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.

0 of 0 items showing

1 of 3 pages

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

4.87 out of 5 average rating, 661 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, 360 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, 149 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, 537 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

4.98 out of 5 average rating, 158 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

Place to stay in Bentonville

4.99 out of 5 average rating, 470 reviews

John Pope Cabin Browntown Va. We now have Starlink

Our cabin, located in the foothills of the Appalachian Mountains is uniquely positioned overlooking a large open field where hawks hunt and bears leisurely stroll. Our neighbors have horses that peer over the fence (nosy) pet them but don’t feed them, please. Our cabin was built in 1865 by a Confederate soldier returning from the Civil War. Eleven children were born and raised in John Pope Cabin. Our cabin is rustic. A large front porch with swing is waiting for you. @walnuthillcabin

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, 191 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 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, 345 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.

Guest favorite

A modern cabin is set amongst lush greenery, featuring a dark exterior and a welcoming front porch. Surrounding landscaping includes a variety of shrubs and trees, creating a peaceful atmosphere. The driveway leads to the entrance, providing easy access to the secluded retreat.

Cabin in Star Tannery

4.98 out of 5 average rating, 187 reviews

Cabin With Wood Burning Hot Tub

Escape to our modern cabin on 12 private acres. Unwind in the wood-burning hot tub, embracing the surroundings and stars at night. With a contemporary design and natural light, this retreat blends with nature. Explore private trails throughout the property, enjoying nature and the fresh air. Inside, find comfort in the fully equipped kitchen and cozy living area. Perfect for a peaceful getaway, our secluded home provides privacy and relaxation.

Guest favorite

A welcoming outdoor patio features a white rocking chair positioned beside a small white table. A potted plant adds greenery against the light-colored brick wall. Natural light illuminates the area, enhancing the charming appeal of this historic setting.

Apartment in Winchester

4.91 out of 5 average rating, 111 reviews

Newly repurposed Historic Home in Winchester VA!

The historic “Homespun” is located on the border between Frederick County and the city of Winchester. Originally built in the mid 1790’s the Homespun is significant in local architecture as an example of a dogtrot-plan structure, a rare building form of this period. The property is listed on the National register of Historic Places and Virginia Landmark Registry.

Guest favorite

A cozy sleeping area features a spacious bed layered with white and grey bedding, accented by a red throw. Soft lighting from bedside lamps illuminates the natural wood walls, while shelves display decorative items. A flat-screen TV is mounted above the bed.

Guest suite in Stephens City

4.95 out of 5 average rating, 100 reviews

Cozy Cabin

Take it easy at this unique and tranquil getaway. About an hour from D. C. , Luray Caverns, and very close to Historic Downtown Winchester. Take your canoe on the small lake behind the property to joyride or even fish! Shop and get a small town feel in this cozy cabin. If you would like to bring your pet there is a pet fee of $40 that will be added! Thank you

Top guest favorite

A cozy porch area features natural wood beams and a spacious of wicker seating arrangement. A rug with geometric patterns is laid on the wooden floor. A small round table and decorative items add charm, with snow visible outside the windows.

Apartment in Marshall

4.94 out of 5 average rating, 143 reviews

The Lodge at Turkey Creek

Your low tech getaway awaits in the VA Piedmont wine & hunt country! Nestled in the woods at the end of a half mile private drive you will find quiet & solitude. Your tranquil sanctuary includes a charming lower level apartment and patio. Located in the midst of expansive horse farms, charming towns, idyllic scenery, mountains and wineries.