Pet-friendly vacation rentals in Winchester
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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
Nov. 26 – Dec. 3
Home in Bolivar
4.96 out of 5 average rating, 184 reviewsNewly renovated - Walk to Harpers Ferry NP
Oct. 22 – 29
Home in Bluemont
4.93 out of 5 average rating, 203 reviewsThe Country French Cottage at High Meadows Estate
Feb. 1 – 8
Home in Edinburg
4.99 out of 5 average rating, 336 reviewsThe Burrow ~ Our guest reviews say it all!
Apr. 15 – 22
Home in Myersville
4.97 out of 5 average rating, 148 reviewsThe Crooked Cottage: a Cozy, Curated Escape
Oct. 8 – 15
Home in Edinburg
4.96 out of 5 average rating, 149 reviewsCharming, Parkview Cottage, King bed, 1 mi to I-81
Sep. 11 – 18
Home in Harpers Ferry
4.94 out of 5 average rating, 521 reviewsEclectic & Romantic - Walk to Historic Downtown!
Mar. 31 – Apr. 7
Home in Sperryville
4.97 out of 5 average rating, 239 reviewsMountaintop Retreat
Apr. 3 – 10
Pet-friendly home rentals with a pool
Cabin in Hedgesville
4.93 out of 5 average rating, 134 reviewsStylish Retreat with Pool Access and Fire Pit
Jan. 26 – Feb. 2
Guesthouse in Midland
4.97 out of 5 average rating, 151 reviewsModern Farm Stay
Oct. 14 – 21
Cabin in Luray
4.92 out of 5 average rating, 123 reviewsEnchanting Log Cabin - River and Mountain Views
Jan. 14 – 21
Cottage in Madison
4.96 out of 5 average rating, 332 reviewsTHE PERFECT HIKING & WINERY COUNTRY RETREAT
Sep. 27 – Oct. 4
Cottage in Woodstock
4.98 out of 5 average rating, 163 reviewsMuse Vineyards Farmhouse, w Seasonal Pool!
Oct. 19 – 26
Farm stay in Stanardsville
4.91 out of 5 average rating, 669 reviewsAirstream*dogFriendly*pool*hottub*mountain*relax
Sep. 13 – 20
Guest suite in Myersville
4.93 out of 5 average rating, 279 reviewsHarmony Lodge nestled in wooded tranquility!
Dec. 6 – 13
Cabin in Delaplane
5.0 out of 5 average rating, 124 reviewsHerb Cottage-Elegant Cabin on Farm plus Farm Tour!
Nov. 10 – 17
Private, pet-friendly home rentals
Farm stay in Warrenton
4.98 out of 5 average rating, 525 reviewsWinters Retreat Farm Cottage - Entire house
Sep. 30 – Oct. 7
Bungalow in Great Cacapon
4.9 out of 5 average rating, 466 reviewsRooster Wrest in the Trees
Oct. 29 – Nov. 5
Guesthouse in Maurertown
4.97 out of 5 average rating, 375 reviewsGuest Suite at Little Ridge
Sep. 24 – Oct. 1
Farm stay in Round Hill
4.94 out of 5 average rating, 348 reviewsCome and get your goat on!
Jul. 15 – 22
Guesthouse in Myersville
4.93 out of 5 average rating, 191 reviewsSpruce Run Cottage, Farm stay on Catoctin Mountain
Jul. 15 – 22
Vacation home in Front Royal
4.98 out of 5 average rating, 219 reviewsMountaintop Retreat with Wood Fired Hot Tub
Jul. 15 – 22
Guest suite in Maurertown
4.85 out of 5 average rating, 187 reviewsStudio along i81: Near Wine, Beer, Hiking & Nature
Jun. 17 – 24
Guesthouse in Syria
4.95 out of 5 average rating, 331 reviewsLittle House on Strother Run
Aug. 18 – 25
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
$41 CAD before taxes and fees
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