Brattleboro holiday rentals: compare the best deals
10 10 reviews
Brattleboro
06/27 – 07/04
HK$2372/nighttotal: HK$16604 (7 )
Secluded Romantic Vermont Cabin With Sauna
1 2
cabin , Guilford
This luxurious Vermont lodge near Brattleboro, Guilford, offers easy access to hiking trails, swimming spots, and ski slopes within a few kilometres. The self-catering property sleeps four, featuring a queen bedroom, RV-size bunk beds, a full kitchen with an air fryer, a private porch, a shared sauna (advance booking required), and modern amenities including WiFi and smart TVs; outdoor activities include a fire pit and cornhole.
10 364 reviews
Brattleboro
06/26 – 06/28
HK$4204/nighttotal: HK$8408 (2 )
Pinecone Pond
30 Min Ski Mt Snow, 45 To Stratton
1 2
apartment , Dummerston
This charming apartment is located in southern Vermont, just 10km from Brattleboro, 15km from Putney, and within a 45-50km drive of popular ski resorts like Mt Snow and Stratton. The property enjoys an excellent user rating, with guests consistently praising the cleanliness, location and overall experience. The apartment comfortably sleeps up to six guests across multiple bedrooms and offers a fully equipped kitchen, a basement TV/rec room, and a large deck with a grill. Guests can enjoy a secluded setting with a private pond and stream, a fire pit for marshmallow roasting, and access to a washer/dryer, Wi-Fi, Roku, and a well-stocked kitchen.
10 1 review
Brattleboro
06/26 – 06/28
HK$8627/nighttotal: HK$17254 (2 )
Forest Green Retreat
1 2
house , Brattleboro
This detached house is located in a district offering convenient access to Brattleboro's attractions and outdoor pursuits. This family-friendly accommodation provides space for up to nine guests, featuring a fully equipped kitchen with a dishwasher and microwave, air conditioning, a terrace, a garden, and free private parking, with laundry service and bed linen/towels provided for a comfortable stay.
10 17 reviews
Brattleboro
10/19 – 01/18
HK$1341/nighttotal: HK$122031 (91 )
Hiking Trails On-site: Cozy Falls Brook Cabin
2 1
cabin , Dummerston
This charming cabin is located in Dummerston, Vermont, just 1.6 kilometres from the Dummerston Covered Bridge and a 10-minute drive from Brattleboro's attractions. The cabin has received excellent reviews from previous guests, highlighting its peaceful and secluded setting. This 79 square metre, two-bedroom cabin can accommodate up to four guests. The property features a fully equipped kitchen, a separate studio space, a private seasonal swimming hole, and a range of outdoor spaces for relaxation and enjoyment.
Brattleboro
10/19 – 01/18
HK$2667/nighttotal: HK$242697 (91 )
Vikings Villages Resort - Double Bed Room
1 1
chalet , Guilford
This charming Vermont lodge, near Brattleboro, offers a unique Viking-themed escape, conveniently located a short drive from attractions such as the Delectable Mountain Cloth and Brattleboro Bowl. The 60 square metre cabin sleeps four, boasting two bedrooms, a fully equipped kitchenette, a gas fireplace, and a garden; its sustainable wood construction adds to its appeal.
10 1 review
Brattleboro
07/01 – 08/22
HK$837/nighttotal: HK$43524 (52 )
Fully Furnished Two Bedroom Apartment
2 1
apartment , Brattleboro
This two-bedroom flat is situated in the heart of Brattleboro, just a short walk from the Gallery Walk and within 1.6 km of the Amtrak station. The self-catering apartment offers comfortable beds, high-speed internet, a washing machine and dryer, and dedicated off-street parking, making it perfect for families or groups of up to four people.
10 4 reviews
Brattleboro
06/26 – 06/28
HK$1050/nighttotal: HK$2100 (2 )
Vintage Cottage 5 At Brattleboro Koa
1 2
cabin , Dummerston
This updated cottage in Dummerston offers a convenient base for exploring local attractions, with the precise location detailed for easy access. This one-bedroom, one-bathroom lodge accommodates up to four guests and features year-round comfort with brand-new mini-split air conditioning and heating, high-speed WiFi, a smart TV, a mini fridge, and a propane grill for outdoor cooking.
