Photo by Shirley Rhodes

Brattleboro holiday lettings

We found 1,158 holiday rentals — enter your dates for availability

your current months are April, 2024 and May, 2024.
April 2024
May 2024
Discover a selection of 16 homes and other holiday rentals in Brattleboro that are perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll find the amenities that you need and want, which might include Wi-Fi and a pool. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

The riverfront setting of Brattleboro is ready to explore

Come and experience Brattleboro and its monuments, entertainment and art galleries. Renowned for its skiing, shopping and theatres, this city welcomes all visitors. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday 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 looking for attractions to visit in the area? Venture out of your cosy holiday rental and experience everything that makes Brattleboro a fun spot to go on holiday. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Mount Snow Golf Course (16.7 mi / 26.9 km)
  • The Hermitage Golf Club (17 mi / 27.4 km)
  • The Hermitage Club (18.2 mi / 29.4 km)
  • Mount Snow (19.8 mi / 31.9 km)
  • Berkshire East Ski Resort (22.8 mi / 36.7 km)
  • Jamaica State Park (24 mi / 38.6 km)

Exploring the natural features in Brattleboro

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Brattleboro is a great place to get outside. Here are some of the area’s most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Brattleboro Common (0.4 mi / 0.6 km)
  • Madame Sherri Forest (2.2 mi / 3.6 km)
  • Spofford Lake (7 mi / 11.3 km)
  • Lake Raponda (13.3 mi / 21.4 km)
  • Turner Falls (16.7 mi / 26.8 km)
  • Harriman Reservoir (17.3 mi / 27.8 km)

Seasonal weather in Brattleboro

Travellers enjoy Brattleboro for its skiing. If you're interested in winter sports, you might consider visiting in January, March, November or February, when snowfall averages 23 cm and temperatures average -3°C.

Travelling to and around Brattleboro

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

If you'd rather travel 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 holiday rental?

Among the more desired neighbourhoods to book a holiday 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 holiday rental accommodation in Brattleboro?

Houses are the most popular kind of holiday 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 holiday rental in Brattleboro?

The average price for a holiday 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 holiday home.

Are there pet-friendly holiday rentals in Brattleboro?

There are, yes. You'll have your pick of 11 holiday 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 holiday 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 holiday rentals, you'll have options to fit your style and taste, whether you're holidaying with family members, friends or even pets.

Are there large group holiday rentals in Brattleboro?

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

Are there holiday rentals in Brattleboro that welcome kids?

With 11 family-friendly holiday 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 holiday rentals in Brattleboro?

You can choose from two one-bedroom rentals in Brattleboro. Whether you'd prefer a cosy 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 holiday rentals in Brattleboro?

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

More Holiday Rentals ideas

People also search for