Family-friendly vacation rentals in Windham County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Windham County

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

Guest favorite
Home in Putney
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.
Jul 23 – 30
$81 per night
4.94 out of 5 average rating, 330 reviews
Guest favorite
Home in Readsboro
Vermont March Madness! (Pet Friendly)
Spotless, quiet, home, everything you need, exclusively yours, nestled in VT's Green Mtns, babbling brook. Great location! Winter activities, antiques, shops, lakes, hike, covered bridges, cozy dinner at local inns by a fireplace, mountain views! Enjoy Vermont! Scenic roads, Prospect Mt. or Mt. Snow, VAST trails, hiking, Mt.Greylock, Mass MOCA, in nearby N.Adams, MA, (12 min)Berkshires w/in an hour. 20 mins to Bennington & Mt. Snow. PEACEFUL & PERFECT Vermont getaway! ☺
Oct 19 – 26
$79 per night
4.86 out of 5 average rating, 118 reviews
Guest favorite
Cottage in Newfane
Ridgeview: Cozy Cottage with a View
COVID-19 NOTICE: We are open for bookings! And Vermont is a good place to be right now, and always. So you know, we observe the cleaning and safety guidelines required by the State and Air B&B. More about that upon request. At "Ridgeview" you can go to sleep to the flicker of a wood stove, wake up to sunshine streaming through tall windows onto honey-colored pine flooring, and watch from your deck as sunlight fills the river valley and plays across the ridge opposite.
Nov 20 – 27
$121 per night
4.89 out of 5 average rating, 210 reviews

Popular amenities for Windham County family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
Home in Newfane
Peaceful cabin close to skiing & Brattleboro
Feb 3 – 10
$276 per night
4.97 out of 5 average rating, 112 reviews
Guest favorite
Apartment in Townshend
Private Apt. on Farm, great views and Hot tub,
Oct 16 – 23
$135 per night
4.93 out of 5 average rating, 199 reviews
Guest favorite
Apartment in Londonderry
Vermont Getaway Apartment
Jun 19 – 26
$121 per night
4.97 out of 5 average rating, 546 reviews
Superhost
Cabin in Londonderry
The Barn private hot tub/sauna #1 Airbb S. VT
Jan 26 – Feb 2
$274 per night
4.82 out of 5 average rating, 416 reviews
Guest favorite
Home in Dover
Outdoor Paradise - Private Jacuzzi & Sauna
Sep 8 – 15
$438 per night
4.98 out of 5 average rating, 122 reviews
Guest favorite
Chalet in Dover
Grey Wolf's Den: 5 miles to Mount Snow w/HOT TUB
Mar 21 – 28
$347 per night
4.97 out of 5 average rating, 103 reviews
Guest favorite
Home in Dover
Wonderful House! Rec Room HotTub Firepit Garden!
Jul 21 – 28
$540 per night
4.97 out of 5 average rating, 75 reviews
Guest favorite
Home in Dover
Spacious Cottage 5 mins to Mount Snow
Apr 11 – 18
$288 per night
4.93 out of 5 average rating, 95 reviews
Guest favorite
Home in Jamaica
4 Bedroom on 90 Acres in the mountains of Vermont!
Jun 22 – 29
$225 per night
4.96 out of 5 average rating, 47 reviews
Superhost
Home in Peru
Norman Rockwell Spacious Contemporary + Hot Tub
Jun 5 – 12
$443 per night
4.63 out of 5 average rating, 54 reviews
Guest favorite
Home in Dover
Chalet at Triple Tree w/ Outside Hot Tub
Nov 10 – 17
$642 per night
4.91 out of 5 average rating, 35 reviews
Guest favorite
Home in Dover
PartridgeRunSkiHouse Hot Tub-3/22 Regeefest Avail
Oct 5 – 10
$850 per night
4.83 out of 5 average rating, 18 reviews