Brattleboro
10/19 – 01/18
HK$16590/nighttotal: HK$1509690 (91 )
Every Arrival Feels Like An Exhale: Spacious 5-bedroom Estate
5 1
apartment , Winchester
This five-bedroom, four-bathroom Winchester apartment is situated in a peaceful neighbourhood, close to Schell Bridge and the Old NMH Campus Building #3. The property sleeps six guests and boasts a modern design, including a microwave, dishwasher, air conditioning, parking, and is ideal for photoshoots, workshops or small gatherings near Winchester Speedpark and The Stone Church.
8.6 7 reviews
Brattleboro
10/19 – 01/18
HK$1403/nighttotal: HK$127673 (91 )
Year Round Mountain Retreat
2 1
apartment , Brookline
This charming cabin is located in Newfane, Vermont, a 30-minute drive from Brattleboro and a short walk from the Putney mountain trailhead, offering a peaceful escape from the hustle and bustle of Brookline. The property has received very good user ratings, indicating a positive experience for previous guests. The cabin is suitable for up to four guests and features two bedrooms and two bathrooms. Guests can enjoy a range of amenities, including a garden, parking, internet access, and a wood-burning stove, as well as the opportunity to explore nearby hiking trails, cheese farms, and ski resorts.
10 1 review
Brattleboro
10/19 – 01/18
HK$2943/nighttotal: HK$267813 (91 )
Shagbark,a Rock River Retreat,3 Bd+den,2.5ba On 14.5 Private Acres In Newfane Vt
4 1
apartment , Newfane
This Newfane holiday home is situated within easy reach of Rock River Preserve, just a 13-minute walk away, and a mere 6-minute drive from Manitou. This spacious 242 square metre apartment accommodates up to 8 guests with 4 bedrooms and 3 bathrooms, featuring a fully equipped kitchen, air conditioning, Wi-Fi, and on-site parking, as well as outdoor barbecue facilities.
9.9 429 reviews
Brattleboro
06/26 – 06/28
HK$1450/nighttotal: HK$2900 (2 )
~Serene Barn Retreat~
1 2
apartment , Dummerston
This one-bedroom barn apartment is located in Dummerston, just 800 metres from the West River Trail, which leads to Brattleboro's Marina, and is surrounded by the peaceful countryside of the Nature Conservancy. The apartment has received excellent ratings for cleanliness, location and user experience. The apartment can accommodate up to three guests and features a kitchen with a fridge, parking and internet access. Guests can also enjoy shared amenities such as a communal kitchen, a clawfoot tub, and access to all common outdoor areas, perfect for relaxing and enjoying the natural surroundings.
9.3 3 reviews
Brattleboro
07/01 – 08/22
HK$837/nighttotal: HK$43524 (52 )
Perfect For The Traveling Professional
2 1
apartment , Brattleboro
This two-bedroom flat is situated in a quiet residential area of Brattleboro, just a short walk from the town centre and within easy reach of the Connecticut River and the Brattleboro Museum & Art Center. The apartment has received excellent ratings for cleanliness and location, with guests describing it as a very good option for exploring the town. The flat is fully furnished and can comfortably accommodate two guests. It includes a private patio, dedicated parking, and a private washer and dryer, making it a convenient and comfortable base for exploring the area.
Best family friendly Brattleboro holiday rentals
Among the 46 accommodations in Brattleboro, here are the 4 best family friendly rentals
10 3 reviews
Brattleboro
10/19 – 01/18
HK$1654/nighttotal: HK$150514 (91 )
Wellness Getaway With A Personal Sauna, And Private River Beach!
1 1
cabin , Newfane
This charming cabin is located just 19 kilometres from Brattleboro, 40 kilometres from Grafton, and 48 kilometres from Bellows Falls, making it a great base for exploring the beautiful Vermont countryside. The cabin has received excellent reviews from previous guests, highlighting its peaceful and tranquil setting. The cabin has one bedroom and one bathroom, comfortably accommodating up to two guests. Guests can enjoy a private river beach, a sauna, a garden, and a kitchen with a fridge and microwave oven, as well as a range of wellness services, a daily breakfast, and a nightly happy hour.
