Pet-friendly vacation rentals in Winchester

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Top-rated pet-friendly home rentals in Winchester

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Guest favorite

Guest suite in Shepherdstown

4.95 out of 5 average rating, 568 reviews

Historic Scrabble, Shepherdstown

The perfect private guest cottage situated beside a beautiful historic home in the unique community of Scrabble Unincorporated just a half-mile from the Potomac River. Modern, comfortable and tastefully decorated with full amenities and parklike surroundings with an abundance of nature at your doorstep. Close to Shepherdstown / Shepherd Univeristy (12 minutes), Martinsburg (20 minutes), Harpers Ferry (20 minutes) and in the heart of civil war history including the famed Antietam National Park.

Sep 8 – 15

R1,560 ZAR per night

Guest favorite

Home in Winchester

4.97 out of 5 average rating, 167 reviews

Cameron Charmer pristine w/double master suites

Take a step into pure luxury in this newly renovated 1930's charmer in up and coming downtown area of Winchester. Owners have spared no expense to make this the kind of place where guests can come & forget about the rest of the world ! Incredible top of the line centralized dine in kitchen, wide open & inviting living areas, two master suites each with walk in closets & baths up lovely custom pine staircase. Come spoil yourself a bit at the Cameron Charmer, you are sure to enjoy your stay !

Sep 12 – 19

R2,368 ZAR per night

Guest favorite

Farm stay in Round Hill

4.94 out of 5 average rating, 350 reviews

Come and get your goat on!

Nestled at the base of the Blue Ridge and tucked away in the woods, we offer a quiet and peaceful get away while being convenient to tons. Enjoy the peace of 13-acres of woodlands and pasture. A large private deck provides a plenty sun with pasture and woodlands views with some great star watching at night. Miles of walking, the Appalachian trail, fantastic cycling; historic towns and places; wineries, breweries, and distilleries; Potomac and Shenandoah rivers. All just minutes away.

Sep 2 – 9

R2,279 ZAR per night

Guest favorite

Cottage in Winchester

4.9 out of 5 average rating, 100 reviews

Lockley Cottage at Historic Perry Farm

Peace and tranquility await you at a quaint cottage on historic Perry Farm, where the original 19th century farmhouse still stands today. Stroll several acres of land and enjoy pastoral views while you unwind at this peaceful historic property in the hills of northern Shenandoah Valley. This rural retreat is easily accessed from I-81 and located a short 10-minute drive from historic downtown Winchester. Enjoy local wineries, breweries, farm markets, and the renowned Apple Blossom Festival.

Sep 15 – 22

R1,616 ZAR per night

Guest favorite

Home in Edinburg

4.98 out of 5 average rating, 360 reviews

Jay Birds Nest - Pet Friendly

Welcome to Jay Birds nest, located in the historic town of Edinburg, Virginia. Just 1.5 miles from I-81. Fully equipped with all the comforts of home and gorgeous mountain views. Enjoy having the entire house to yourself with sleeping for 6 with 2 queen bedrooms and 1 full bedroom and one full bath. Plenty of parking with room for two cars, one under a car port. Have your morning coffee in the relaxing sunroom or in the outdoor seating area. Just a quick walk away from the Shenandoah River.

Oct 2 – 9

R2,018 ZAR per night

Guest favorite

Apartment in Winchester

4.94 out of 5 average rating, 273 reviews

Downtown 1920's Gas Station

Luxury 1920’s Refurbished Gas Station repurposed into a beautiful apartment. Private off-street parking/EV car charging station, full kitchen, custom shower with rain system, super high speed wifi, smart TV & Blu-Ray. Plenty of light with frosted garaged doors. AC/Heat, Washer/Dryer, Dish Washer, coffee nook, and open living design. Be a part of Old Town Winchester in this unique fun space in walking distance to breweries, neighborhood Pizzoco Pizza parlor and the downtown walking mall.

Nov 4 – 11

R2,597 ZAR per night

Guest favorite

Home in Inwood

4.89 out of 5 average rating, 553 reviews

Arden House, Inwood WV

Ground level studio apartment. No steps. Completely separate entrance from main house. Private entrance and parking. There is an entrance room with a double bed, twin bed and sofa. In a separate living area, there is a queen bed, TV, private bath, desk, table, microwave, convection oven, air fryer, refrigerator Outside there is a large area to use outdoor gas grill, picnic table and fire pit. Dogs allowed and must be kept on a leash when outside. Please NO CATS. The owner is allergic.

Feb 20 – 27

R1,583 ZAR per night

Guest favorite

Apartment in Winchester

4.78 out of 5 average rating, 111 reviews

Yellow Submarine trendy basement apt w/courtyard

Come enjoy the beautiful downtown area of Winchester from this hip Beatles themed walk out basement apt. It is just steps from the Handley Library and walking mall where there is lots to do, shops to explore and yummy food to eat ! You will love the vintage turntable and vinyl. Park & walk to everything cool and inspiring in the city. on site parking space provided. PLEASE Reach out to me thru social media : Michele Bouve Hoffman- if you are looking for shorter than 30 day night stays.

Dec 31 – Jan 7

R1,932 ZAR per night

Guest favorite

Guesthouse in Smithsburg

4.97 out of 5 average rating, 644 reviews

Jewel Vinsota Artist's Guesthouse

Less than a mile from the Appalachian Trail, the dog-friendly Jewel Vinsota guesthouse is the perfect get away to explore nature or your artistic leanings. The house is full of original artwork, hand-crafted details, and books on art and architecture. Wander the grounds and find sculpture, ponds, and trails through the woods. Want to hike the entire 40-mile length of Maryland on the Appalachian Trail? Start and end at the Jewel Vinsota and we can drop you off and pick you up.

Nov 16 – 23

R1,697 ZAR per night

Guest favorite

Cabin in Berkeley Springs

5.0 out of 5 average rating, 205 reviews

+ The Cabin + @ Camp Potomac Peak

The Cabin is the first of three rentals, when coming up the shared driveway at Camp Potomac Peak, and provides everything you need for a weekend in the beautiful mountains of WV. A wrap around deck provides a great hangout space--and includes a private hot tub, outdoor TV, Sonos speaker system, and propane grill. We have two other rentals on the property if you're looking to add more guests--the Cedar + the Lodge! Contact us for a full camp rental (sleeps up to 14).

Jan 13 – 20

R3,620 ZAR per night

Guest favorite

Cabin in Lost River

4.96 out of 5 average rating, 112 reviews

Rustic and stylish mountain getaway

The Little Black Cabin is everything you've been dreaming about for your cozy mountain getaway! Take in sweeping views, curl up by the fireplace, or make s'mores at the fire pit. Whip up a gourmet meal in the small but well-appointed kitchen. Three dining areas offer options for dinner -- or a remote office, thanks to wifi. Sample nearby hiking, yoga, and farmers' market. We're a little rustic (no TV, AC, microwave, laundry or dishwasher) and a lot stylish!

Feb 17 – 24

R1,792 ZAR per night

Guest favorite

Guest suite in Winchester

4.79 out of 5 average rating, 280 reviews

Safe, cozy oasis with private living & bath.

Wonderfully comfortable basement apartment. We are less than a mile from Winchester Medical Center.... ideal for traveling doctors/nurses. Close to other area attractions. You will have your own living room, bathroom and bedroom. Private entrance. Digital lock. You will get instructions prior to check in. You will be in the basement however it has natural light in the bedroom. There may be some noise from upstairs, but it is generally quiet.

Jan 18 – 25

R1,772 ZAR per night