Best Holiday rentals and Airbnb offers in Brattleboro, VT
9.6 5 reviews
Brattleboro, VT
01/07 – 22/08
SG$151/nightTotal: SG$7852 (52 )
Fully Furnished Two Bedroom Apartment
2 1
apartment , Brattleboro
This two-bedroom apartment is situated in a renovated building in a central Brattleboro district, just a short walk from the downtown area and the Connecticut River. It has received excellent ratings for its cleanliness, location, and overall experience, making it an ideal choice for travellers. The apartment is spacious and comfortably accommodates up to four guests. It comes fully furnished, with modern amenities such as a washer and dryer, and offers a peaceful retreat after a day exploring the town.
9.6 91 reviews
Brattleboro, VT
03/09 – 06/09
SG$334/nightTotal: SG$1002 (3 )
Beautiful One Bedroom In Downtown Brattleboro
1 4
apartment , Brattleboro
This charming guesthouse is located in the heart of Brattleboro, just a 0.2 km walk from Main Street, restaurants, shops, galleries, and the train station. The accommodation has been consistently rated excellent for its location, cleanliness, and overall experience. The property offers a comfortable bedroom, a queen-size air mattress, a twin-size air mattress, and a comfortable couch, accommodating up to four guests. It also features a private deck with a grill, an outdoor fire pit, and a movie theater rental for evenings spent relaxing and enjoying the peaceful ambiance.
Brattleboro, VT
01/07 – 22/08
SG$2723/nightTotal: SG$141596 (52 )
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.
10 1 review
Brattleboro, VT
01/07 – 22/08
SG$137/nightTotal: SG$7124 (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.
9.9 427 reviews
Brattleboro, VT
03/09 – 06/09
SG$292/nightTotal: SG$876 (3 )
~Serene Barn Retreat~
1 4
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.
9.7 26 reviews
Brattleboro, VT
01/07 – 22/08
SG$416/nightTotal: SG$21632 (52 )
Green Mountain Oasis!
1 1
apartment , Brattleboro
This eco-boutique apartment is situated in Southern Vermont, 9.6km from Brattleboro town centre and a 40-minute drive from Mount Snow ski resort. The self-catering flat offers a queen-sized bed, fully equipped kitchen, and access to on-site winter activities including a toboggan run, skating pond, and cross-country skiing trails, accommodating up to two guests.
Brattleboro, VT
01/07 – 22/08
SG$109/nightTotal: SG$5668 (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.
10 41 reviews
Brattleboro, VT
01/07 – 22/08
SG$127/nightTotal: SG$6604 (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.
9.9 341 reviews
Brattleboro, VT
03/09 – 06/09
SG$332/nightTotal: SG$996 (3 )
Apt In Town 2 Br/2 Levels In Victorian Farmhouse
1 4
apartment , Brattleboro
This two-bedroom flat is located just 0.2 kilometres from Brattleboro’s Main Street, putting you within easy walking distance of the town's theatre, art scene, and restaurants. The property has received excellent ratings for its location, cleanliness, and overall experience. The flat is fully equipped for a comfortable stay, with a kitchen, living room, and bathroom, accommodating up to four guests. You can enjoy modern amenities such as Apple TV, a flat-screen TV, and WiFi, as well as access to a shared terrace, gardens, and laundry facilities.
Brattleboro, VT
01/07 – 22/08
SG$250/nightTotal: SG$13000 (52 )
Airstream Mountainside With Pond
1 1
cabin , Brattleboro
This Airstream trailer is located in a retreat centre, just 50 metres from a private bathroom, and is situated in Brattleboro, Vermont. The retreat centre offers a peaceful and tranquil setting, perfect for a relaxing getaway. The Airstream is a unique accommodation option, perfect for couples or solo travellers. The trailer includes a microwave and mini-fridge, a hot tub, sauna, and a dining room/sunroom. Guests also have access to a continental breakfast and a fitness centre.
9.9 162 reviews
Brattleboro, VT
03/09 – 06/09
SG$482/nightTotal: SG$1446 (3 )
Modern Apartment In The Heart Of Town!
1 4
apartment , Brattleboro
This one-bedroom flat is located on Main Street in downtown Brattleboro, just a short walk from the Brattleboro Food Coop and within easy reach of numerous shops, restaurants, and cafes. The apartment has received excellent ratings for cleanliness, location, and overall experience. The flat is on the second floor and can comfortably accommodate up to four guests. It features a well-equipped kitchen with a fridge, microwave oven, and dishwasher, as well as air conditioning and internet access. Guests can enjoy the lively atmosphere of Main Street from the apartment's window and are within walking distance of Mount Wantastiquit, a scenic hiking destination.