10 13 reviews
Brattleboro
10/19 – 01/18
HK$3140/nighttotal: HK$285740 (91 )
Luxury Rural Stay Close To Town
3 1
apartment , Guilford
This riverfront property is situated in Guilford, just 10km from attractions like the Tasha Tudor Museum, Brattleboro Farmers' Market, and Creamery Covered Bridge, offering a peaceful retreat close to local highlights. Guests have consistently rated this home excellent, highlighting its comfortable and convenient features. The house has three bedrooms and three bathrooms, comfortably accommodating up to nine guests. Enjoy the convenience of a fully equipped kitchen, a patio, a garden, and a tennis court for your leisure, all within a smoke-free environment.
10 3 reviews
Brattleboro
07/01 – 08/22
HK$726/nighttotal: HK$37752 (52 )
Fully Furnished 2br Apartment
1 1
apartment , Brattleboro
This fully furnished flat is located in the heart of downtown Brattleboro, just a short walk from shops, restaurants, and cultural attractions. It has received excellent ratings for location, cleanliness, and overall user experience. The apartment offers a spacious and comfortable living space with a queen-sized bed, perfect for a couple or small family of three. Guests can enjoy access to a fully equipped kitchen, high-speed Wi-Fi, a shared laundry, and off-street parking, making it an ideal choice for longer stays.
10 4 reviews
Brattleboro
10/19 – 01/18
HK$1886/nighttotal: HK$171626 (91 )
4 Br Mt Snow Okemo Ski Chalet W Amazing Views!
4 1
apartment , Marlboro
This Vermont lodge, situated between Wilmington and Brattleboro, is under 32km from Mount Snow ski resort, offering easy access to both towns and their amenities. Sleeping up to 10 guests in four bedrooms and three bathrooms, the property boasts a fully equipped kitchen (fridge, microwave, dishwasher), Wi-Fi, parking, and a large deck with stunning Vermont hill views; nearby attractions include the Southern Vermont Natural History Museum and Hogback Mountain Conservation Area.
Best Brattleboro holiday rentals with a balcony
9.6 321 reviews
Brattleboro
10/19 – 01/18
HK$1200/nighttotal: HK$109200 (91 )
Family Friendly Hilltop House In Putney Vermont
2 1
apartment , Putney
This charming lakeside house in Putney, Vermont is perfectly situated within a 3-mile radius of Harlow's, Next Stage Arts, and Landmark College, offering easy access to local attractions. The property has received excellent ratings for location, cleanliness, and overall experience. The 158 square metre house comfortably accommodates up to 6 guests in its two bedrooms and two bathrooms. The home boasts a host of amenities, including a fully equipped kitchen, laundry facilities, a spacious balcony, a garden, a spa, parking, and a playground for children.
Brattleboro
10/19 – 01/18
HK$2625/nighttotal: HK$238875 (91 )
Clean & Convenient - Dogs Stay Free!
3 1
apartment , Brattleboro
This three-bedroom holiday flat in Brattleboro offers convenient access to the Connecticut River, a mere 3-minute drive away, and is within walking distance of the Harris Hill Ski Jump (700 metres) and the Estey Organ Museum (1.1 kilometres). This accommodation for six guests provides essential amenities including Wi-Fi and air conditioning, with nearby attractions such as Epsilon Spires, Creamery Covered Bridge, Brattleboro Country Club, Winchester Speedpark, and The Stone Church concert venue offering diverse recreational and cultural opportunities.
This three-bedroom Vermont lodge is situated near Jacksonville, approximately 9.6km from Honora Winery and various state parks, including H.O. Cook State Forest and Molly Stark State Park. Sleeping seven, the property boasts a fully equipped kitchen, fireplace, private garden, terrace, and on-site arcade; guests can also enjoy free Wi-Fi and parking.
Frequently asked questions about holiday rentals in Brattleboro
What sports or outdoor activites can visitors enjoy in and around Brattleboro, VT?
Brattleboro is a great place for outdoor enthusiasts. You can go hiking in the Green Mountain National Forest, kayaking on the Connecticut River, or skiing at nearby Mount Snow. There are also plenty of opportunities for fishing, swimming, and rock climbing.
What are the best Airbnb and vacation rentals in Brattleboro?
What other towns or cities can be easily accessed from Brattleboro, VT?
Brattleboro is conveniently located near several other towns and cities. You can easily drive to Keene, New Hampshire, or Bennington, Vermont, both of which are about 40 km away. A little further afield, you can also visit Northampton, Massachusetts, which is about 80 km away.
What amenities are commonly available in vacation rentals in Brattleboro, VT?
