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Brattleboro vacation rentals

We found 1,151 vacation rentals — enter your dates for availability

your current months are May, 2024 and June, 2024.
May 2024
June 2024
Discover a selection of 16 homes 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.

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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

What is the best area to stay in Brattleboro when booking a vacation rental?

Among the more desired neighborhoods to book a vacation property in Brattleboro is West Brattleboro. Find your dream stay with Vrbo and experience this area like a local.

What is the most popular type of vacation rental accommodation in Brattleboro?

Houses are the most popular kind of vacation rental in Brattleboro, according to our data. Even if you've got something else in mind, Vrbo has properties in all shapes and sizes. Filter our options to find your perfect match.

How much does it cost to rent a vacation rental in Brattleboro?

The average price for a vacation rental in Brattleboro can vary based on factors like property type, season and length of stay. Whether you're dreaming about a sprawling house with room for friends and family or a quaint cottage for just you and your sweetheart, just enter your travel dates to discover stays with unbeatable value.

How much does it cost to rent a beach house in Brattleboro?

When you travel and the style and size of the property will help determine the cost of your beachside stay. Type in your Brattleboro travel dates to see all your options on Vrbo. Did someone just say "private pool"? Use our filters to pick the amenities and features you want in your vacation home.

Are there pet-friendly vacation rentals in Brattleboro?

There are, yes. You'll have your pick of 11 vacation rentals that allow pets in Brattleboro on Vrbo. Our furry best friends deserve a getaway too, so simply use our search function for pet-friendly vacation rentals to find a pad where your pup can lap up the good times.

Can I rent a house with a pool in Brattleboro?

Add an extra element of fun to your trip by staying in one of the two houses with a private pool in Brattleboro. Use our search filter to find properties with pools on Vrbo, then spend leisurely days splashing about in a swimming pool that's all yours.

What are popular rental amenities in Brattleboro?

When it comes to rental amenities that guests prefer in Brattleboro, nearby museums, a nearby river and a barbecue grill are at the top of the list. With Vrbo vacation rentals, you'll have options to fit your style and taste, whether you're vacationing with family members, friends or even pets.

Are there large group vacation rentals in Brattleboro?

Choose from three vacation properties in Brattleboro that can host a group of 10 or more guests. Whether you're planning a family vacation or some kind of special event, there's plenty of space to get your favorite people together under the same roof.

Are there vacation rentals in Brattleboro that welcome kids?

With 11 family-friendly vacation rentals to select from in Brattleboro, now is a fantastic time to introduce your kids to the pleasures of travel. Check our "Properties good for families" filter box to search for stays that come with amenities ideal for families on the move, like multiple bedrooms, backyards, hot tubs and entertainment areas.

What are the top attractions for families in Brattleboro?

There are loads of amazing things to see and do with the family in Brattleboro, such as:

  • Brattleboro Bowl
  • Southern Vermont Natural History Museum
  • Wantastiquet Mountain

Are there one-bedroom vacation rentals in Brattleboro?

You can choose from two one-bedroom rentals in Brattleboro. Whether you'd prefer a cozy chalet or an upmarket condo, Vrbo's one-bedroom properties are ideal if you don't require huge amounts of space. One of the major perks of having your own place? You'll never need to share your getaway with strangers.

Can I find two-bedroom vacation rentals in Brattleboro?

Take off with your loved ones and experience complete comfort and privacy in one of the two two-bedroom vacation homes Brattleboro has to offer.

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