Family-friendly vacation rentals in Winchester
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Winchester
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winchester family-friendly rentals
Family-friendly home rentals with a hot tub
Farm stay in Stanardsville
4.96 out of 5 average rating, 516 reviewsGreeneHouse.POOL*HotTub*MTNviews*FarmGOATS*Hiking
Cottage in Clearville
4.92 out of 5 average rating, 257 reviewsGrouseland's Vacation Cottage
Cabin in Shenandoah
4.9 out of 5 average rating, 375 reviewsRiver's Edge, perfect family spot on Shenandoah
Tiny home in Orrtanna
4.93 out of 5 average rating, 403 reviewsApple Blossom Cottage HT is extra$
Cabin in Luray
4.93 out of 5 average rating, 255 reviewsSecluded cabin with new hot tub
Home in Baker
4.97 out of 5 average rating, 290 reviewsSecluded Hilltop Retreat: Log Cabin + Hot Tub
Guesthouse in Ruckersville
4.98 out of 5 average rating, 257 reviewsMountain Guesthouse*Hot Tub*WiFi*Firepit*Grill*SNP
Home in Chester Gap
4.95 out of 5 average rating, 199 reviewsThe Nest
Family- and pet-friendly home rentals
Cottage in Gerrardstown
4.84 out of 5 average rating, 282 reviewsWooded Mountain Retreat near Creek
Cabin in Capon Bridge
4.78 out of 5 average rating, 316 reviewsWV Mountain cabin
Home in Strasburg
4.9 out of 5 average rating, 229 reviewsShenandoah Siesta
Apartment in Silver Spring
4.93 out of 5 average rating, 395 reviewsEscape to a Sunny Apartment in a Quiet D.C. Suburb
Guesthouse in Highland
4.98 out of 5 average rating, 265 reviewsWoodland Retreat
Cabin in Deep Creek
4.98 out of 5 average rating, 108 reviewsBoulder Ridge Cabin, close to Deep Creek, Maryland
Apartment in Thomas
4.99 out of 5 average rating, 472 reviewsDandy Flats - The Nonchalant
Cottage in Crozet
4.88 out of 5 average rating, 217 reviewsA-Frame Pawpaw 2 BR Cabin, Lake, Hike & Canoe
Family-friendly home rentals with a pool
Bungalow in Stanardsville
4.93 out of 5 average rating, 241 reviewsRomantic, Carriage House Studio at Fairhill Farm
Farm stay in Crozet
4.95 out of 5 average rating, 156 reviewsRefreshed '24, Mt Views & Pool: Sunset Farm Studio
Loft in Bridgewater
4.93 out of 5 average rating, 501 reviewsPrivate Studio Apt Retreat
Cabin in Culpeper
4.97 out of 5 average rating, 159 reviewsComfortable and unique 1790's log cabin
Cabin in Frostburg
4.92 out of 5 average rating, 133 reviewsBig Savage Guest Cabin
Cabin in Davis
4.78 out of 5 average rating, 447 reviewsSki Chalet Cabin Canaan Valley 35 -Dog Friendly
Cottage in Bluemont
4.95 out of 5 average rating, 204 reviewsCottage in Horse & Wine Country with Pool
Guest suite in Purcellville
4.82 out of 5 average rating, 220 reviewsMonet Suite, elegnt lrg 2rm suite/blcny in villa
Quick stats about vacation rentals that are family-friendly in Winchester
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
2.3K reviews
Nightly prices starting at
$70 before taxes and fees
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