Vacation rentals in Brattleboro often come with amenities like Wi-Fi, laundry facilities, and parking. Many also have kitchens, fireplaces, and outdoor spaces. You can find rentals that cater to different needs, from cozy studios to spacious houses.
What are the best rentals for families and kids in Brattleboro?
What time of year is best to rent a vacation rental Brattleboro, VT?
The best time to visit Brattleboro depends on your interests. If you enjoy warm weather and outdoor activities, summer is ideal. Autumn is beautiful with its vibrant foliage, while winter is perfect for skiing and snowboarding. Spring offers a pleasant mix of mild weather and blooming flowers.
What are the best rentals or Airbnbs with a jacuzzi in Brattleboro?
What are the local dishes in Brattleboro, VT region?
Brattleboro has a vibrant culinary scene with a focus on local and seasonal ingredients. You can find delicious farm-to-table dishes at restaurants like The Whetstone and The Common Ground. Be sure to try Vermont maple syrup, cheese, and craft beer, which are all local specialties.
Destinations nearby
Best Brattleboro holiday rentals with a sauna
9.9 44 reviews
Brattleboro
06/26 – 06/28
HK$2081/nighttotal: HK$4162 (2 )
Tiny Birdhouse Beneath Nestled Mountainside
1 2
cabin , Brattleboro
This guest house is located in Brattleboro, just a short distance from the town centre and with views of Round Mountain and a nearby pond. The accommodation has received excellent ratings for its cleanliness, location and user experience. The property features a private deck with views of the surrounding countryside and can accommodate up to two guests. Guests can enjoy a daily continental breakfast, access to a hot tub and sauna, and complimentary high-speed internet.
Best Brattleboro holiday rentals with a fireplace
Brattleboro
06/26 – 06/28
HK$3542/nighttotal: HK$7084 (2 )
Peaceful And Private Farmhouse Retreat
1 2
apartment , Chesterfield
This rural retreat, a detached house, is situated on over 121 hectares of conserved land just outside Chesterfield, New Hampshire, approximately 16 kilometres from Brattleboro, Vermont, and 24 kilometres from Keene, New Hampshire. This property accommodates up to seven guests and features a well-equipped kitchen with a fridge, freezer, microwave, and dishwasher, air conditioning, two bathrooms, and garden access, with nearby attractions including Chesterfield Gorge Natural Area and Pisgah State Park, offering opportunities for hiking, skiing and wildlife observation.
9.4 6 reviews
Brattleboro
10/19 – 01/18
HK$3859/nighttotal: HK$351169 (91 )
Beautiful Vermont Country Home On Vast Property
5 1
apartment , Marlboro
This five-bedroom house in Brattleboro is ideally located just a short drive from the Southern Vermont Natural History Museum and Molly Stark State Park. The property has received excellent ratings for its location, cleanliness, and overall experience. The spacious house can comfortably accommodate up to 10 guests, making it perfect for families or groups of friends. Guests can enjoy a fully equipped kitchen, a garden, a barbecue, free Wi-Fi, and a DVD player, as well as convenient parking.
10 41 reviews
Brattleboro
07/01 – 08/22
HK$771/nighttotal: HK$40092 (52 )
Recharge In A Yurt At Rest Farm Campground
1 1
yurt , Hinsdale
This yurt is located just across the road from the Kilburn entrance to Pisgah State Park, bordering Bear Mountain Park, offering easy access to over 14,000 hectares of hiking trails. The surrounding area is peaceful and tranquil, despite the proximity to the road. This one-bedroom, two-bathroom yurt can comfortably accommodate two guests. The property offers showers and bathrooms for guests, and is conveniently located near hiking trails, making it ideal for nature enthusiasts seeking a secluded escape.
Brattleboro
07/01 – 08/22
HK$667/nighttotal: HK$34684 (52 )
Modern Apartment Close To Town
1 1
apartment , Dummerston
This modern two-bedroom flat is located in Dummerston, just 2.4 kilometres from the town of Brattleboro, offering a peaceful setting surrounded by 15 acres of woods and gardens. It is part of a historic home dating back to 1854, adding a touch of history to its modern design. The flat has a spacious open-plan layout and can comfortably accommodate up to six guests. Enjoy the outdoors with a deck featuring a fire pit and a covered seating area, as well as convenient off-road parking.