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Family-friendly vacation rentals in Brattleboro

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Brattleboro

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Farm stay in Marlboro

4.89 out of 5 average rating, 577 reviews

Carriage Barn - Marlboro

Our place is within easy reach of Mt Snow, Carinthia, Marlboro Music Festival, and the super sweet town of Brattleboro. The 2-level apartment is entirely private and self-contained. Bonus offerings include an abundance of fresh country air and proximity to miles of woods trails. It's ideal for couples, solo travelers, and it's pet-friendly too. A short walk through the woods brings you to a spring-fed lake that is quiet and pristine. Winter, spring, summer, fall. Each season has its own magic.

Dec 25 – Jan 1

G$33,795 GYD per night

Cabin in Brattleboro

4.95 out of 5 average rating, 130 reviews

Peaceful rural cabin on beautiful large property

Surrounded by acres of protected land, but only 15 mins to downtown Brattleboro shops, restaurants, farmers market, galleries & theaters. Cozy, private, sunny, year-round two bedroom cabin with large eat-in kitchen, comfortable living room with gas fireplace & sweeping views of fields, woods, streams and distant Mt Monadnock. Wonderful deck & large private yard. Walks & snowshoeing/x-country skiing nearby. Downhill skiing is 35 minutes away at Mount Snow. Near renowned Marlboro Music Festival.

May 13 – 20

G$33,573 GYD per night

Guesthouse in Brattleboro

4.99 out of 5 average rating, 199 reviews

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.

Jul 8 – 15

G$27,496 GYD per night

Home in Putney

4.94 out of 5 average rating, 339 reviews

Vermont Botanical Studio Apartment

This room is one half of a floor in our studio building (35 sq m). It is the only occupied space in the building, which is separated from the main house by a yard. There is a queen-sized bed, full bath (no-curb shower), and an outdoor shower (not available in the winter) Small kitchen with a sink, fridge, 2-burner induction hob, microwave/convection oven, toaster, coffee pot, and cookware. Arched ceiling, with ceiling fan, large windows, deck, and Maggie's botanical art lining the walls.

Dec 19 – 26

G$22,397 GYD per night

Home in West Brattleboro

4.86 out of 5 average rating, 125 reviews

Cozy Home for 2-5 People in Vermont

Comfortable house for 2 to 4 people (two queen-sized beds) and a pull-out couch for a 5th person and a self-inflatable bed. Located in a quiet neighborhood. There are two main bedrooms with queen beds in each. There is also a pull-out couch in the room with the fireplace though it is not as comfortable as the self-inflatable bed (and deflatable) in the house. Fast Wi-Fi from Xfinity. Easy to get into Brattleboro Center and an excellent location for exploring Southern Vermont.

Jan 31 – Feb 7

G$37,891 GYD per night

Guest suite in Wilmington

4.92 out of 5 average rating, 713 reviews

Architectural GuestSuite

The Guest Suite is located on the first floor of an architectural studio in historic Wilmington, Vermont. Please enjoy the piano, drums, and art supplies! The Guest Suite is both UNIVERSALLY ACCESSIBLE, TOBACCO FREE, and ANIMAL FREE due to allergies in our family. LineSync Architecture staff will be working from 8:30am - 5ish upstairs, and once in a while on the weekends. When guests are in we try to be super sensitive and quiet, but footsteps will be heard!

Aug 22 – 29

G$24,593 GYD per night

Cabin in Warwick

4.97 out of 5 average rating, 194 reviews

Artsy Pine Cabin in the Woods

Come relax in our private and cozy one room cabin tucked in the woods on the family homestead. A peaceful location for connecting with nature, writing & hiking. It's a 12'x16' cabin, with a comfortable queen size bed, electricity, mini refrigerator and electric kettle. Water is provided. Equipped with a clean outhouse and an outdoor hot shower on side of main house. ( May use indoor shower in main house in cooler months) Excellent spot for star gazing.

May 9 – 16

G$18,581 GYD per night

Apartment in Brattleboro

4.96 out of 5 average rating, 284 reviews

Apt in town 2 BR/2 levels in Victorian Farmhouse

We're two blocks from Main Street and it's just a few blocks more to the local theater, art and culture, a variety of excellent restaurants, and walking trails. You’ll love my place because we're so close to town, but not on a main through street, so it's quiet here. My place is good for couples, or a group of friends, solo adventurers, traveling professionals, and for a great get-away.

Jun 12 – 19

G$31,018 GYD per night

Apartment in Newfane

4.97 out of 5 average rating, 406 reviews

Rock River Retreat: Pets Welcome

You are welcome here with fresh air & room to run - your pet, too, when registered as an extra person! Your private guest suite awaits in a 1790's colonial on the Rock River in the quiet village of South Newfane, VT. Note: Recent floods in Vermont have thankfully not affected our home or guest experience. ❤️ PLEASE READ THE ENTIRE DESCRIPTION BELOW re: kitchenette & pet details.

Nov 20 – 27

G$27,266 GYD per night

Cabin in Brattleboro

4.89 out of 5 average rating, 442 reviews

Cottage

The "Rustic" cottage is furnished with a queen bed, sofa and dining table. There is a small deck with patio furniture, fire ring with wood supplied, and a gas barbecue. It can accommodate 2 people comfortably. Private with parking. Host in separate house. Wi Fi from Xfinity, but please note that it can be patchy. Roku TV WI FI connected to router.

