Pet-friendly holiday rentals in Winchester
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Winchester
Guests agree: these pet-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 pet-friendly home rentals
Pet-friendly house rentals
Home in Strasburg
4.9 out of 5 average rating, 229 reviewsShenandoah Siesta
Home in Bolivar
4.96 out of 5 average rating, 189 reviewsNewly renovated - Walk to Harpers Ferry NP
Home in Edinburg
4.99 out of 5 average rating, 339 reviewsThe Burrow ~ Our guest reviews say it all!
Home in Bluemont
4.92 out of 5 average rating, 205 reviewsThe Country French Cottage at High Meadows Estate
Home in Edinburg
4.96 out of 5 average rating, 154 reviewsCharming, Parkview Cottage, King bed, 1 mi to I-81
Home in Myersville
4.97 out of 5 average rating, 152 reviewsThe Crooked Cottage: a Cozy, Curated Escape
Home in Sperryville
4.98 out of 5 average rating, 240 reviewsMountaintop Retreat
Home in Greencastle
4.97 out of 5 average rating, 198 reviewsCountry 2-Bed/2-Bath Apartment with Beautiful View
Pet-friendly home rentals with a pool
Guest house in Midland
4.97 out of 5 average rating, 151 reviewsModern Farm Stay
Cottage in Madison
4.96 out of 5 average rating, 336 reviewsTHE PERFECT HIKING & WINERY COUNTRY RETREAT
Guest house in Highland
4.98 out of 5 average rating, 265 reviewsWoodland Retreat
Cottage in Woodstock
4.98 out of 5 average rating, 165 reviewsMuse Vineyards Farmhouse, w Seasonal Pool!
Cabin in Luray
4.91 out of 5 average rating, 125 reviewsEnchanting Log Cabin - River and Mountain Views
Farm stay in Stanardsville
4.91 out of 5 average rating, 672 reviewsAirstream*dogs <3*pool*hottub*mountain*relax*horse
Cabin in Delaplane
5.0 out of 5 average rating, 125 reviewsHerb Cottage-Elegant Cabin on Farm plus Farm Tour!
Home in Harpers Ferry
4.97 out of 5 average rating, 156 reviewsHarpers Ferry Farmhouse, Heated Year Round Pool
Private, pet-friendly home rentals
Holiday home in Front Royal
4.98 out of 5 average rating, 225 reviewsMountaintop Retreat with Wood Fired Hot Tub
Cabin in Paw Paw
4.96 out of 5 average rating, 178 reviewsEasygoing
Guest house in Maurertown
4.97 out of 5 average rating, 375 reviewsGuest Suite at Little Ridge
Cabin in Lost River
4.96 out of 5 average rating, 114 reviewsRustic and stylish mountain getaway
Flat in Woodstock
4.88 out of 5 average rating, 480 reviewsHeart of Town-Pet Friendly
Cabin in Lost River
4.98 out of 5 average rating, 170 reviewsDesign-forward cabin in the woods
Bungalow in Great Cacapon
4.9 out of 5 average rating, 470 reviewsRooster Wrest in the Trees
Cottage in Fort Valley
4.96 out of 5 average rating, 161 reviewsCozy Cottage/Pet Heaven
Quick stats about holiday rentals that are pet-friendly in Winchester
Total rentals
20 properties
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
1.9K reviews
Nightly prices starting at
€ 28 before taxes and fees
Destinations to explore
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