Family-friendly holiday 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.
Holiday 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 home in Mathias
4.87 out of 5 average rating, 344 reviewsLost River Tiny House, dog-friendly + hot tub
16–23 Feb
Cottage in Clearville
4.92 out of 5 average rating, 253 reviewsGrouseland's Vacation Cottage
16–23 Jul
Farm stay in Stanardsville
4.96 out of 5 average rating, 511 reviewsGreeneHouse.POOL*HotTub*MTNviews*FarmGOATS*Hiking
15–22 Nov
Cabin in Shenandoah
4.9 out of 5 average rating, 371 reviewsRiver's Edge, perfect family spot on Shenandoah
21–28 Feb
Cabin in Luray
4.93 out of 5 average rating, 252 reviewsSecluded cabin with new hot tub
11–18 Jan
Home in Baker
4.97 out of 5 average rating, 289 reviewsSecluded Hilltop Retreat: Log Cabin + Hot Tub
19–26 Jun
Home in Chester Gap
4.95 out of 5 average rating, 196 reviewsThe Nest
16–23 Sep
Cabin in Moorefield
4.94 out of 5 average rating, 411 reviewsBeautiful Log Cabin w/ Gorgeous Views & Hot Tub
1–8 Dec
Family- and pet-friendly home rentals
Cabin in Capon Bridge
4.78 out of 5 average rating, 313 reviewsWV Mountain cabin
2–9 May
Yurt in Etlan
4.95 out of 5 average rating, 193 reviewsPeaceful Secluded Old Rag Retreat
15–22 Aug
Cabin in Lost City
4.96 out of 5 average rating, 359 reviewsLog Cabin in Lost River w/ Indoor Fireplace
1–8 Jun
Cabin in Luray
4.89 out of 5 average rating, 412 reviewsCozy Cabin on beautiful farmland w/ GOATS!
12–19 Oct
Cabin in Upper Tract
4.96 out of 5 average rating, 303 reviewsPotomac Overlook Log Cabin At SMOKE HOLE, WV /WIFI
7–14 Apr
Home in Sperryville
4.97 out of 5 average rating, 239 reviewsMountaintop Retreat
30 Jan – 6 Feb
Guest house in Highland
4.98 out of 5 average rating, 264 reviewsWoodland Retreat
18–25 Sep
Cabin in Great Cacapon
4.92 out of 5 average rating, 241 reviewsRustic Cabin on Cacapon River for Private Getaway
1–8 Jan
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!
24–31 Oct
Loft in Bridgewater
4.94 out of 5 average rating, 497 reviewsPrivate Studio Apt Retreat
13–20 Jan
Cabin in Culpeper
4.97 out of 5 average rating, 159 reviewsComfortable and unique 1790's log cabin
2–9 Jun
Bungalow in Stanardsville
4.93 out of 5 average rating, 241 reviewsRomantic, Carriage House Studio at Fairhill Farm
27 Nov – 4 Dec
Cabin in Frostburg
4.92 out of 5 average rating, 133 reviewsBig Savage Guest Cabin
8–15 Jul
Cabin in Davis
4.78 out of 5 average rating, 445 reviewsSki Chalet Cabin Canaan Valley 35 -Dog Friendly
13–20 Dec
Home in Leesburg
4.96 out of 5 average rating, 107 reviewsPotomac Overlook Farms: 6 BR, 10 Acre River Estate
25 Sep – 2 Oct
Home in Oakland
4.95 out of 5 average rating, 192 reviewsPrivate|LAKE&Waterfalls|Firewood|PoolAccess|HotTub
8–15 Jun
Quick stats about holiday 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
€ 65 before taxes and fees
Destinations to explore
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