Pet-friendly vacation rentals in Winchester

Find and book unique pet-friendly homes on Airbnb

Quick stats about vacation rentals that are pet-friendly in Winchester

  • Total vacation rentals

    Explore 30 vacation rentals in Winchester

  • Nightly prices starting at

    Winchester vacation rentals start at €26 per night before taxes and fees

  • Verified guest reviews

    Over 2,510 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Winchester vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winchester rentals

  • 4.7 Average rating

    Winchester stays receive an average rating of 4.7 out of 5 from guests

Top-rated pet-friendly home rentals in Winchester

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

1 of 1 pages1 / 1
Top guest favorite
An aerial view reveals a circular yurt, featuring a silver metal roof and a warm wooden exterior. The expansive deck is illuminated by string lights, complementing the private hot tub situated on one side. Surrounded by trees, the outdoor area provides a serene and secluded atmosphere.
Yurt in Front Royal
4.96 out of 5 average rating, 189 reviews

Front Royal Yurt: Hot Tub | Wood Stove | Fire Pit

Escape to the Front Royal Yurt, in Virginia near Shenandoah National Park. A new luxurious retreat in the heart of the breathtaking Blue Ridge Mountains located at 1,300ft! The exceptional Front Royal Yurt blends modern glamping elegance with top-tier comforts, offering an unforgettable getaway. Enjoy a state-of-the-art Modern Yurt, complete with Sunken Hot Tub, 360° Deck with stunning views, Fire Pit, EV Charging Station, Wood-Fired Stove, 77" HDTV, PS5, Pool Table, Books, Board Games & more!

Top guest favorite
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
4.91 out of 5 average rating, 421 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 favorite
A cozy fire pit is surrounded by six white Adirondack chairs, creating an inviting gathering space. Soft lighting is provided by lanterns, while the cottage can be seen in the background, framed by trees under a dusky sky.
Cottage in Boyce
4.95 out of 5 average rating, 155 reviews

Pets? YES! Hot Tub | Fast Wi-Fi | Fire Pit

Moonflower Cottage is a historical farmhouse nestled on two rolling acres in Virginia's wine country. Visit the area's top vineyards, dining, and antique shops. Float down the Shenandoah River. Cap your day sipping cabernet as the sun sets and the cottage blooms like the moonflowers that grow wildly. Bathe in the warm glow of string lights under the grapevine arbor or enjoy a relaxing soak in the spa. Young or old, you are sure to find the vintage that you are looking for at Moonflower Cottage.

Top guest favorite
A well-appointed kitchen features a central island with a marble countertop, surrounded by wooden cabinets and modern appliances. Natural light floods in through large windows, illuminating the dining area with a small table and four chairs. A patterned rug adds warmth to the wooden flooring.
Cottage in Berryville
4.99 out of 5 average rating, 161 reviews

Guest Cottage on Historic Estate & Cattle Farm

Fully restored c.1900 farm house on 190 acre estate, ~1 hr from D.C. Cottage is situated at end of a farm road (past the main house and barns), very private w/ creek and cows right outside. Enjoy walks on the farm, local hikes, breweries & wineries, pick-your-own fruit farms, tubing on the Shenandoah, restaurants, antique shops, and more. 1 queen bdrm and bath on 1st flr, 2nd queen bdrm & loft with twin beds on 2nd flr. wifi, fire pit, small grill. Over 25 only, Max 4 adults. 1 SMALL DOG ONLY.

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
4.98 out of 5 average rating, 208 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
The exterior of the cabin is showcased, featuring large vaulted windows that allow natural light to fill the space. The deck is furnished with a table and chairs, surrounded by a lush yard and trees displaying autumn colors.
Cabin in Gerrardstown
4.98 out of 5 average rating, 208 reviews

The Nest: Modern Cabin Retreat on 5 Wooded Acres

Welcome to The Nest, a light‑filled, chalet‑style cabin tucked into 5 wooded acres. A short drive from Berkeley Springs, Harpers Ferry, and Cacapon State Park, it’s your base for hot springs, hiking, trails, and small‑town restaurants. By day, explore paths, wineries, and historic main streets. By night, come “home” to star‑studded skies, mountain views, and wildlife. With fast Wi‑Fi, a workspace, and a fully stocked kitchen, The Nest is perfect for families, couples, and remote workers.

