Brattleboro vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Brattleboro

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite
Bungalow in Brattleboro
Healix Luxury Getaway
This charming turn of the century cottage has been mindfully renovated with radiant floor heat and indirect lighting. The space includes vaulted ceilings, large skylight, abundant oxygen providing greenery, and high end bathroom appointments. Previously a yoga studio, it is solely an airbnb now. It's conveniently located off exit 1 on I-91, within walking distance of quaint downtown Brattleboro, with safe and free off-street parking. An entry ramp provides ease of accessibility for all.
Apr 12 – 19
$144 per night
4.93 out of 5 average rating, 228 reviews
Guest favorite
Guesthouse in Brattleboro
Light Filled Loft in the Vermont Countryside
Our spacious, tranquil, light-filled Barn Loft is thoughtfully and creatively designed. Complete with a living area, sleeping alcove, flat-screen TV, full kitchen, dining area, and large bathroom with a deluxe shower. A private deck with seating that looks out into our lovely Vermont woods and verdant gardens is attached to the loft. Stay a night or a week, there is plenty to do in every season. We are a friendly, welcoming, worldly, family. We look forward to hosting you at our country home.
Mar 25 – Apr 1
$100 per night
4.99 out of 5 average rating, 197 reviews
Superhost
Home in Brattleboro
Cozy Cabin Retreat on the River
Come stay in a recently renovated open and cozy home, walking distance to the heart of Brattleboro and right on a flowing river in an up and coming neighborhood! Everything has been updated and renovated. Gorgeous kitchen, high ceilings, memory foam beds and brand new appliances through out the house. We also have a private and peaceful fire pit with seating right on the river to relax and enjoy the beautiful outdoors. Note, there is no smoking on the property, so please respect our policy.
Apr 1 – 8
$132 per night
4.91 out of 5 average rating, 166 reviews

Popular amenities for Brattleboro vacation rentals

Stay near Brattleboro's top sights

The Marina59 locals recommend
Brattleboro Food Co-Op102 locals recommend
Whetstone Station Restaurant and Brewery116 locals recommend
The Vermont Country Deli29 locals recommend
99 Restaurants7 locals recommend
Price Chopper11 locals recommend

Other great vacation rentals in Brattleboro

Guest favorite
Home in Putney
Vermont Botanical Studio Apartment
Feb 9 – 16
$102 per night
4.94 out of 5 average rating, 330 reviews
Guest favorite
Apartment in Winchester
Downtown Loft above Winery and Distillery
Jan 31 – Feb 7
$73 per night
4.93 out of 5 average rating, 159 reviews
Guest favorite
Apartment in Marlboro
Southern Vermont Sweet Spot
Aug 15 – 22
$89 per night
4.95 out of 5 average rating, 112 reviews
Guest favorite
Guesthouse in Putney
Relax At the End of the Road
Dec 24 – 31
$108 per night
4.93 out of 5 average rating, 244 reviews
Guest favorite
Apartment in Marlboro
Shakespeare’s Folly Side Farm and AirBnB.
Feb 8 – 15
$127 per night
4.94 out of 5 average rating, 219 reviews
Guest favorite
Apartment in Putney
Hip & Cozy Storefront
Nov 14 – 21
$103 per night
4.89 out of 5 average rating, 106 reviews
Guest favorite
Apartment in Newfane
Rock River Retreat: Pets Welcome
May 21 – 28
$118 per night
4.97 out of 5 average rating, 397 reviews
Guest favorite
Cabin in Guilford
Serenity Now - Couples Retreat or Writer's Dream
Aug 3 – 10
$159 per night
4.96 out of 5 average rating, 474 reviews
Superhost
Cottage in Putney
The Cottage, a house built for guests.
Jan 10 – 15
$78 per night
4.81 out of 5 average rating, 225 reviews
Guest favorite
Barn in Chester
Inviting studio apartment above barn in Vermont
Aug 10 – 17
$88 per night
4.99 out of 5 average rating, 485 reviews
Guest favorite
Cottage in Newfane
Ridgeview: Cozy Cottage with a View
Nov 12 – 19
$121 per night
4.89 out of 5 average rating, 212 reviews
Guest favorite
Home in Guilford
Peaceful Country Home
Oct 15 – 22
$132 per night
4.94 out of 5 average rating, 173 reviews

Other great vacation rentals in Brattleboro

Guest favorite
Guest suite in Wilmington
Architectural GuestSuite
Dec 7 – 14
$103 per night
4.92 out of 5 average rating, 707 reviews
Guest favorite
Apartment in Brattleboro
Modern apartment in the heart of town!
Jul 25 – Aug 1
$180 per night
4.91 out of 5 average rating, 119 reviews
Guest favorite
Cottage in Newfane
Cozy Vermont Antique Sugar House with Fireplace
Dec 2 – 9
$135 per night
4.99 out of 5 average rating, 171 reviews
Guest favorite
Apartment in Dublin
Private Dublin apartment nestled in the woods
Mar 23 – 30
$94 per night
4.96 out of 5 average rating, 177 reviews
Superhost
Home in Putney
Spacious Loft with View
Apr 21 – 28
$146 per night
4.84 out of 5 average rating, 114 reviews
Guest favorite
Cabin in Putney
Vermont Retreat Cottage| Cozy & Romantic Escape
Sep 20 – 27
$278 per night
4.99 out of 5 average rating, 345 reviews
Guest favorite
Apartment in Brattleboro
River View apartment 30 minutes to Mt Snow.
Dec 18 – 25
$126 per night
4.99 out of 5 average rating, 69 reviews
Superhost
Cabin in Brattleboro
Solar Cabin Farmstay
May 15 – 22
$98 per night
4.93 out of 5 average rating, 46 reviews
Guest favorite
Tiny home in Brattleboro
Brattleboro Tiny House
May 26 – Jun 2
$119 per night
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Brattleboro
Beautiful one bedroom in downtown Brattleboro
Nov 6 – 13
$115 per night
4.84 out of 5 average rating, 51 reviews
Guest favorite
Home in Brattleboro
Frosted Willows
Dec 4 – 11
$168 per night
4.95 out of 5 average rating, 91 reviews
Guest favorite
Treehouse in Guilford
Cozy tent in the trees on organic flower farm
Nov 20 – 27
$111 per night
4.99 out of 5 average rating, 82 reviews

Quick stats about vacation rentals in Brattleboro

Total rentals

80 properties

Rentals with dedicated workspaces

40 properties have a dedicated workspace

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

30 properties are a good fit for families

Total number of reviews

6.1K reviews

Nightly prices starting at

$30 before taxes and fees

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Brattleboro?

    Yes! Work meets play with ease at over 40 vacation rentals in Brattleboro featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Brattleboro?

    Four-legged friends are welcome in Brattleboro. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there family-friendly apartment rentals in Brattleboro?

    Brattleboro has more than 10 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Brattleboro have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Brattleboro. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Brattleboro have a bbq area?

    Absolutely! We offer over 10 house rentals with a bbq area in Brattleboro. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Brattleboro?

    Experience the best of Brattleboro with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Brattleboro have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Brattleboro. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Brattleboro?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a bbq area, over 20 homes with wifi, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Windham County
  5. Brattleboro