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.

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Guest favorite

A well-maintained exterior showcases a brick building with a white double door entrance. Surrounding greenery includes manicured lawns and bushes, enhancing the natural setting. The entrance is easily accessible, providing a welcoming approach to the ground-level unit.

Home in Inwood

4.88 out of 5 average rating, 645 reviews

Arden House, Inwood WV

Ground level two room unit. No steps. Separate entrance from main house. Private entrance and parking. There is an entrance room with a double bed, twin bed, sofa and full refrig.. In a separate living area, there is a queen bed, TV, bathroom, desk, table, microwave, convection oven, air fryer, gas fireplace. No oven. 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.

Superhost

A contemporary building with a mix of stone and modern gray walls is showcased, featuring large glass windows and wooden accents. A bright yellow door provides a pop of color at the entrance. The surrounding area includes wooden railings and landscaped greenery.

Apartment in Winchester

4.9 out of 5 average rating, 350 reviews

Downtown 1920's Gas Station with Hot Tub

Luxury 1920’s Refurbished Gas Station and hot tub repurposed into a beautiful apartment. Private parking/EV charging station, private hot tub, full kitchen, custom rain shower, high speed wifi, and smart TV. There is plenty of light with frosted garaged doors, all modern appliances, coffee nook, and an open living design. Be a part of Old Town Winchester in this unique getaway, walking distance to shops, downtown eateries and our neighborhood Pizzoco Pizza Parlor one block away. Pets welcome!

Top guest favorite

A cozy living space features a wooden ceiling and light-colored walls. A small electric fireplace is placed beneath a wall-mounted television. A coffee table sits centrally, surrounded by two comfortable chairs and a couch, with a front door visible to the side.

Cabin in High View

4.97 out of 5 average rating, 141 reviews

Mary's Cabin

Nestled on 2 acres in the woods of West Virginia, kick back and relax in this quiet, chic cabin. Soak in the oversized copper tub, read on the porch swing, or cuddle by the electric fireplace. All the amenities of home, but away from the hustle and bustle of daily life. Only 25 minutes to quaint Old Town Winchester, where there are unique shops, breweries, restaurants and history! The cabin is located 20 minutes from a variety of scenic hiking trails that provide opportunities for adventure.

Top guest favorite

A welcoming single-story house is shown, featuring a front yard with neatly arranged shrubs and flowers. A pathway leads to the entrance, which is flanked by potted plants. A carport is visible on one side, providing covered parking.

Home in Edinburg

4.97 out of 5 average rating, 511 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.

Top guest favorite

A spacious living area features vaulted ceilings with large windows allowing natural light to fill the room. A comfortable sofa faces a central coffee table, with a dining area containing a round table and chairs nearby. Shelving units display books and decorative items, enhancing the inviting space.

Cabin in Gerrardstown

4.99 out of 5 average rating, 152 reviews

The Nest: Cozy Chalet w/Wi-Fi, Deck & Grill

The Nest is a chalet-style cabin tucked into the tree-lined mountains of Berkeley County, WV. It offers adventure, a quiet retreat & good family fun. With 5-acres in the countryside, you'll enjoy star studded skies on clear nights & wake up to birds singing & deer wandering, with mountain views through vaulted windows. The Nest is near Martinsburg, Berkeley Springs, Harpers Ferry, Shepherdstown, Charles Town & Cacapon State Park, among other go-to destinations on the Eastern Panhandle.

Top guest favorite

The exterior of a two-story house is surrounded by trees, with warm lights framing the balconies. Large glass windows provide visibility into the interior. A deck with a railing is seen above, and decorative elements are positioned outside the entrance.

Guest suite in Smithsburg

4.98 out of 5 average rating, 258 reviews

Creekside Retreat at the Jewel Vinsota

Relax in a quiet, curated, pet-friendly art exhibit. Live with paintings & sculptures that are for sale. This garden apartment is tucked into a hillside above a creek, along the Jewel Vinsota Sculpture Trail. Your host/gallery curators live upstairs. The “Artist’s Guesthouse” is next door. The private entrance is down a stone-stepped path. Perfect for 2 w/ the queen bed but room for 3 w/ the living room futon. Fully equipped kitchen. Private charcoal grill and fire pit next to the creek.

