Brattleboro Vacation Rentals

Check prices for these upcoming dates

Brattleboro Travel Guide

The artistic and musical capital of Southern Vermont, Brattleboro is a lively community of highly creative and outgoing individuals. Brattleboro features miles upon miles of mountain roads, a variety of galleries, cafes, and boutiques, as well as charming vacation rentals.

Things to Do in Brattleboro

Converging in downtown Brattleboro, the West River and Connecticut River offer Brattleboro’s visitors a variety of fun outdoor activities such as kayaking, fishing, swimming, tubing, and canoeing. Visitors can also spend the day hiking and biking through the woodlands and forests of the Retreat Trails, camping in Fort Drummer State Park, and cycling with Vermont Cycling Tours. Guests wanting to spend some time indoors can enjoy a tour of the Etsey Organ Museum or Tasha Tudor Museum, play a game of bowling at the Brattleboro Bowl, or challenge themselves to climb the highest watt at BrattCave, Brattleboro’s only indoor rock climbing gym. For visitors 21+, a visit to Windham Wines can be a good way to spend the day, as the location offers wine tastings and great customer service.

Best Places to Stay in Brattleboro

There are a variety of both short term and long term vacation rentals in Brattleboro. They are located all over the city and most are within walking distance of the city’s many amenities, making them ideal for busy families and couples looking to have a fun weekend away. From some of the more rural vacation homes, visitors can enjoy a scenic view of Stratton Mountain.

Best Time to Visit Brattleboro

The best time for a visit to Brattleboro is May through September when the weather is warm and ideal for outdoor activities.

Best Events in Brattleboro

A few of the best and most well-known events in Brattleboro include the Brattleboro Film Festival, Brattleboro Brewer’s Guide, Yellow Barn Music Festival, Tiny House Fest Vermont, and Winter Carnival. The Winter Carnival includes a host of live entertainment such as jugglers, music, actors, and comedians, tasty food, and child-friendly activities.

Things to Do for Families in Brattleboro

Families with members of all ages can enjoy a day at Retreat Farm. Retreat Farm offers visitors the chance to pet and feed a variety of farm animals including sheep and goats. It also allows them to take fun classes like goat yoga, go hiking on the trails surrounding the retreat, and learn all about the creatures found within the barns and stables. In the winter, Fair Winds Farms is a great place to go for a family sleigh ride, while the Brattleboro Museum and Art Center is a great all year-round destination, featuring an impressive collection of modern art and a variety of exciting, rotating featured exhibits.

Price and Availability in Brattleboro

Most expensive
Most availability
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
The cheapest day to stay at a vacation rental in Brattleboro tends to be Tuesday, while the most expensive day tends to be Friday. Vacation homes in Brattleboro tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Brattleboro is in September, while the cheapest month is in March. The most popular time to book a vacation rental in Brattleboro is in the high season in August. Brattleboro has its low season in April, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Brattleboro

Rainy days
68° -2°
1
77° 17°
4
84° 30°
3
88° 36°
5
95° 50°
3
87° 40°
2
86° 34°
2
76° 26°
5
70°
3
52° -8°
4
54° -11°
4
59° -10°
2
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Rainy days

This climate histogram shows you the weather patterns in Brattleboro. The warmest months in Brattleboro are June and July, when temperatures reach 95 ˚F. The coolest month is December, when temperatures drop to -11 ˚F. The wettest month in Brattleboro is March with 5.33 inches of rain, while the driest month is October with 0.95 inches of rain.

What Expert Travelers Think

  • — Site is easy to use; clean, laid out well, good colors and branding, fun logo and title that connects to the purpose of the brand. The blog, vacation destinations, and rental destinations is a great feature and really make the brand stand apart from other sites!

    Laurelle McVicker
    Laurelle McVickerLaurelle McVicker
  • — Packed full of information, from the best time of year to visit (I love NYC in Spring) to top tips from locals, All The Rooms provides the best accommodation, whether you are looking to enjoy your first time visit to New York or want to experience a new location

    Jaz
    JazThe Life of a Social Butterfly
  • — Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options

    Sarah Pool
    Sarah PoolTammymum

Vacation Rentals in Brattleboro

Pick the perfect accommodation for your trip at AllTheRooms.com. We compare Airbnb, Priceline, Agoda and many more. AllTheRooms has 256 vacation rentals, hotels and other great places to stay while you enjoy Brattleboro, with everything from cheap hostels and homestays to extravagant Airbnbs and hotels. A vacation in Brattleboro can be budget-friendly - our cheapest price vacation rental is available at $15 a night. The average price of a vacation rental is $107 per night.

Those looking to get some work done during their trip to Brattleboro can choose from 121 places to stay that provide WiFi. 31 places to stay include a breakfast. You can keep up with your workout regime by staying at one of 17 accommodations that provide gym facilities. If you're planning on getting to Brattleboro by car, be sure to choose from 121 accommodations that provide parking. We have 20 places to stay that have a pool or jacuzzi.

Those traveling with a cat, dog or some other animal can stay in one of 27 accommodations that are designated as pet-friendly.

AllTheRooms aggregates vacation rentals, hotels and other bespoke accommodation types from loads of providers in Brattleboro, including 112 places to stay from Airbnb, 14 accommodations from Priceline and 4 places to stay from Agoda

157 of our accommodations in Brattleboro have been reviewed and rated. 80% are rated great. You can instantly book any of 59 places to stay right now.

Destinations near Brattleboro

  • Killington3,189 Properties
  • Stowe2,499 Properties
  • Ludlow1,571 Properties
  • Warren979 Properties
  • Dover895 Properties
  • Burlington644 Properties
  • Smugglers Notch466 Properties
  • Wilmington452 Properties
  • Waitsfield422 Properties
  • Woodstock300 Properties
  • Jamaica273 Properties
  • Plymouth268 Properties
  • Stratton Mountain235 Properties
  • Jay232 Properties
  • Middlebury230 Properties
  • Rutland204 Properties
  • Londonderry202 Properties
  • Manchester200 Properties
  • Bennington199 Properties
  • Montpelier199 Properties
  • Colchester195 Properties
  • South Hero193 Properties
  • Morrisville178 Properties
  • Waterbury165 Properties
  • East Burke157 Properties
  • Arlington137 Properties