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
6–13 Dec
Home in Woodstock
4.98 out of 5 average rating, 480 reviewsCaretaker Cottage at Burnshire Dam
20–27 Oct
Home in Bolivar
4.96 out of 5 average rating, 184 reviewsNewly renovated - Walk to Harpers Ferry NP
28 Jul – 4 Aug
Home in Edinburg
4.99 out of 5 average rating, 336 reviewsThe Burrow ~ Our guest reviews say it all!
21–28 Nov
Home in Bluemont
4.92 out of 5 average rating, 204 reviewsThe Country French Cottage at High Meadows Estate
13–20 Jan
Home in Edinburg
4.96 out of 5 average rating, 151 reviewsCharming, Parkview Cottage, King bed, 1 mi to I-81
11–18 Sep
Home in Myersville
4.97 out of 5 average rating, 148 reviewsThe Crooked Cottage: a Cozy, Curated Escape
4–11 Sep
Home in Sperryville
4.97 out of 5 average rating, 239 reviewsMountaintop Retreat
30 Jan – 6 Feb
Pet-friendly home rentals with a pool
Cabin in Hedgesville
4.93 out of 5 average rating, 135 reviewsStylish Retreat with Pool Access and Fire Pit
17–24 Feb
Guest house in Midland
4.97 out of 5 average rating, 151 reviewsModern Farm Stay
14–21 Oct
Guest house in Highland
4.98 out of 5 average rating, 264 reviewsWoodland Retreat
18–25 Sep
Cottage in Madison
4.96 out of 5 average rating, 332 reviewsTHE PERFECT HIKING & WINERY COUNTRY RETREAT
27 Sep – 4 Oct
Cabin in Luray
4.92 out of 5 average rating, 123 reviewsEnchanting Log Cabin - River and Mountain Views
12–19 Mar
Farm stay in Stanardsville
4.91 out of 5 average rating, 669 reviewsAirstream*dogFriendly*pool*hottub*mountain*relax
21–28 Apr
Cottage in Woodstock
4.98 out of 5 average rating, 163 reviewsMuse Vineyards Farmhouse, w Seasonal Pool!
19–26 Oct
Cottage in Fredericksburg
4.79 out of 5 average rating, 441 reviews1840's Cottage: 3 miles from I-95/ Near Shopping
16–23 Mar
Private, pet-friendly home rentals
Farm stay in Warrenton
4.98 out of 5 average rating, 525 reviewsWinters Retreat Farm Cottage - Entire house
30 Sep – 7 Oct
Bungalow in Great Cacapon
4.9 out of 5 average rating, 467 reviewsRooster Wrest in the Trees
29 Oct – 5 Nov
Guest house in Myersville
4.93 out of 5 average rating, 191 reviewsSpruce Run Cottage, Farm stay on Catoctin Mountain
9–16 Jul
Holiday home in Front Royal
4.98 out of 5 average rating, 219 reviewsMountaintop Retreat with Wood Fired Hot Tub
1–8 Feb
Chalet in Martinsburg
5.0 out of 5 average rating, 116 reviewsThe Sage Chalet
16–23 Dec
Guest suite in Maurertown
4.85 out of 5 average rating, 187 reviewsStudio along i81: Near Wine, Beer, Hiking & Nature
17–24 Jun
Cabin in Lost River
4.98 out of 5 average rating, 168 reviewsDesign-forward cabin in the woods
2–9 Jul
Guest house in Syria
4.95 out of 5 average rating, 332 reviewsLittle House on Strother Run
12–19 Aug
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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