Photo by Shirley Rhodes

Brattleboro holiday lettings

We found 1,222 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.

Holiday rentals with weekly discounts - Brattleboro

Showing deals for:17 Oct - 24 Oct

Why visit Brattleboro

  • Outdoor Adventures: Brattleboro is perfect for skiing and various outdoor activities, surrounded by stunning lakes and lush forests.
  • Charming Atmosphere: The town boasts a friendly vibe, making it ideal for a relaxing getaway or family-friendly excursions.
  • Rich Cultural Experiences: Explore delightful neighbourhoods and local attractions that showcase the area's vibrant culture.
  • Variety of Accommodations: Choose from private holiday homes, cosy cabins, or modern condos tailored to your needs.
  • Scenic Beauty: Enjoy picturesque settings that promise an unforgettable holiday experience in the heart of Vermont.

Popular types of accommodation in Brattleboro

Brattleboro offers a delightful selection of holiday rentals, including houses, charming cabins, and modern condos. Whether you're planning a family getaway or a romantic retreat, you'll find the perfect base for your adventures. Explore our Brattleboro cabin rentals and house rentals to discover options that suit your needs. With transparency and savings at the forefront, your ideal vacation is just a click away.

  • Houses: The most sought-after choice for accommodation in Brattleboro, ideal for families or groups seeking a home-like experience.
  • Condos: A popular option for visitors, offering a blend of luxury and convenience with amenities in a communal setting.
  • Cabins: Charming retreats nestled in nature, perfect for those wanting a rustic escape.
  • Apartments: A practical choice for solo travellers or couples, providing independence in a local setting.
  • Cottages: Quaint and cosy, these rentals provide a delightful stay in a picturesque environment.**

Top attractions in and around Brattleboro

Brattleboro offers a fantastic getaway for skiing, adventure, and sports enthusiasts. With its stunning lakes, nature reserves, and lush forests, the area is perfect for those seeking outdoor activities and cultural experiences. Whether you're exploring local attractions or engaging in adventurous pursuits, Brattleboro caters to all types of travellers looking for a memorable holiday in a picturesque setting.

  • Brattleboro Common: This vibrant urban park is the heart of Brattleboro, featuring lush green spaces perfect for family picnics and leisurely strolls. Enjoy the lively atmosphere with local events and community gatherings.
  • Tasha Tudor Museum: Delve into the enchanting world of children's book illustrator Tasha Tudor. The museum showcases her art and life, offering a glimpse into her whimsical creations and deep appreciation for nature.
  • Madame Sherri Forest: Just 1.2km from Brattleboro, this stunning forest invites adventure enthusiasts to explore its scenic trails, remnants of a historic mansion, and the captivating beauty of the natural landscape.

Things to do recommended for couples

Brattleboro offers delightful experiences for couples. Enjoy live music at The Stone Church, indulge in luxury at Brattleboro Country Club, or savour the romance at Honora Winery while sampling exquisite wines. Each venue provides a unique atmosphere perfect for a memorable getaway.

Things to do recommended for families

Families will have a fantastic time at Brattleboro Bowl, an exciting arcade and adventure zone that offers a lively atmosphere perfect for all ages. Enjoy a variety of games and activities that ensure a memorable day out in the heart of Brattleboro.

Things to do recommended for groups

Explore the vibrant Brattleboro Farmers' Market, offering local produce and crafts. Enjoy a night at the Latchis Theatre, perfect for entertainment and culture. Don’t miss a visit to Delectable Mountain Cloth for unique finds, ideal for group shopping.

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming getaway? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that suits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Where to stay in and around Brattleboro

Brattleboro, Vermont, is an ideal destination for those seeking a blend of adventure and relaxation. With its charming atmosphere, friendly locals, and a plethora of outdoor activities, visitors can enjoy skiing and sports in the surrounding areas. Explore the rich culture and delightful neighbourhoods, perfect for family-friendly excursions or a tranquil retreat. Whether you’re after a cosy home for your stay or thrilling outdoor recreation, Brattleboro promises an unforgettable holiday experience.

  • Keene: Located 9.3km from Brattleboro, Keene is a vibrant city known for its stunning outdoor adventures and picturesque scenery. The area is a haven for outdoor enthusiasts, offering activities such as skiing at nearby resorts and exploring the scenic lakes and mountains that dot the landscape. Visitors can also enjoy the local charm of Keene's modern college university, which adds a youthful energy to the town. Whether you're looking to hit the slopes or simply take in the breathtaking views, Keene is an excellent choice for adventure seekers.
  • Marlboro: Nestled in the vicinity of Brattleboro, Marlboro is a quaint village perfect for those seeking a skiing and sports experience. The village is surrounded by beautiful lakes and mountains, providing a serene backdrop for outdoor activities. Skiing is a prominent attraction here, with various ski fields and resorts catering to both novices and seasoned skiers. The valley's natural beauty makes Marlboro an ideal spot for a tranquil getaway filled with adventure.
  • West Chesterfield: Just 2.5km from Brattleboro, West Chesterfield is a charming city that offers a wealth of outdoor activities, particularly for skiing enthusiasts. The area boasts stunning lakes and mountains, making it an excellent destination for those who appreciate nature and adventure. With accessible ski fields and resorts, West Chesterfield is a fantastic base for exploring the winter sports scene while enjoying the scenic beauty of the valley. A visit here promises a delightful blend of excitement and relaxation.

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 LowSlightly High
February24.4°F (-4.2°C)Light RainMostly CloudyAverageSlightly High
March32.2°F (0.1°C)Light RainMostly SunnyAverageAverage
April44.4°F (6.9°C)Light RainMostly SunnyAverageSlightly Low
May56.8°F (13.8°C)Light RainMostly SunnyAverageSlightly 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 HighSlightly 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 LowSlightly High

What do I need to keep in mind when booking a vacation in 'Brattleboro

If you're travelling with a group, family, pets, or seeking extended stays, it's essential to apply the appropriate filters to meet your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Brattleboro with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search for all of these options and more on Vrbo.
  • Traveling to Brattleboro with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming 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, a family holiday wouldn’t feel complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels at home.
  • Planning for a long term stay visiting Brattleboro: If you’re in search of holiday rentals that offer discounts for stays of a month or more, you’ve come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features such as a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform for planning your journeys, allowing you to start fresh, resume previous trips, or organise your existing plans. You can easily find properties you've saved or booked, sorted into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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:

  • Brattleboro Country Club (1.9 mi / 3 km)
  • Scott Farm Orchard (3.6 mi / 5.9 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 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.
Are there holiday rentals with WiFi in Brattleboro?
Pick from eight holiday rentals 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 Vrbo.
How can I find holiday rentals with air conditioning in Brattleboro?
Brattleboro has seven holiday rentals where you'll be able to kick back in air-conditioned comfort. To book a stay on Vrbo 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 rental in Brattleboro?
The minimum required age is typically 16, 18 or 21. It can change across properties on Vrbo, so look at the rules of your chosen Brattleboro stay before booking your trip.
How long can I rent a holiday rental in Brattleboro for?
The amount of time you can rent a Brattleboro holiday rental 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.

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