Pet-friendly vacation 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.
Vacation 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, 184 reviewsNewly renovated - Walk to Harpers Ferry NP
Home in Edinburg
4.99 out of 5 average rating, 336 reviewsThe Burrow ~ Our guest reviews say it all!
Home in Woodstock
4.98 out of 5 average rating, 481 reviewsCaretaker Cottage at Burnshire Dam
Home in Bluemont
4.86 out of 5 average rating, 207 reviewsThe Old Schoolhouse at High Meadows Estate
Home in Edinburg
4.96 out of 5 average rating, 152 reviewsCharming, Parkview Cottage, King bed, 1 mi to I-81
Home in Myersville
4.97 out of 5 average rating, 148 reviewsThe Crooked Cottage: a Cozy, Curated Escape
Home in Sperryville
4.97 out of 5 average rating, 239 reviewsMountaintop Retreat
Pet-friendly home rentals with a pool
Guesthouse in Midland
4.97 out of 5 average rating, 151 reviewsModern Farm Stay
Cabin in Hedgesville
4.93 out of 5 average rating, 136 reviewsStylish Retreat with Pool Access and Fire Pit
Cottage in Madison
4.96 out of 5 average rating, 333 reviewsTHE PERFECT HIKING & WINERY COUNTRY RETREAT
Cabin in Luray
4.92 out of 5 average rating, 123 reviewsEnchanting Log Cabin - River and Mountain Views
Farm stay in Stanardsville
4.91 out of 5 average rating, 669 reviewsAirstream*dogFriendly*pool*hottub*mountain*relax
Cottage in Woodstock
4.98 out of 5 average rating, 163 reviewsMuse Vineyards Farmhouse, w Seasonal Pool!
Cabin in Delaplane
5.0 out of 5 average rating, 124 reviewsHerb Cottage-Elegant Cabin on Farm plus Farm Tour!
Cottage in Fredericksburg
4.79 out of 5 average rating, 441 reviews1840's Cottage: 3 miles from I-95/ Near Shopping
Private, pet-friendly home rentals
Guesthouse in New Market
4.99 out of 5 average rating, 182 reviewsStay in a piece of history! Private Entire Cottage
Cabin in Paw Paw
4.96 out of 5 average rating, 178 reviewsEasygoing
Vacation home in Front Royal
4.98 out of 5 average rating, 219 reviewsMountaintop Retreat with Wood Fired Hot Tub
Guest suite in Maurertown
4.85 out of 5 average rating, 187 reviewsStudio along i81: Near Wine, Beer, Hiking & Nature
Bungalow in Great Cacapon
4.9 out of 5 average rating, 467 reviewsRooster Wrest in the Trees
Guesthouse in Myersville
4.93 out of 5 average rating, 191 reviewsSpruce Run Cottage, Farm stay on Catoctin Mountain
Chalet in Martinsburg
5.0 out of 5 average rating, 116 reviewsThe Sage Chalet
Dome in Strasburg
4.94 out of 5 average rating, 377 reviewsHalf-Moon Dome at Our Farm
Quick stats about vacation 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
$30 before taxes and fees
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