Guest favorite

A spacious grassy area is framed by a charming yellow house nestled among trees, where several goats graze peacefully. A car is parked nearby, and outdoor seating is arranged on a wooden platform in the background, creating a welcoming rural scene.

Farm stay in Round Hill Village

4.93 out of 5 average rating, 411 reviews

The Goat Loft - A Private, Peaceful Getaway!

Private Blue Ridge Retreat – Nature, Hiking, and Relaxation Escape to 13 acres of peaceful woodlands and pasture at the base of the Blue Ridge Mountains. Enjoy the goats from the private deck, perfect for stargazing at night! Nearby, hiking on the Appalachian Trail, cycle scenic routes, or explore historic towns, wineries, and breweries. The Potomac and Shenandoah Rivers offer even more outdoor adventures. A perfect mix of tranquility and adventure, but just minutes from everything!

Guest favorite

A wooden yurt stands beautifully at dusk, illuminated by soft string lights. A wraparound deck features a fire pit surrounded by outdoor seating, with the tranquil mountains providing a scenic backdrop under a colorful sunset sky.

Yurt in Front Royal

4.97 out of 5 average rating, 139 reviews

Skyline Yurt: Hot Tub~Wood Stove~WiFi~EVcharger

Skyline Yurt is a one-of-a-kind luxury getaway nestled in the tranquil serenity of the mountains. Here, you won't find any compromises with respect to the top-notch cabin-like structure, modern amenities, a hot tub, wood-burning stove, archery, EV charger, spacious elevated deck, pool table, board games, and so much more! This magnificent pet-friendly Skyline Cabin / Yurt is surrounded by the captivating scenery of Virginia's Blue Ridge Mountains at an elevation of over 1,100 ft!

Top guest favorite

The exterior view of the cottage features a walkway leading to a white door, flanked by climbing roses and hanging flower pots. A small outdoor table and chairs are set on the gravel, inviting guests to enjoy the pleasant surroundings.

Guesthouse in New Market

4.98 out of 5 average rating, 344 reviews

Stay in a piece of history! Private Entire Cottage

Built in 1797, this cottage sits next to the historic William Rupp House, and is #17 on the self-guided walking tour! Although you are staying in a piece of history, you still get the privacy you need to comfortably explore all Shenandoah Valley has to offer. 19.6 miles away from JMU, 5.2 miles away from Endless Caverns, right off Interstate 81, and within walking distance of local stores, coffee shops, and restaurants... buckle in for a load of fun with this convenient location.

Guest favorite

The inviting living room features a cozy dark blue sofa adorned with various colorful pillows. A red coffee table sits in front, complemented by a soft area rug and warm natural light flooding through the large windows. A beige armchair and decorative accents add to the ambience.

Home in Winchester

4.95 out of 5 average rating, 188 reviews

Indigo Blue modern open vibe on tree lined street

Come stay in this lovely spacious downtown home located on a beautiful tree lined street. Enjoy its open mid century modern style and relaxing outdoor areas! This 3BR 2BA home w/ sunroom w/ gas fireplace & rear fully fenced courtyard is the perfect place get away to & explore downtown Winchester. Walking distance to everything. Park & walk & enjoy nearby John Handley HS /walking mall /shopping/live music /art galleries/ walk to the iconic Handley Library, You will LOVE it!

Guest favorite

A stone fireplace is the focal point of the cozy main room, surrounded by wood flooring and natural light. Open shelving displays decorative items. A small kitchen features wood cabinetry, while a dining area is visible in the background, enhancing the inviting layout.

Cabin in Lost River

4.97 out of 5 average rating, 173 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!

Guest favorite

A welcoming living area features a patterned couch adorned with soft pillows, positioned under warm lighting. A small coffee table rests in front, and a TV stands on a wooden console. Minimalist decor includes floral artwork on the wall, complemented by wooden accents.

Guest suite in Winchester

4.81 out of 5 average rating, 339 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.