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
Cabin in Front Royal
4.89 out of 5 average rating, 158 reviews♛Royal A-Frame♛HOT TUB★PetsOK★WoodStove★FASTwifi
May 2 – 9
Cottage in Clearville
4.92 out of 5 average rating, 253 reviewsGrouseland's Vacation Cottage
Dec 3 – 10
Farm stay in Stanardsville
4.96 out of 5 average rating, 511 reviewsGreeneHouse.POOL*HotTub*MTNviews*FarmGOATS*Hiking
Dec 23 – 30
Cabin in Shenandoah
4.9 out of 5 average rating, 371 reviewsRiver's Edge, perfect family spot on Shenandoah
Feb 15 – 22
Cabin in Moorefield
4.94 out of 5 average rating, 409 reviewsBeautiful Log Cabin w/ Gorgeous Views & Hot Tub
Jan 31 – Feb 7
Cabin in Luray
4.93 out of 5 average rating, 252 reviewsSecluded cabin with new hot tub
Apr 2 – 9
Tiny home in Orrtanna
4.93 out of 5 average rating, 402 reviewsApple Blossom Cottage HT is extra$
Nov 24 – Dec 1
Home in Chester Gap
4.95 out of 5 average rating, 196 reviewsThe Nest
Sep 18 – 25
Family- and pet-friendly home rentals
Cabin in Capon Bridge
4.78 out of 5 average rating, 313 reviewsWV Mountain cabin
Jan 24 – 31
Yurt in Etlan
4.95 out of 5 average rating, 192 reviewsPeaceful Secluded Old Rag Retreat
Aug 15 – 22
Place to stay in Bentonville
4.98 out of 5 average rating, 387 reviewsJohn Pope Cabin Browntown Va. We now have Starlink
Aug 30 – Sep 6
Cabin in Luray
4.89 out of 5 average rating, 411 reviewsCozy Cabin on beautiful farmland w/ GOATS!
Jul 7 – 14
Cabin in Upper Tract
4.96 out of 5 average rating, 303 reviewsPotomac Overlook Log Cabin At SMOKE HOLE, WV /WIFI
Mar 20 – 27
Place to stay in The Plains
4.94 out of 5 average rating, 162 reviewsThe Whistle Stop
Dec 24 – 31
Home in Sperryville
4.97 out of 5 average rating, 239 reviewsMountaintop Retreat
Apr 3 – 10
Cabin in Stanley
4.89 out of 5 average rating, 238 reviewsThe Bavarian Inn at Shenandoah River
Jul 31 – Aug 7
Family-friendly home rentals with a pool
Cottage in Bluemont
4.95 out of 5 average rating, 202 reviewsThe Cottage @ Red Gate Farm- Horse & Wine Country!
Dec 2 – 9
Cabin in Culpeper
4.97 out of 5 average rating, 159 reviewsComfortable and unique 1790's log cabin
Jul 10 – 17
Loft in Bridgewater
4.94 out of 5 average rating, 497 reviewsPrivate Studio Apt Retreat
Jan 12 – 19
Cabin in Frostburg
4.92 out of 5 average rating, 133 reviewsBig Savage Guest Cabin
Sep 3 – 10
Townhouse in Mercersburg
4.87 out of 5 average rating, 165 reviewsResort House
May 5 – 12
Home in Leesburg
4.96 out of 5 average rating, 107 reviewsPotomac Overlook Farms: 6 BR, 10 Acre River Estate
Sep 24 – Oct 1
Home in New Market
4.96 out of 5 average rating, 114 reviewsPeaceful Shenandoah Valley Getaway
Dec 6 – 13
Home in Harpers Ferry
4.87 out of 5 average rating, 178 reviewsThe Historic Booth House at the Harpers Ferry KOA
Nov 25 – Dec 2
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
G$14,606 GYD before taxes and fees
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