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 Bolivar
4.96 out of 5 average rating, 237 reviewsNewly renovated - Walk to Harpers Ferry NP
Home in Harpers Ferry
4.93 out of 5 average rating, 595 reviewsEclectic & Romantic - Walk to Historic Downtown!
Home in High View
4.95 out of 5 average rating, 117 reviewsMtn. View, Creek, 50 Ac, ATV Trails, Near Wash. DC
Home in Chester Gap
4.95 out of 5 average rating, 216 reviewsThe Nest
Home in Bluemont
4.87 out of 5 average rating, 220 reviewsThe Old Schoolhouse at High Meadows Estate
Home in Downtown Frederick
4.98 out of 5 average rating, 103 reviewsHistorically Modern Rowhouse in Downtown
Home in Front Royal
4.95 out of 5 average rating, 108 reviewsCozy house in Shenandoah N.P. City of Front Royal
Home in Springfield
4.98 out of 5 average rating, 126 reviewsRiverside Oasis w/ private estuary & Pup friendly
Pet-friendly home rentals with a pool
Home in Sabillasville
4.93 out of 5 average rating, 107 reviewsStoney Spring Overlook
Tiny home in Fort Valley
4.79 out of 5 average rating, 260 reviewsTiny Cabin Retreat 1 @ Camp Shenandoah Meadows
Cottage in Woodstock
4.98 out of 5 average rating, 183 reviewsMuse Vineyards Farmhouse, w Seasonal Pool!
Guest suite in Bealeton
4.97 out of 5 average rating, 237 reviewsHydrangea House - A Bright and Peaceful Farm Stay
Campervan/RV in New Market
4.98 out of 5 average rating, 104 reviewsPeak season! Glamp before season ends!
Home in Harpers Ferry
4.97 out of 5 average rating, 180 reviewsHarpers Ferry Farmhouse, Heated Year Round Pool
Farm stay in Purcellville
4.97 out of 5 average rating, 156 reviewsThe Hunt Box @ Tally Yo Farm
Cabin in Hedgesville
4.9 out of 5 average rating, 163 reviewsStocked Kitchen w Fireplace and Opt. Pool Access
Private, pet-friendly home rentals
Cottage in Bluemont
4.8 out of 5 average rating, 225 reviewsWine Country Cottage
Cabin in Berkeley Springs
5 out of 5 average rating, 254 reviews+ The Cabin + @ Camp Potomac Peak
Farm stay in Warrenton
4.98 out of 5 average rating, 587 reviewsWinters Retreat Farm Cottage - Entire house
Cabin in Luray
4.94 out of 5 average rating, 267 reviewsCool Cabin w/Firepit & Hot Tub + Fast Wi-Fi
Cabin in Strasburg
4.93 out of 5 average rating, 414 reviewsCedar River Retreat~ River Access~Hot Tub~King Bed
Cabin in New Market
4.92 out of 5 average rating, 158 reviewsThe BlackPearl•Secluded•Hot tub 1.5 hs from DC
Cabin in Luray
4.99 out of 5 average rating, 153 reviewsNew build! Views! Elegant and cozy! - RR
Cabin in Luray
4.81 out of 5 average rating, 262 reviewsPet Friendly | Hot Tub | Fenced Yard | ZEN Garden
Quick stats about holiday rentals that are pet-friendly in Winchester
Total rentals
30 properties
Nightly prices starting at
$51 NZD before taxes and fees
Total number of reviews
2.1K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wi-Fi availability
30 properties include access to Wi-Fi
Destinations to explore
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