both outdoor activities and local culture. Travelers can expect amenities such as private pools, hot tubs, and spacious outdoor areas for relaxation and entertainment. Many properties also include fully equipped kitchens, comfortable living spaces, and sometimes even scenic views of the surrounding landscapes.
Can I find long-stay vacation rentals in Brattleboro?
A long-stay vacation rental in Brattleboro is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Brattleboro?
In Brattleboro, there are several pet-friendly house rentals available, making it a great destination for travelers looking to bring their furry friends along. The area offers a variety of vacation homes that typically feature amenities such as full kitchens, spacious living areas, and outdoor spaces where pets can roam. Many properties are located near scenic spots, providing a peaceful retreat with the convenience of local shops and dining options nearby.

Brattleboro is also close to several parks and outdoor areas, such as the Retreat Farm and the West River Trail, which are great for walking and enjoying nature with pets. The charming downtown area has pet-friendly cafes and shops, enhancing the overall experience for visitors traveling with animals.
Are there any remote work vacation rentals in Brattleboro?
In Brattleboro, Vermont, there are several remote work vacation rentals available, with around 27 options for travelers seeking a conducive environment for working remotely. Many of these properties come equipped with complimentary Wi-Fi, both in rooms and common areas, ensuring that you can stay connected during your stay. Additionally, many rentals permit events, making them suitable for small gatherings or meetings.

The town itself is rich in artistic culture and offers a variety of local cafes and co-working spaces for those looking to change their work environment. With its charming downtown, Brattleboro is not only a great place to work but also an inviting destination for exploring local shops, restaurants, and the scenic beauty of the surrounding Vermont landscape. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Brattleboro vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Brattleboro with parking available—perfect for families or travelers 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 Brattleboro?
In Brattleboro, popular vacation rental amenities include kitchens, allowing guests to prepare their own meals and enjoy a home-like experience. Many properties also offer onsite parking, making it convenient for travelers with vehicles. Decks or patios are common features, providing outdoor space to relax and take in the scenic views of Vermont. Additionally, some rentals are pet-friendly, accommodating those traveling with furry companions. Travelers can also expect coffee and tea makers in most rentals, great for enjoying a warm beverage in the comfort of their accommodations.
When is the best time to visit Brattleboro for a vacation rental?
The best time to visit Brattleboro for a vacation rental is during the peak season from July to September. This period is particularly popular among travelers looking to enjoy the vibrant summer atmosphere, with numerous outdoor festivals, art fairs, and live music events that showcase the town's rich cultural heritage. The warm temperatures, usually ranging from the mid-60s to mid-80s Fahrenheit, offer a great backdrop for exploring the scenic Connecticut River, hiking nearby trails, and enjoying the local cuisine.

July stands out as the most sought-after month, drawing visitors eager to experience Brattleboro's lively community spirit. You'll find plenty of opportunities for outdoor activities, such as kayaking, cycling, or simply strolling through the charming downtown area, where local shops and eateries thrive.

For those who appreciate a quieter experience, consider visiting in November. This month provides a serene atmosphere, with the beauty of late fall foliage still lingering. It's a great time for cozy indoor activities, like visiting local art galleries and enjoying a warm beverage at a café.

Ultimately, your ideal time to visit Brattleboro will depend on whether you're drawn to the bustling energy of summer or the peaceful charm of the fall season.
How early should I book a Brattleboro vacation rental?
Book your Brattleboro 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.
What are the top attractions in Brattleboro, Vermont, United States of America?
In Brattleboro, visitors can explore a charming blend of natural beauty and cultural attractions. The downtown area features unique shops, art galleries, and a vibrant dining scene that reflects the town's artistic spirit. One of the highlights is the Brattleboro Museum & Art Center, which showcases contemporary art and local history exhibits.

For nature enthusiasts, the nearby Connecticut River offers opportunities for kayaking and scenic walks along the riverbank. The Retreat Farm, located just a short distance from the town center, provides a lovely space for family outings, featuring walking trails, farm animals, and seasonal events.

Additionally, the Whetstone Brook runs through the area, providing picturesque views and peaceful spots for relaxation.
Can I change or cancel my Brattleboro home rental booking on Vrbo?
To find Brattleboro 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 Brattleboro 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 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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