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
Cottage in Clearville
4.92 out of 5 average rating, 255 reviewsGrouseland's Vacation Cottage
16–23 Jul
Farm stay in Stanardsville
4.96 out of 5 average rating, 513 reviewsGreeneHouse.POOL*HotTub*MTNviews*FarmGOATS*Hiking
13–20 Nov
Home in Baker
4.97 out of 5 average rating, 289 reviewsSecluded Hilltop Retreat: Log Cabin + Hot Tub
1–8 Jun
Chalet in Great Cacapon
4.94 out of 5 average rating, 374 reviewsFern Haven - Waterfront Chalet w/ WiFi & Hot tub!
8–15 Dec
Home in Chester Gap
4.95 out of 5 average rating, 196 reviewsThe Nest
28 Oct – 4 Nov
Cabin in Moorefield
4.94 out of 5 average rating, 411 reviewsBeautiful Log Cabin w/ Gorgeous Views & Hot Tub
4–11 Oct
Cabin in Shenandoah
4.9 out of 5 average rating, 372 reviewsRiver's Edge, perfect family spot on Shenandoah
15–22 Oct
Cabin in Berkeley Springs
4.93 out of 5 average rating, 469 reviewsHorizon Hill - Log Cabin w/Hot Tub & Views!
28 Jul – 4 Aug
Family- and pet-friendly home rentals
Cabin in Capon Bridge
4.78 out of 5 average rating, 314 reviewsWV Mountain cabin
11–18 Oct
Yurt in Etlan
4.95 out of 5 average rating, 193 reviewsPeaceful Secluded Old Rag Retreat
23–30 Oct
Cabin in Luray
4.89 out of 5 average rating, 412 reviewsCozy Cabin on beautiful farmland w/ GOATS!
15–22 Oct
Cabin in Lost City
4.96 out of 5 average rating, 359 reviewsLog Cabin in Lost River w/ Indoor Fireplace
5–12 Feb
Cabin in Upper Tract
4.96 out of 5 average rating, 304 reviewsPotomac Overlook Log Cabin At SMOKE HOLE, WV /WIFI
23–30 Nov
Cabin in Stanley
4.89 out of 5 average rating, 238 reviewsThe Bavarian Inn at Shenandoah River
16–23 Jul
Home in Sperryville
4.97 out of 5 average rating, 239 reviewsMountaintop Retreat
24–31 Jan
Guest house in Highland
4.98 out of 5 average rating, 264 reviewsWoodland Retreat
18–25 Oct
Family-friendly home rentals with a pool
Cabin in Culpeper
4.97 out of 5 average rating, 159 reviewsComfortable and unique 1790's log cabin
23–30 Jun
Cottage in Bluemont
4.95 out of 5 average rating, 202 reviewsThe Cottage @ Red Gate Farm- Horse & Wine Country!
10–17 Oct
Bungalow in Stanardsville
4.93 out of 5 average rating, 241 reviewsRomantic, Carriage House Studio at Fairhill Farm
23–30 Oct
Cabin in Davis
4.78 out of 5 average rating, 446 reviewsSki Chalet Cabin Canaan Valley 35 -Dog Friendly
2–9 Dec
Cabin in Frostburg
4.92 out of 5 average rating, 133 reviewsBig Savage Guest Cabin
31 Aug – 7 Sep
Loft in Bridgewater
4.94 out of 5 average rating, 497 reviewsPrivate Studio Apt Retreat
1–8 Aug
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 reviewsLAKE&Waterfalls|Private|Firewood|PoolAccess|HotTub
4–11 Apr
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
2.3T reviews
Nightly prices starting at
₹5,835 before taxes and fees
Destinations to explore
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