Guest favorite
An aerial view captures the 1930 stone house set against vibrant autumn foliage and rolling mountains. The home features large windows reflecting the warm colors of nature. A swimming pool is visible in the backyard, surrounded by trees, with ample space for outdoor activities.
Home in Strasburg
4.76 out of 5 average rating, 305 reviews

Cedar Creek Wayside Castle

1930 Stone House 'Mini Castle' on 9 private acres near Strasburg Virginia bordering Cedar Creek Battlefield and Belle Grove Plantation National Park. Home was built by Otis Elevator company in 1930 for their daughter. You have nature trails and fire pit, swimming pool (opened April 15th), deer and wildlife too. Short walk to historic Ceder Creek. Full estate is yours to play and relax. No dogs in pool. Pool is open early April to early October usually. Hot tub is ready year round.

Top guest favorite
A well-lit deck hosts a modern soaking tub, surrounded by forest views. Steps lead down from the deck, which is adorned with warm lighting that highlights the natural wood. The evening sky offers soft hues as the sun sets beyond the trees.
Home in Harpers Ferry
4.97 out of 5 average rating, 129 reviews

Gorgeous cabin on Blue Ridge

Atop the Blue Ridge close to Harper’s Ferry and Virginia wine country this airy retreat overlooks the idyllic Shenandoah. Our two-person soaking tub on a magnificent deck, huge firepit, gorgeous vintage interior, grand piano, and warm pine ceiling and floors, give you the perfect place to get away from city life for a bit. Full kitchen. Two bedrooms plus a big couch that could sleep someone else in a pinch, and a cozy little fireplace top it all off! Just steps to the Appalachian Trail.

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
4.95 out of 5 average rating, 303 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.

Superhost
Cabin in Front Royal
4.99 out of 5 average rating, 454 reviews

Mountaintop Retreat with Wood Fired Hot Tub

Doah House is a private retreat perched on a bluff atop the Blue Ridge, with wide views over the Shenandoah Valley. A calm container for rest and observation, the pace softens, shaped by small rituals: lighting the fire, soaking in the wood-fired tub, making coffee by hand. Weather moves through the trees, changing the light, the air, the sound. Each day feels different. The forest shifts, and you might, too.

Guest favorite
A spacious living area features wooden walls and high ceilings. Large windows allow natural light to fill the space. A blue couch and matching accent chair are positioned around a black and white rug. A dining table with chairs is visible, alongside a console with a TV.
Cabin in Strasburg
4.92 out of 5 average rating, 567 reviews

Cedar River Retreat~ River Access~Hot Tub~King Bed

Gorgeous log cabin nestled in the forest with lovely river access within the community. Soak in serenity, visit nearby wineries, go antiquing and of course canoe, kayak, or float down the river, or simply sit on the bank and listen to the water rush by. Walk through our wooded lot and you will see deer, squirrels, and Willy, our resident grandaddy groundhog (he loves apples if you want to bring him a treat.)

Top guest favorite
Cabin in Front Royal
4.97 out of 5 average rating, 127 reviews

The Cozy Bear Cabin | Hot Tub, Fenced Yard, Games

Tucked away in the woods of Front Royal, Cozy Bear Cabin is a warm retreat with space to gather and unwind. Enjoy 3 king bedrooms, 3 full baths, a propane-fireplace living room, a stocked kitchen with island, plus a game room and movie theater. Outside, grill and dine on the decks, soak in the hot tub under string lights, and enjoy a fenced yard—minutes from hikes, caverns, Skyline Drive, and wineries.

Popular amenities for Winchester pet-friendly home rentals

When is the best time to visit Winchester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price€119€119€121€121€122€126€106€77€74€82€91€91
Avg. temp1°C3°C7°C13°C18°C23°C25°C24°C20°C14°C8°C3°C