Brattleboro holiday rentals

We found 1,289 holiday rentals — enter your dates for availability
Discover a selection of 28 homes, 10 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:18 Dec - 25 Dec

Two story living room with 70" smarttv, premium directtv and bluetooth turntable
Terrace/patio
Sun or snow, it's quite the show
Exterior
Exceptional
(10 reviews)

HotTub&GameRm&Traeger Smoker-15 min 2 Mt Snow, Across from Golf, 5 min to Lake

Wilmington

16% off
AU$11,953
for 7 nights, 1 chalet
AU$1,708 per night
includes taxes & fees
HotTub&GameRm&Traeger Smoker-15 min 2 Mt Snow, Across from Golf, 5 min to Lake
Property grounds
Large living room with endless natural light
New custom kitchen
Exterior
Exceptional
(17 reviews)

Private 6 bedroom Chalet 5min to Mt Snow

West Dover

8% off
AU$16,199
for 7 nights, 1 chalet
AU$2,314 per night
includes taxes & fees
Private 6 bedroom Chalet 5min to Mt Snow
Private kitchen
Living area
Terrace/patio
Dining
Exceptional
(35 reviews)

Beautiful log home close to Mt. Snow with hot tub and sauna.

West Dover

8% off
AU$12,682
for 7 nights, 1 cabin
AU$1,812 per night
includes taxes & fees
Beautiful log home close to Mt. Snow with hot tub and sauna.
Enjoy chess, checkers or backgammon
A beautiful brook that runs through our lot
Master 2 Second Floor
Summer view from the lake
Exceptional
(101 reviews)

New Lakefront Log Home

Wilmington

12% off
AU$5,896
for 7 nights, 1 chalet
AU$842 per night
includes taxes & fees
New Lakefront Log Home
Private kitchen
Interior
View from upstairs guest room
Primary bedroom balcony
Exceptional
(8 reviews)

Views of Stratton, Minutes from the Slopes, EV Charging Level 2

Bondville

8% off
AU$15,692
for 7 nights, 1 home
AU$2,242 per night
includes taxes & fees
Views of Stratton, Minutes from the Slopes, EV Charging Level 2
Dining area, 10 Chairs are now black, Need a new picture!
View out front door
Open Kitchen with a wide open feel
Early morning summer view
Exceptional
(243 reviews)

Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews

Wilmington

8% off
AU$8,157
for 7 nights, 1 home
AU$1,165 per night
includes taxes & fees
Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews
Livingroom with a view.
Front of the house
King bed
Patio chairs and solo stove firepit
Exceptional
(16 reviews)

Chalet Mount Snow/Stratton Skiing/hiking

East Dover

8% off
AU$4,713
for 7 nights, 1 chalet
AU$673 per night
includes taxes & fees
Chalet Mount Snow/Stratton Skiing/hiking
Private kitchen
Interior
Room
Dining
Exceptional
(79 reviews)

Western Mountain Lodge on River and Close to Stratton

Jamaica

17% off
AU$24,447
for 7 nights, 1 home
AU$3,492 per night
includes taxes & fees
Western Mountain Lodge on River and Close to Stratton
Living area with wood stove.
Kitchen and dining area.
Enjoy the infamous Moss Rock!
Living area with wood stove
Exceptional
(26 reviews)

Vermont ski chalet near beautiful Mount Snow and the quaint town of Wilmington

West Dover

8% off
AU$5,530
for 7 nights, 1 chalet
AU$790 per night
includes taxes & fees
Vermont ski chalet near beautiful Mount Snow and the quaint town of Wilmington
View of the Main house living room from the kitchen bar
Main house top floor river room with sounds of the river out the windows.
Main house top floor river room with deck overlooking the pool and backyard.
View of the main house from the creek on the property.
Exceptional
(38 reviews)

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Wardsboro

8% off
AU$22,156
for 7 nights, 1 home
AU$3,165 per night
includes taxes & fees
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Front door
Living area
Dining room
Back porch
Exceptional
(40 reviews)

Wishing Well Cabin

Jamaica

8% off
AU$3,775
for 7 nights, 1 cabin
AU$539 per night
includes taxes & fees
Wishing Well Cabin
Terrace/patio
Large open-concept living and kitchen area
3-Season porch (new addition 2023)
Dining area
Exceptional
(18 reviews)

