Destination guide

Beautiful border town wears its art on its sleeve

When you book a Brattleboro vacation rental, you'll find yourself in the midst of a charming New England town. Tucked away in eastern Vermont, at the confluence of the West and Connecticut Rivers, Brattleboro borders New Hampshire to the east and is just a 20-minute drive north of the Massachusetts state line. Budding artists call the picturesque village home, drawn by the siren sound of its numerous galleries, museums, and performance spaces. There's no shortage of outdoor recreational activities either, as nearby mountains offer ski resorts and area parks provide a variety of year-round activities.

Things to do

Bring the curtain down on a day filled with art and activity

The Vermont Jazz Center is a local favorite and stages concerts and workshops, so if you want to embrace your inner musician, it's the place to go. Kids will enjoy shows produced by the New England Youth Theatre, while adults will be entertained by the Vermont Theatre Company, which stages everything from classic to contemporary shows. Cultural excursions continue at the Brattleboro Museum and Art Center. If you're trying to be more active, Living Memorial Park features an Olympic-size pool, baseball fields, hiking trails, playgrounds, picnic facilities, and tennis, basketball, and volleyball courts. In the winter, the park also offers opportunities for ice skating and skiing.

Activities

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.

Weather

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.

Natural features

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.

How to get there

Transportation options to and around Brattleboro

Fly into Springfield, VT (VSF-Hartness State), the closest airport, located 33.9 mi (54.5 km) from the city center.

If you'd rather travel by train, you can make your way to Brattleboro Station.

Where to stay around Brattleboro?

Our 2019 property listings offer a large selection of 704 vacation rentals near Brattleboro. From 45 Cabins to 318 Houses, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Brattleboro for a holiday or a weekend are on HomeAway.

What is the best area to stay when traveling to Brattleboro?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Brattleboro:

  • Stratton Mountain Resort: 98 vacation rentals
  • West Dover: 642 vacation rentals
  • Bondville: 195 vacation rentals
  • Newfane: 65 vacation rentals
  • Bellows Falls: 31 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular points of interest near where I can stay when traveling to Brattleboro?

HomeAway offers a large selection of vacation rentals near lovely places in Brattleboro. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Brattleboro Common: 544 vacation rentals
  • Vermont Jazz Center: 409 vacation rentals
  • Brattleboro Country Club: 559 vacation rentals
  • Brattleboro Station: 520 vacation rentals
  • Creamery Covered Bridge: 561 vacation rentals

But there are many other points of interest around Brattleboro listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Cabins in Brattleboro?

Yes, of course. HomeAway has 45 Cabins in Brattleboro. Our other popular types of vacation rentals in Brattleboro include:

  • Houses: 318 rentals available
  • Cottages: 45 rentals available
  • Farmhouses: 17 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Condos/Apartments and more.

Can I find a vacation rental with pool in Brattleboro?

Yes, you can select your preferred vacation rental with pool among our 211 vacation rentals with pool available in Brattleboro. Please use our search bar to access the selection of vacation rentals available.