Family- and pet-friendly home rentals

Guest favorite
Home in Newfane
Adorable home in Newfane
Jan 27 – Feb 3
$121 per night
4.95 out of 5 average rating, 169 reviews
Guest favorite
Apartment in Newfane
Rock River Retreat: Pets Welcome
Oct 23 – 30
$122 per night
4.97 out of 5 average rating, 396 reviews
Guest favorite
Cottage in Jamaica
Forest Cottage ~ 7min to Stratton, Private, Views
Apr 24 – May 1
$99 per night
4.82 out of 5 average rating, 457 reviews
Guest favorite
Chalet in Dover
A charming VT chalet
Sep 21 – 28
$135 per night
4.93 out of 5 average rating, 255 reviews
Guest favorite
Cottage in Dover
Open again 5/1/24 Summer cottage in the woods
Jun 29 – Jul 6
$111 per night
4.95 out of 5 average rating, 216 reviews
Guest favorite
Loft in Wilmington
Walk to Village/Lake Whitingham
May 9 – 16
$96 per night
4.92 out of 5 average rating, 170 reviews
Superhost
Cabin in Jamaica
Green Mountain Modern House: iconic modern getaway
Aug 19 – 26
$479 per night
4.88 out of 5 average rating, 260 reviews
Guest favorite
Guesthouse in Putney
A Vermont Carriage House
Jan 20 – 27
$143 per night
4.95 out of 5 average rating, 317 reviews
Superhost
Farm stay in Marlboro
Carriage Barn - Marlboro
Sep 18 – 25
$134 per night
4.89 out of 5 average rating, 569 reviews
Guest favorite
Home in Dummerston
Pinecone Pond
Dec 9 – 16
$344 per night
4.99 out of 5 average rating, 320 reviews
Guest favorite
Home in Putney
Preston’s Pond-Beautiful home on Tranquil Hilltop
Mar 20 – 27
$151 per night
4.86 out of 5 average rating, 231 reviews
Guest favorite
Chalet in Readsboro
The King's Cottage
Jun 13 – 20
$197 per night
4.86 out of 5 average rating, 281 reviews

Family-friendly home rentals with a pool

Guest favorite
Townhouse in Dover
Bear's Den - Mt Snow Townhome w/ Ski Home Trail!
May 12 – 19
$107 per night
4.96 out of 5 average rating, 135 reviews
Guest favorite
Home in Wilmington
4 bedroom Ski House 15 min to Mount Snow
Mar 18 – 25
$176 per night
4.9 out of 5 average rating, 125 reviews
Guest favorite
Condo in Dover
Mt Snow Ski In/Out at Seasons
Apr 18 – 25
$174 per night
4.87 out of 5 average rating, 217 reviews
Guest favorite
Home in Wilmington
The Vermont Barn (Mount Snow)
Oct 28 – Nov 4
$277 per night
4.82 out of 5 average rating, 154 reviews
Guest favorite
Townhouse in Dover
Cozy Bear- 1 mile to Mt Snow Ski Home
Jun 20 – 27
$148 per night
4.93 out of 5 average rating, 71 reviews
Guest favorite
Home in West Dover
The Manor-Stunning Modern Farmhouse with Hot Tub
Apr 12 – 19
$740 per night
5.0 out of 5 average rating, 42 reviews
Guest favorite
Condo in Stratton
1st Fl Condo 3BR @ Stratton Sleeps 7 Pool Hot Tub
Mar 24 – 31
$725 per night
5.0 out of 5 average rating, 7 reviews
Guest favorite
Home in Dover
Queen Suite, Living Room, 2 TVs -Spring House 2
Apr 24 – May 1
$176 per night
4.89 out of 5 average rating, 46 reviews
Superhost
Townhouse in West Dover
MOUNT SNOW CHALET/LOFT CONDO
Mar 18 – 25
$243 per night
4.65 out of 5 average rating, 180 reviews
Guest favorite
Home in Newfane
6 BR Perfect Private Retreat in Vermont!
Mar 6 – 13
$793 per night
4.91 out of 5 average rating, 46 reviews
Superhost
Home in Londonderry
Deer Hill, With a Pool and Central HVAC system
Oct 18 – 25
$258 per night
4.83 out of 5 average rating, 53 reviews
Guest favorite
Chalet in Wilmington
Rustic Sunny Vermont Home near Mount Snow
Sep 21 – 28
$219 per night
4.94 out of 5 average rating, 89 reviews

Destinations to explore