Leonard’s Log Cabin— Mt. Snow/Stratton Ski House

Wardsboro

8% off
AU$8,634
for 7 nights, 1 cabin
AU$1,233 per night
includes taxes & fees
Leonard’s Log Cabin— Mt. Snow/Stratton Ski House
Antique Cabin
Porch -Summer
Exterior
Porch - Winter
Exceptional
(89 reviews)

Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton

Jamaica

8% off
AU$5,997
for 7 nights, 1 home
AU$857 per night
includes taxes & fees
Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton
Living area
Exterior
Private kitchen
Games room
Exceptional
(39 reviews)

Beautiful Four Season Family Vacation Home

West Dover

12% off
AU$10,775
for 7 nights, 1 home
AU$1,539 per night
includes taxes & fees
Beautiful Four Season Family Vacation Home
Dining
Exterior
Private kitchen
Plenty of room for relaxing.
Exceptional
(33 reviews)

Winterfell chalet - quiet, relaxing & private with Stratton on your doorstep.

Bondville

8% off
AU$9,247
for 7 nights, 1 chalet
AU$1,321 per night
includes taxes & fees
Winterfell chalet - quiet, relaxing & private with Stratton on your doorstep.
main level living room area
Jacuzzi hot tub
main level living room sitting area
foyer for all skiing and outdoor stuff
Exceptional
(26 reviews)

True Vermont Log Cabin Home at Mount Snow

West Dover

8% off
AU$9,505
for 7 nights, 1 cabin
AU$1,358 per night
includes taxes & fees
True Vermont Log Cabin Home at Mount Snow
Private kitchen
Interior
Dining
Exterior
Exceptional
(6 reviews)

Grateful Getaway - 5BR, 3.5B Home Sleeps 10 - Close to Mount Snow!

Wilmington

8% off
AU$10,519
for 7 nights, 1 home
AU$1,503 per night
includes taxes & fees
Grateful Getaway - 5BR, 3.5B Home Sleeps 10 - Close to Mount Snow!
Interior
Indoor spa tub
Dining
Games room
Exceptional
(53 reviews)

SKIING, PARTY SAFELY IN THE SNOW! NO NEED TO DRINK & DRIVE.

Wilmington

8% off
AU$11,257
for 7 nights, 1 home
AU$1,608 per night
includes taxes & fees
SKIING, PARTY SAFELY IN THE SNOW! NO NEED TO DRINK & DRIVE.
Loft with surround sound Entertainment
Living area
Kitchen and dining Area - seats 9 with bench / 2 at counter
Dining
Exceptional
(32 reviews)

Perfect Get-Away House - 6 Miles from Stratton & Mount Snow

West Wardsboro

5% off
AU$8,786
for 7 nights, 1 home
AU$1,255 per night
includes taxes & fees
Perfect Get-Away House - 6 Miles from Stratton & Mount Snow
View of dining/kitchen area from entrance landing.
View from deck.
Kitchen and dining area.
Living area
Exceptional
(25 reviews)

Spacious/Elegant 3 level house on Spruce Lake- swim or fish, short drive to Mt.

Wilmington

18% off
AU$7,406
for 7 nights, 1 home
AU$1,058 per night
includes taxes & fees
Spacious/Elegant 3 level house on Spruce Lake- swim or fish, short drive to Mt.
Outdoor firepit with plenty of seating
Open floorplan
downtown is just a 4 minute walk. So much to see and do
Fully stocked kitchen with gas range
Exceptional
(11 reviews)

Large rustic home with gameroom. Near lakes, skiing, walk to downtown.

Wilmington

12% off
AU$9,699
for 7 nights, 1 home
AU$1,386 per night
includes taxes & fees
Large rustic home with gameroom. Near lakes, skiing, walk to downtown.
Living Room
Property grounds
Exterior
Private kitchen
Exceptional
(20 reviews)

Cozy Vermont Home Near Mount Snow & Stratton

West Wardsboro

8% off
AU$5,495
for 7 nights, 1 home
AU$785 per night
includes taxes & fees
Cozy Vermont Home Near Mount Snow & Stratton
Exterior
Outdoor dining
Property grounds
Living area
Exceptional
(31 reviews)

Secluded large country home for big groups with giant open yard for outdoor fun.

