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
31 Mar – 7 Apr
Cottage in Clearville
4.92 out of 5 average rating, 255 reviewsGrouseland's Vacation Cottage
6–13 Dec
Farm stay in Stanardsville
4.96 out of 5 average rating, 514 reviewsGreeneHouse.POOL*HotTub*MTNviews*FarmGOATS*Hiking
15–22 Nov
Home in Baker
4.97 out of 5 average rating, 289 reviewsSecluded Hilltop Retreat: Log Cabin + Hot Tub
3–10 Jun
Cabin in Shenandoah
4.9 out of 5 average rating, 373 reviewsRiver's Edge, perfect family spot on Shenandoah
21–28 Jan
Chalet in Great Cacapon
4.94 out of 5 average rating, 374 reviewsFern Haven - Waterfront Chalet w/ WiFi & Hot tub!
8–15 Dec
Cabin in Moorefield
4.94 out of 5 average rating, 411 reviewsBeautiful Log Cabin w/ Gorgeous Views & Hot Tub
14–21 Nov
Cottage in Confluence
4.82 out of 5 average rating, 129 reviewsYough Lake/Ohiopyle/ Stream Side Cottage/ Hot Tub
12–19 Jan
Family- and pet-friendly home rentals
Cabin in Luray
4.89 out of 5 average rating, 412 reviewsCozy Cabin on beautiful farmland w/ GOATS!
14–21 Oct
Cabin in Upper Tract
4.96 out of 5 average rating, 305 reviewsPotomac Overlook Log Cabin At SMOKE HOLE, WV /WIFI
30 Jan – 6 Feb
Cabin in Lost City
4.96 out of 5 average rating, 359 reviewsLog Cabin in Lost River w/ Indoor Fireplace
17–24 Oct
Guest suite in Mercersburg
4.94 out of 5 average rating, 409 reviewsThe 1780 Cabin on Main
13–20 Dec
Cabin in Luray
4.93 out of 5 average rating, 428 reviewsVista Grande, beautiful views, WiFi / pet friendly
31 Oct – 7 Nov
Chalet in Stanardsville
4.9 out of 5 average rating, 231 reviewsRiver Song Chalet - Private Retreat!
30 Sept – 7 Oct
Home in Purcellville
4.99 out of 5 average rating, 270 reviewsWhole House -Seven Elms Farm B&B
3–10 Jul
Flat in Silver Spring
4.93 out of 5 average rating, 395 reviewsEscape to a Sunny Apartment in a Quiet D.C. Suburb
11–18 Sept
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
20–27 Jun
Cottage in Bluemont
4.95 out of 5 average rating, 202 reviewsThe Cottage @ Red Gate Farm- Horse & Wine Country!
13–20 Nov
Cabin in Frostburg
4.92 out of 5 average rating, 133 reviewsBig Savage Guest Cabin
3–10 Oct
Loft in Bridgewater
4.94 out of 5 average rating, 497 reviewsPrivate Studio Apt Retreat
1–8 Sept
Bungalow in Stanardsville
4.93 out of 5 average rating, 241 reviewsRomantic, Carriage House Studio at Fairhill Farm
26 Mar – 2 Apr
Cabin in Davis
4.78 out of 5 average rating, 447 reviewsSki Chalet Cabin Canaan Valley 35 -Dog Friendly
15–22 Jan
Home in New Market
4.97 out of 5 average rating, 115 reviewsPeaceful Shenandoah Valley Getaway
21–28 Dec
Home in Oakland
4.95 out of 5 average rating, 192 reviewsPrivate|LAKE&Waterfalls|Firewood|PoolAccess|HotTub
23–30 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
2.3K reviews
Nightly prices starting at
£56 before taxes and fees
Destinations to explore
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