9.9 204 reviews
Brattleboro, VT
03/09 – 06/09
SG$284/nightTotal: SG$852 (3 )
Contemporary Forest Eco-retreat, Mountain Views
1 4
apartment , Brattleboro
This one-bedroom flat is situated on a hillside just 3 kilometres outside Brattleboro, offering a peaceful retreat in a forested area, with easy access to the town centre and the Connecticut River. It has consistently received excellent ratings for its location, cleanliness, and overall experience. The apartment has a private entrance and a lush garden, providing a secluded feel, and can comfortably accommodate up to four guests. Enjoy stunning mountain views, a modern kitchen with an induction hob and quartz worktops, high-speed internet, and a private laundry area.
Best family friendly Brattleboro, VT holiday rentals
Among the 46 accommodations in Brattleboro, VT, here are the 4 best family friendly rentals
9.9 28 reviews
Brattleboro, VT
03/09 – 06/09
SG$704/nightTotal: SG$2112 (3 )
Kipling's Carriage House
1 4
apartment , Dummerston
This Dummerston dwelling, situated on a 45-acre plot a few minutes' drive from Brattleboro and Interstate 91, shares a driveway with the historic Naulakha, Rudyard Kipling's former home. The two-bedroom, one-bathroom property sleeps four, offering a fully equipped kitchen, games room, fireplace, private clay tennis court (June-November – Vermont's first!), and ample opportunities for hiking and cross-country skiing on its extensive grounds.
10 1 review
Brattleboro, VT
03/09 – 06/09
SG$1331/nightTotal: SG$3993 (3 )
Forest Green Retreat
1 4
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.
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.
10 3 reviews
Brattleboro, VT
01/07 – 22/08
SG$119/nightTotal: SG$6188 (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.
Best Brattleboro, VT holiday rentals with a balcony
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.
10 1 review
Brattleboro, VT
03/09 – 06/09
SG$1331/nightTotal: SG$3993 (3 )
Forest Green Retreat
1 4
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.
Frequently asked questions about holiday rentals in Brattleboro, VT
What other towns or cities can be easily accessed from Brattleboro, VT?
Brattleboro is a great base for exploring the region. You can easily reach Bennington, Vermont, Northampton, Massachusetts, and Keene, New Hampshire, all within a one-hour drive. Each town offers its own unique charm and attractions.
What are the best Airbnb and vacation rentals in Brattleboro, VT?
What amenities are commonly available in vacation rentals in Brattleboro, VT?
Vacation rentals in Brattleboro usually offer a range of amenities, including Wi-Fi, laundry facilities, and parking. Many also have kitchenettes or full kitchens, fireplaces, and outdoor space. Some rentals even have hot tubs or swimming pools.
What are the most popular Airbnbs in Brattleboro, VT?
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.
Best Brattleboro, VT holiday rentals with a fireplace
9.8 588 reviews
Brattleboro, VT
03/09 – 06/09
SG$270/nightTotal: SG$810 (3 )
Mahalo Temple Retreat
1 4
house , Brattleboro
This unique octagonal house is located just 3.2 kilometres from the centre of Brattleboro, Vermont, offering a peaceful retreat in a secluded setting off Route 9. The house has received excellent ratings for its cleanliness, location, and overall experience. This unusual property is ideal for a family of up to four guests, featuring a comfortable futon and floor mats for sleeping. The house is equipped with everything you need for a comfortable stay, including a wood-burning stove, air conditioning, a garden and ample parking.
8.0 1 review
Brattleboro, VT
01/07 – 22/08
SG$267/nightTotal: SG$13884 (52 )
Luxe Vt Summer Retreat: Sauna + Swimming Hole + Tiny House. Ideal For Long Stays
3 1
apartment , Newfane
This Newfane dwelling offers a secluded riverside escape in Southern Vermont, situated approximately 400 kilometres from both NYC and Boston, adjacent to a scenic mountain river within a wooded environment. This modern 2-bedroom, 2-bathroom property includes a separate tiny house, accommodating up to four guests, and features private river beach access, a wood-fired sauna, outdoor cooking facilities, and a firepit, ideal for remote workers with fast WiFi and extended summer stays.
9.8 103 reviews
Brattleboro, VT
01/07 – 22/08
SG$192/nightTotal: SG$9984 (52 )
Modern Vermont Farm Stay
1 1
gîte , Brattleboro
This charming cottage is located on a working farm just 5 kilometres outside of downtown Brattleboro, Vermont, offering a tranquil escape from the hustle and bustle of town. It has received excellent ratings for its cleanliness, location, and user experience. The self-catering cottage has one bedroom and one bathroom, comfortably sleeping two guests. It offers a fully equipped kitchen, a cosy fireplace, a spacious garden, and parking, as well as access to nearby hiking trails, boating opportunities, other farms, and golf courses.