Photo by Shirley Rhodes

Brattleboro holiday rentals

We found holiday rentals — enter your dates for availability

Discover a selection of 19 homes, 12 apartments 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, laundry, 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:

  • Harris Hill Ski Jump (0.7 mi / 1.2 km)
  • Brattleboro Country Club (1.9 mi / 3 km)
  • Brentwood Golf Course (15.6 mi / 25.1 km)
  • Mount Snow Golf Course (16.7 mi / 26.9 km)
  • The Hermitage Golf Club (17 mi / 27.4 km)
  • Northfield Mountain Recreation Center (17.2 mi / 27.6 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 Sherris Castle Ruins (2.1 mi / 3.4 km)
  • Madame Sherri Forest (2.2 mi / 3.6 km)
  • Spofford Lake (7 mi / 11.3 km)
  • Chesterfield Gorge Natural Area (8.9 mi / 14.3 km)
  • Hogback Mountain Conservation Area (11.9 mi / 19.2 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 home?
Among the more desired neighbourhoods to book a holiday property in Brattleboro is West Brattleboro. Find your dream stay with Stayz and experience this area like a local.
What is the most popular type of holiday home accommodation in Brattleboro?
Houses are the most popular kind of holiday home in Brattleboro, according to our data. Even if you’ve got something else in mind, Stayz has properties in all shapes and sizes. Filter our options to find your perfect match.
How much does it cost to rent a holiday home in Brattleboro?
The average price for a holiday home 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 Stayz. 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 homes in Brattleboro?
There are, yes. You’ll have your pick of 11 holiday homes that allow pets in Brattleboro on Stayz. Our furry best friends deserve a getaway too, so simply use our search function for pet-friendly holiday homes 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 Stayz, then spend leisurely days splashing about in a swimming pool that’s all yours.
What are popular home amenities in Brattleboro?
When it comes to home amenities that guests prefer in Brattleboro, nearby museums, a nearby river and a barbecue grill are at the top of the list. With Stayz holiday homes, 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 homes 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 homes in Brattleboro that welcome kids?
With 11 family-friendly holiday homes 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 homes in Brattleboro?
You can choose from two one-bedroom homes in Brattleboro. Whether you’d prefer a cosy chalet or an upmarket condo, Stayz’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 homes 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.
Are there holiday homes with WiFi in Brattleboro?
Pick from eight holiday homes with WiFi in Brattleboro. If you’d like to disconnect from the world on your holiday, but still want to be connected to the web, these getaways are just what you need. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Brattleboro?
Brattleboro has seven holiday homes where you’ll be able to kick back in air-conditioned comfort. To book a stay on Stayz offering this perk, enter your dates of travel and use the handy filters to select the “air conditioning” box.
How old do you have to be to rent a holiday home in Brattleboro?
The minimum required age is typically 16, 18 or 21. It can change across properties on Stayz, so look at the rules of your chosen Brattleboro stay before booking your trip.
How long can I rent a holiday home in Brattleboro for?
The amount of time you can rent a Brattleboro holiday home for is up to each property. Just enter your preferred travel dates to browse options offering extended stays. They have all the things you need to make your extended trip more comfortable and enjoyable, such as kitchens and backyards. Some holiday homes may also offer weekly or monthly discounts, so you can stick around for longer for less.

Explore destinations around Brattleboro

People also search for

Ski holiday rentals in Park City
Standard Link for Park City
Ski holiday rentals in Breckenridge
Standard Link for Breckenridge

More Holiday Rentals ideas

San Diego Holiday Rentals
Standard Link for San Diego
Fraser Holiday Rentals
Standard Link for Fraser
Palm Springs Holiday Rentals
Standard Link for Palm Springs
Woodstock Holiday Rentals
Standard Link for Woodstock
Killington Holiday Rentals
Standard Link for Killington
Snowmass Village Holiday Rentals
Standard Link for Snowmass Village
Stowe Holiday Rentals
Standard Link for Stowe
Aspen Holiday Rentals
Standard Link for Aspen
Alpine Holiday Rentals
Standard Link for Alpine
Melbourne Holiday Rentals
Standard Link for Melbourne
Big Sky Holiday Rentals
Standard Link for Big Sky
Kailua-Kona Holiday Rentals
Standard Link for Kailua-Kona
Carmel Holiday Rentals
Standard Link for Carmel
Vail Holiday Rentals
Standard Link for Vail
Breckenridge Holiday Rentals
Standard Link for Breckenridge
Telluride Holiday Rentals
Standard Link for Telluride
Montpelier Holiday Rentals
Standard Link for Montpelier
Anaheim Holiday Rentals
Standard Link for Anaheim
Burlington Holiday Rentals
Standard Link for Burlington
Jackson Holiday Rentals
Standard Link for Jackson
Kailua Holiday Rentals
Standard Link for Kailua
Wilson Holiday Rentals
Standard Link for Wilson
Park City Holiday Rentals
Standard Link for Park City
Honolulu Holiday Rentals
Standard Link for Honolulu
Steamboat Springs Holiday Rentals
Standard Link for Steamboat Springs
Byron Holiday Rentals
Standard Link for Byron
Yosemite National Park Holiday Rentals
Standard Link for Yosemite National Park
Laguna Beach Holiday Rentals
Standard Link for Laguna Beach