Whitingham

20% off
AU$3,540
for 7 nights, 1 home
AU$506 per night
includes taxes & fees
Secluded large country home for big groups with giant open yard for outdoor fun.
Hallway view from the bathroom looking toward the kitchen area.
Owner and guest parking. Private guest access is located through the porch door.
A small kitchenette fully equipped for small-scale cooking.
Room
Exceptional
(35 reviews)

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Stamford

8% off
AU$1,380
for 7 nights, 1 apartment
AU$197 per night
includes taxes & fees
Getaway Near Mass MoCA, Great Hiking, Scenic Views

  • 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:

  • 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)
  • The Hermitage Club (18.2 mi / 29.4 km)
  • Mount Snow (19.8 mi / 31.9 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)
  • Hogback Mountain Conservation Area (11.9 mi / 19.2 km)
  • Lake Raponda (13.3 mi / 21.4 km)
  • Jacksonville Pond (13.7 mi / 22 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?
One of the best areas to consider for a holiday rental in Brattleboro is the downtown district. This vibrant area offers a charming atmosphere with its historic architecture and a delightful array of shops, cafes, and restaurants. Staying here puts you within walking distance of top attractions such as the Brattleboro Museum & Art Centre, where you can explore contemporary art exhibitions, and the iconic Latchis Theatre, a beautifully restored art deco cinema that hosts a variety of performances and films.Another appealing neighbourhood is West Brattleboro, known for its scenic views and a more tranquil setting. Here, you can enjoy the natural beauty of the Connecticut River and take advantage of outdoor activities like hiking and biking. This area also has a selection of properties, often featuring larger spaces, making it a great choice for families or groups looking for a peaceful retreat.
Where are the best Brattleboro ski resort rentals?
For ski resort rentals near Brattleboro, Vermont, the closest major ski area is Mount Snow, located approximately 30 minutes away. In the town of Dover, just a short drive from Mount Snow, travellers can find a range of rental properties, including spacious chalets and cosy cabins that cater to various group sizes. Many of these accommodations come equipped with essential amenities such as full kitchens, living areas with fireplaces, and access to outdoor decks that provide stunning views of the surrounding mountains.In addition to Dover, the nearby village of Wilmington offers additional options for holiday rentals. Here, visitors can discover charming homes that often feature traditional New England architecture, along with modern conveniences like hot tubs, ski storage, and laundry facilities. The proximity to local shops and restaurants enhances the overall experience, allowing guests to easily explore the culinary scene after a day on the slopes.For those looking for a more rustic experience, there are also cabins in the nearby Green Mountain National Forest, which can provide a serene escape, often with amenities like wood-burning stoves and outdoor fire pits.
What is the most popular type of holiday rental accomodation in Brattleboro?
In Brattleboro, holiday houses are the most popular type of holiday rental, with around 68 available throughout the area. These homes typically offer spacious layouts, fully equipped kitchens, and outdoor spaces—ideal for families or groups looking to enjoy the natural beauty of Vermont. Additionally, approximately 40 apartments are scattered across the town, providing a more compact option for travellers who prefer a homely atmosphere without the need for extensive space. Many of these apartments come with modern amenities, comfortable living areas, and convenient locations near local shops and dining options. There are also a dozen cabins, alongside several chalets and cottages, which cater to those seeking a more rustic experience.
Are there any family house rentals in Brattleboro?
In Brattleboro, Vermont, there are numerous family-friendly house rentals available, with about 14 options to choose from. This charming town is known for its picturesque landscapes and vibrant arts scene, making it an excellent destination for families. Properties often feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces for children to play. Many homes are equipped with amenities such as Wi-Fi and laundry facilities, ensuring a comfortable stay for visitors.Families can explore nearby attractions like the Brattleboro Museum & Art Centre or take a stroll along the scenic Connecticut River. The local parks, such as Living Memorial Park, offer playgrounds and picnic areas, great for a day out with the kids.
Can I rent a holiday home with a pool or hot tub in Brattleboro?
In Brattleboro, there are several holiday homes available for rent that feature pools and hot tubs, making it a great choice for those seeking relaxation. This charming town, located in the picturesque Green Mountains, offers a variety of neighbourhoods where these properties can be found. Many rentals come equipped with private pools, hot tubs, and spacious outdoor areas, ideal for enjoying the scenic surroundings. Inside, travellers can expect amenities such as fully equipped kitchens, comfortable living spaces, and Wi-Fi, ensuring a pleasant stay.
Are there pet-friendly house rentals in Brattleboro?
