Brattleboro Vacation Rentals

Our Favorite Vacation Rentals in Brattleboro

  • Tentrr - Hillside Camp in Southern Vermont
     Country House
    Booking.com
    From
    $83
  • Church sanctuary
     3br Home/Apartment
    HolidayLettings
    From
    $326
  • Wilmington Hideaway
     Country House
    Booking.com
    From
    $189
  • Bright three-level home w/water views, jetted tub, firepit, and more!
     2br Home/Apartment
    HolidayLettings
    From
    $533
  • Log Cabin Escape
     Country House
    Booking.com
    From
    $323
  • Charming, rural house w/shared tennis, private Ping-Pong table, Foosball, & more
     4br Home/Apartment
    HolidayLettings
    From
    $381
  • Lakeside Year Round Totally Renovated Home
     5br Home/Apartment
    HolidayLettings
    From
    $1,391
  • Apartment with a view
    ExcellentHome/Apartment
    Airbnb
    From
    $102

Check prices for these upcoming dates

Brattleboro Vacation Rentals with a Pool

  • Spacious Apt, Walk to Town. WIFI and Washer/dryer
    Good2br Home/Apartment
    Airbnb
    From
    $172
  • Mt. Snow/Stratton Estate 100 Acres
    Excellent7br Home/Apartment
    Airbnb
    From
    $2,783
  • Gorgeous Mountain Top Estate with Swimming Pool
    Excellent6br Estate
    Airbnb
    From
    $1,808

Brattleboro Vacation Rentals with Wi-Fi

  • Maple St Guest Room, Brattleboro VT
    ExcellentHome/Apartment
    Airbnb
    From
    $63
  • Cozy & Comfy Tiny House, HeartStorm Farmstead
    ExcellentHome/Apartment
    Airbnb
    From
    $133
  • Quiet, Cozy & Great location for exploring VT !
    ExcellentHome/Apartment
    Airbnb
    From
    $92
  • Cozy 19th-century home in town
    ExcellentFarmhouse
    Airbnb
    From
    $73

Brattleboro Pet-Friendly Vacation Rentals

  • Secluded Hideaway Minutes to Town & Ski Areas
    Excellent5br Cabin
    Airbnb
    From
    $315
  • Tiny Art House - Free Spa Pass* - Dogs Welcome!
    ExcellentHome/Apartment
    Airbnb
    From
    $92
  • The Studio With a View, bring your dog, too!
    ExcellentHome/Apartment
    Airbnb
    From
    $141
  • Mountain Island
    Excellent2br Home/Apartment
    Airbnb
    From
    $236

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

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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
61° -3°
7
62°
3
58° -22°
4
74° -6°
4
60°
3
72° 16°
3
90° 35°
1
94° 40°
5
102° 45°
6
94° 52°
8
92° 42°
7
83° 21°
3
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

This climate histogram shows you the weather patterns in Brattleboro. The warmest months in Brattleboro are June and July, when temperatures reach 102 ˚F. The coolest month is December, when temperatures drop to -22 ˚F. The wettest month in Brattleboro is May with 8.06 inches of rain, while the driest month is August with 0.8 inches of rain.

What Expert Travelers Think

  • — I love that AllTheRooms has everything in one place when I need to find accommodations that fit my family. Plus it provides all the details I need to help me make the best choice. I often recommend AllTheRooms to friends and family visiting NYC and they agree that it’s a great. Such a time saver!

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  • — 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!

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    Laurelle McVickerLaurelle McVicker
  • — When I first opened up the AllTheRooms.com site, I was impressed right away... When I’m traveling, I don’t like to waste time searching multiple engines for accommodations, it gets overwhelming and frustrating fast. I want a unique, comfortable stay for the best deal

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Vacation Rentals in Brattleboro

Browse accommodations from all the leading providers including Airbnb, Priceline, Bed and Breakfast and others at AllTheRooms.com. Brattleboro has 300 hotels, vacation rentals and other unique places to stay, with prices to suit careful travellers, extravagant travelers and everything in between. A trip to Brattleboro can be affordable - the cheapest price rental is available at $19 a night. On average, an accommodation in Brattleboro will cost you $103 per night.

If you need to stay connected during your trip, then you can choose from over 112 accommodations in Brattleboro that have WiFi. 38 of our accommodations include a breakfast in the price. Choose from 15 places to stay that provide gym options, so you don't miss a single workout. If you're planning on arriving in Brattleboro by car, be sure to choose from 115 accommodations that provide parking. 17 hotels and vacation rentals have a a pool or jacuzzi

Those traveling with a dog, cat or some other animal can stay in one of 24 accommodations that are designated as pet-friendly.

AllTheRooms compares vacation rentals, hotels and other bespoke accommodation types from many providers in Brattleboro, including 113 places to stay from Airbnb, 5 accommodations from Priceline and 4 places to stay from Bed and Breakfast

167 accommodations in Brattleboro have been reviewed; 80% are rated excellent or good. 63 accommodations allow instant booking.

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