Holiday Rentals in Brattleboro, VT

46 available vacation rental offers

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Brattleboro, VT holiday rentals
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Best Holiday rentals and Airbnb offers in Brattleboro, VT

Best family friendly Brattleboro, VT holiday rentals

Among the 46 accommodations in Brattleboro, VT, here are the 4 best family friendly rentals

Mountain Viewssummer Sunsetsprivate Hiking Tailgameroomminimalist - Brattleboro, VT
10 42 reviews
Brattleboro, VT
01/07 – 22/08
SG$337/nighttotal: SG$17524 (52 )

Mountain Viewssummer Sunsetsprivate Hiking Tailgameroomminimalist

3 1
cabin , Halifax
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.
4 Br Mt Snow Okemo Ski Chalet W Amazing Views! - Brattleboro, VT
10 4 reviews
Brattleboro, VT
19/10 – 18/01
SG$309/nighttotal: SG$28119 (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.
Forest Green Retreat - Brattleboro, VT
10 1 review
Brattleboro, VT
27/06 – 04/07
SG$1264/nighttotal: SG$8848 (7 )

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.
Forest Green Retreat - Brattleboro, VT
10 4 reviews
Brattleboro, VT
26/06 – 28/06
SG$1260/nighttotal: SG$2520 (2 )

Forest Green Retreat

1 2
apartment , Brattleboro
This Brattleboro flat offers a secluded woodland setting, providing a peaceful retreat just a short drive from the town centre.
This two-bedroom flat sleeps five guests and features air conditioning, a kitchen with fridge, freezer and dishwasher, internet, parking, and a garden, making it ideal for outdoor enthusiasts and families.

Best Brattleboro, VT holiday rentals with a balcony

Clean & Convenient - Dogs Stay Free! - Brattleboro, VT
Brattleboro, VT
19/10 – 18/01
SG$431/nighttotal: SG$39221 (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.

Frequently asked questions about holiday rentals in Brattleboro, VT

Destinations nearby

Best Brattleboro, VT holiday rentals with a sauna

Tiny Birdhouse Beneath Nestled Mountainside - Brattleboro, VT
9.9 44 reviews
Brattleboro, VT
26/06 – 28/06
SG$341/nighttotal: SG$682 (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, VT holiday rentals with a fireplace

Pinecone Pond
30 Min Ski Mt Snow, 45 To Stratton - Brattleboro, VT
10 364 reviews
Brattleboro, VT
26/06 – 28/06
SG$690/nighttotal: SG$1380 (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.
Modern Apartment Close To Town - Brattleboro, VT
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.
Luxe Vt Summer Retreat: Sauna + Swimming Hole + Tiny House. Ideal For Long Stays - Brattleboro, VT
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.
Peaceful And Private Farmhouse Retreat - Brattleboro, VT
Brattleboro, VT
26/06 – 28/06
SG$581/nighttotal: SG$1162 (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.
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