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.

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Guest favourite

Home in Inwood

4.87 out of 5 average rating, 674 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

Flat in Winchester

4.9 out of 5 average rating, 364 reviews

Old Town 1920s Gas Station with Hot Tub

1920s Refurbished Gas Station with hot tub repurposed into a beautiful luxury apartment. Private parking/EV charging, 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, laundry and coffee nook in 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!

Guest favourite

Home in Middletown

4.92 out of 5 average rating, 118 reviews

Cozy Reliance Retreat with Beautiful Views

Welcome to the Reliance Retreat in the heart of the Shenandoah Valley! Our luxurious space is inviting and tranquil. Whether you're just passing through or need some peace and quiet away from the city, this cozy house has an amazing mountain view we know you'll enjoy. The house sleeps four and includes all the amenities you'll need in every area of the home. We hope you'll grab a book, your favorite snacks and find yourself a cozy spot whether it's inside, on the patio, or out by the fire pit

Top guest favourite

Cabin in High View

4.97 out of 5 average rating, 156 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 favourite

Cabin in Gerrardstown

4.98 out of 5 average rating, 167 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.

Guest favourite

Home in Winchester

4.93 out of 5 average rating, 159 reviews

Historic District Charm On Cameron Street

Charming home located in the historic district of Winchester. A short walk to the walking mall,restaurants, shopping, farmer's markets,breweries and more. Convenient to Shenandoah University, Winchester Medical Center, many museums including the Museum of the Shenandoah Valley, George Washington Hotel, Skyline Drive, 81 and more. Big deck and a half court basketball in the back yard. We have added a work/office area with a desk and chair ideal for working or schooling from home.

Guest favourite

Home in Winchester

4.95 out of 5 average rating, 195 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 & relaxing outdoor area! This 3BR 2BA home w/sunroom w/ gas fireplace & rear fully fenced courtyard perfect place to get away to & explore downtown Winchester. Walking distance to everything. Walking Mall/ Shopping /Live Music /Art/ John Handley Library/Discovery Museum. Need shorter stay? Contact info for : Michele Bouve Hoffman via google.

Guest favourite

Guest suite in Winchester

4.81 out of 5 average rating, 350 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 favourite

Flat in Winchester

4.91 out of 5 average rating, 113 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 favourite

Guest suite in Stephens City

4.92 out of 5 average rating, 108 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 favourite

Flat in Winchester

4.98 out of 5 average rating, 105 reviews

Cozy Apartment located on our 5-acre property

Airbnb in Winchester, pet friendly! We love long term stays & get plenty of travel nurses & travel professionals who never want to leave :) We live on 5 acres nestled in our own little piece of heaven, located in Shenandoah Valley. We raise chickens and bees. This is a beautiful country getaway perfect for relaxing with a nice drive to old town Winchester.

Guest favourite

Cabin in Winchester

4.96 out of 5 average rating, 112 reviews

Spectacular Views w/ Hot tub, Fire Pit, King Beds

Welcome to your serene A-frame retreat in Winchester, VA! 🏡✨ This stylish 3BR, 2BA cabin is perfect for relaxation or adventure. Inside, enjoy a beautiful blend of Japanese minimalism 🇯🇵, Scandinavian coziness ❄️, and mid-century charm 🛋️ with clean lines, neutral tones, and natural materials creating a peaceful, modern escape. 🌿