In Brattleboro, there are several pet-friendly house rentals available, with a variety of options to suit different needs. Many of these properties come equipped with modern amenities, such as fully stocked kitchens, spacious living areas, and outdoor spaces where pets can enjoy fresh air.The downtown area offers charming homes that are within walking distance of local shops and restaurants, making it convenient for travellers who wish to explore the vibrant community. Additionally, the nearby Retreat Farm provides a lovely outdoor space for pets to roam, with walking trails and beautiful views of the surrounding hills.For those seeking a more rural experience, there are rentals in the outskirts of Brattleboro, often featuring larger yards and serene surroundings. These homes typically offer amenities like fireplaces and porches, superb for relaxing after a day of outdoor adventures.
Are there any remote work holiday rentals in Brattleboro?
In Brattleboro, Vermont, there are plenty of remote work holiday rentals available, with around 108 options to choose from. This charming town, located along the Connecticut River, offers a serene environment conducive to productivity. Many properties come equipped with reliable Wi-Fi, ensuring that you can stay connected while working remotely.Travellers can expect various amenities such as dedicated workspaces, comfortable seating, and plenty of natural light, which are ideal for creating an inspiring work atmosphere. Additionally, some rentals allow events, providing flexibility for meetings or small gatherings.Brattleboro is also known for its vibrant arts scene, local markets, and beautiful outdoor spaces, making it a great spot to unwind after work. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Brattleboro?
In Brattleboro, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many properties also offer onsite parking, which is particularly convenient for those driving to the area. For those looking to enjoy the outdoors, rentals often feature decks or patios, providing a lovely space to relax and take in the surroundings. Additionally, some accommodations permit pets, making it easier for travellers to bring their furry friends along. Many rentals also provide coffee and tea makers, ensuring guests can enjoy a warm beverage at their leisure.
When is the best time to visit Brattleboro for a holiday rental?
July marks the peak season in Brattleboro, Vermont, drawing visitors eager to enjoy the warm summer weather and vibrant community events. This lively month is superb for those who appreciate outdoor activities, as the area offers splendid opportunities for hiking and exploring the scenic beauty of the Green Mountains.From July to September, tourists flock to Brattleboro to partake in various festivals and local markets. The climate during this time is typically pleasant, with temperatures ranging from the low 20s to mid-30s Celsius, making it ideal for leisurely strolls along the Connecticut River or exploring the charming downtown area filled with quaint shops and cafés.For travellers seeking a more budget-friendly experience, November presents an excellent opportunity. While this month is quieter, it offers a unique charm as the autumn foliage transitions into a serene winter landscape. Plus, you can enjoy the peaceful atmosphere while discovering the local art scene or indulging in the delightful cuisine without the crowds.Ultimately, your choice of when to visit Brattleboro should reflect your personal preferences.
What are the top attractions in Brattleboro?
In Brattleboro, visitors can enjoy a range of attractions that showcase the town's vibrant culture and natural beauty. The historic downtown area is home to unique shops, art galleries, and the renowned Brattleboro Museum & Art Centre, which often features exhibitions by local and national artists. The iconic Whetstone Brook runs through the town, providing scenic views and opportunities for strolls along the riverbanks.For those who appreciate nature, the nearby Retreat Farm offers walking trails, farm animals, and seasonal events, creating a family-friendly atmosphere. The area also boasts the stunning Fort Dummer State Park, where outdoor enthusiasts can explore hiking trails and enjoy picnicking amidst the lush surroundings.Additionally, the local food scene is thriving, with various eateries offering farm-to-table dining experiences, making it a delightful destination for food lovers. The annual Strolling of the Heifers festival is another highlight, celebrating local agriculture and community spirit.
Are all fees included in the Brattleboro holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Brattleboro holiday homes with parking?
Stayz offers a wide selection of holiday homes in Brattleboro with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Brattleboro holiday homes?
You can find great discounts on holiday homes in Brattleboro on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Brattleboro holiday home booking on Stayz?
To find Brattleboro holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Brattleboro?
A long-stay holiday home in Brattleboro is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Brattleboro holiday home?
Book your Brattleboro holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Brattleboro?
Prices for holiday homes in Brattleboro vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Brattleboro to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

More holiday ideas