Jun 14 – 21

G$27,535 GYD per night

Apartment in Marlboro

4.95 out of 5 average rating, 112 reviews

Southern Vermont Sweet Spot

Abundantly sunny apartment tucked away in the hills of Southern VT. Rolling field with lovely southern views. Rural, peaceful spot on a dirt road. 6-8 minutes from Marlboro College, 20 minutes from Brattleboro, and 30 minutes from Mount Snow. Marlboro is a wonderful place to explore, with many local trails and wooded spots.

Jun 3 – 10

G$19,423 GYD per night

Home in Putney

4.95 out of 5 average rating, 308 reviews

Cozy Train Depot in Putney Vermont

Charming and cozy 1 bedroom house in Putney, Vermont. A former train depot, this home is just a few minutes walk to the Connecticut River with boat launch for enjoying fishing, swimming, canoeing and kayaking. Or curl up in the window seat and enjoy the fire!

Jun 30 – Jul 7

G$27,732 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Apartments

Convenient locations with everyday essentials

Popular amenities for Brattleboro family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Home in Newfane

4.97 out of 5 average rating, 115 reviews

Peaceful cabin close to skiing & Brattleboro

Apr 9 – 16

G$64,651 GYD per night

Apartment in Townshend

4.94 out of 5 average rating, 203 reviews

Private Apt. on Farm, great views and Hot tub,

Oct 17 – 24

G$32,192 GYD per night

Cottage in Shaftsbury

4.99 out of 5 average rating, 599 reviews

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

Jan 23 – 30

G$90,796 GYD per night

Home in Chester

4.96 out of 5 average rating, 311 reviews

Riverfront Getaway

Oct 14 – 21

G$38,249 GYD per night

Home in Colrain

4.94 out of 5 average rating, 155 reviews

Secluded Farmhouse Retreat - stunning views

Oct 25 – Nov 1

G$71,436 GYD per night

Cabin in Londonderry

4.82 out of 5 average rating, 421 reviews

The Honeymoon Barn - hot tub/sauna #1 Airbb S. VT

Aug 5 – 12

G$66,189 GYD per night

Bungalow in Easthampton

4.92 out of 5 average rating, 431 reviews

The Creation Station

Jul 21 – 28

G$35,809 GYD per night

Home in Shaftsbury

4.93 out of 5 average rating, 122 reviews

Converted Vermont Barn on 6.5 acres with hot tub

Nov 14 – 21

G$45,425 GYD per night

Family- and pet-friendly home rentals

Home in Newfane

4.95 out of 5 average rating, 171 reviews

Adorable home in Newfane

Mar 31 – Apr 7

G$28,941 GYD per night

Tiny home in Jamaica

4.88 out of 5 average rating, 345 reviews

Forest Cabin ~ 7min to Stratton, Cozy, Private

May 6 – 13

G$17,587 GYD per night

Guesthouse in Putney

4.95 out of 5 average rating, 322 reviews

A Vermont Carriage House

Dec 14 – 21

G$35,120 GYD per night

Guesthouse in Springfield

4.86 out of 5 average rating, 321 reviews

Connecticut River-Cozy Cottage

Nov 22 – 29

G$19,098 GYD per night

Guest suite in Montague

4.93 out of 5 average rating, 163 reviews

Great Falls Private Suite

Sep 22 – 29

G$20,802 GYD per night

Tiny home in Jamaica

4.94 out of 5 average rating, 1145 reviews

Apple Blossom Cottage: A Tiny House

Aug 6 – 13

G$31,536 GYD per night

Guest suite in Charlemont

4.9 out of 5 average rating, 182 reviews

Unique People & Pet-Welcoming Haven

Mar 7 – 14

G$22,383 GYD per night

Chalet in Dover

4.93 out of 5 average rating, 265 reviews

A charming VT chalet

Oct 14 – 21

G$32,221 GYD per night

Family-friendly home rentals with a pool

Guesthouse in Granville

4.9 out of 5 average rating, 786 reviews

Moon Valley Country Retreat no clean fee pets yes

Dec 6 – 13

G$22,165 GYD per night

Guesthouse in Williamstown

4.93 out of 5 average rating, 219 reviews

Perfect Base for Your Berkshire Adventure

Jun 16 – 23

G$24,044 GYD per night

Farm stay in Rutland

4.97 out of 5 average rating, 318 reviews

Farm Living

Jan 12 – 19

G$30,197 GYD per night

Bungalow in Williamstown

4.89 out of 5 average rating, 202 reviews

Hollywood Bungalow in the Berkshires

Nov 24 – Dec 1

G$49,014 GYD per night

Condo in Killington

4.77 out of 5 average rating, 282 reviews

Serene Killington Condo (resort style amenities)

Jul 24 – 31

G$26,700 GYD per night

Condo in Hancock

4.83 out of 5 average rating, 131 reviews

Cozy Condo @ Jiminy Peak

Mar 19 – 26

G$33,735 GYD per night

Apartment in Northampton

4.96 out of 5 average rating, 200 reviews

Wood, sunshine & movies in best downtown location

Aug 2 – 9

G$72,495 GYD per night

Home in Wilmington

4.83 out of 5 average rating, 155 reviews

The Vermont Barn (Mount Snow)

Jan 27 – Feb 3

G$85,596 GYD per night

Quick stats about vacation rentals that are family-friendly in Brattleboro

Total rentals
30 properties
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Total number of reviews
1.8K reviews
Nightly prices starting at
G$6,275 GYD before taxes and fees

Destinations to explore