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
Tiny homes in Mathias
4.87 out of 5 average rating, 344 reviewsLost River Tiny House, dog-friendly + hot tub
Nov. 13 – 20
Cottage in Clearville
4.92 out of 5 average rating, 253 reviewsGrouseland's Vacation Cottage
Dec. 4 – 11
Farm stay in Stanardsville
4.96 out of 5 average rating, 511 reviewsGreeneHouse.POOL*HotTub*MTNviews*FarmGOATS*Hiking
Feb. 15 – 22
Cabin in Shenandoah
4.9 out of 5 average rating, 371 reviewsRiver's Edge, perfect family spot on Shenandoah
Dec. 5 – 12
Cabin in Moorefield
4.94 out of 5 average rating, 409 reviewsBeautiful Log Cabin w/ Gorgeous Views & Hot Tub
Dec. 1 – 8
Cabin in Luray
4.93 out of 5 average rating, 252 reviewsSecluded cabin with new hot tub
Apr. 3 – 10
Chalet in Great Cacapon
4.94 out of 5 average rating, 372 reviewsFern Haven - Waterfront Chalet w/ WiFi & Hot tub!
Dec. 12 – 19
Home in Chester Gap
4.95 out of 5 average rating, 196 reviewsThe Nest
Sep. 25 – Oct. 2
Family- and pet-friendly home rentals
Cabin in Capon Bridge
4.78 out of 5 average rating, 313 reviewsWV Mountain cabin
Aug. 2 – 9
Yurt in Etlan
4.95 out of 5 average rating, 192 reviewsPeaceful Secluded Old Rag Retreat
Aug. 15 – 22
Cabin in Lost City
4.96 out of 5 average rating, 358 reviewsLog Cabin in Lost River w/ Indoor Fireplace
Jun. 1 – 8
Cabin in Upper Tract
4.96 out of 5 average rating, 303 reviewsPotomac Overlook Log Cabin At SMOKE HOLE, WV /WIFI
Mar. 2 – 9
Cabin in Luray
4.89 out of 5 average rating, 412 reviewsCozy Cabin on beautiful farmland w/ GOATS!
Sep. 9 – 16
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
Oct. 13 – 20
Cabin in Great Cacapon
4.92 out of 5 average rating, 241 reviewsRustic Cabin on Cacapon River for Private Getaway
Jan. 1 – 8
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. 13 – 20
Cabin in Culpeper
4.97 out of 5 average rating, 159 reviewsComfortable and unique 1790's log cabin
Jul. 5 – 12
Loft in Bridgewater
4.94 out of 5 average rating, 497 reviewsPrivate Studio Apt Retreat
Nov. 3 – 10
Bungalow in Stanardsville
4.93 out of 5 average rating, 241 reviewsRomantic, Carriage House Studio at Fairhill Farm
Nov. 27 – Dec. 4
Cabin in Frostburg
4.92 out of 5 average rating, 133 reviewsBig Savage Guest Cabin
Jul. 8 – 15
Townhouse in Mercersburg
4.87 out of 5 average rating, 165 reviewsResort House
Jul. 6 – 13
Chalet in McGaheysville
4.79 out of 5 average rating, 227 reviewsCozy mountainside getaway in the heart of resort
May 1 – 8
Home in Leesburg
4.96 out of 5 average rating, 107 reviewsPotomac Overlook Farms: 6 BR, 10 Acre River Estate
Oct. 31 – Nov. 7
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
$96 CAD before taxes and fees
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