Vacation rentals with a patio in Winchester

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Top-rated patio rentals in Winchester

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Top guest favorite

An outdoor hot tub is shown with a glass of red wine and a single rose placed beside it. A scenic view of rolling fields and trees is visible in the background, with a colorful sunset illuminating the sky.

Cottage in Winchester

4.99 out of 5 average rating, 420 reviews

Uber SXY Private Country Escape! Hot Tub & Views~

Look no further for privacy, intimacy, & fun~ Foxy is your perfect escape, located in the Shenandoah Valley & surrounded by a 1000 private acres but only 10 minutes from downtown Winchester. Offering a uniquely glamorous experience, surrounded by all the beauty of nature. Indulge in luxury & tranquility with amenities including your own private patio with hot tub and million dollar views of the Blue Ridge Mountains. Inside, a full chef's kitchen leading to a sexy, opulent master bedroom suite...

Top guest favorite

A charming cabin is nestled among tall trees, illuminated by soft exterior lighting. The structure features a welcoming porch that extends around the building, while the sky transitions from twilight to dusk, creating a serene atmosphere.

Home in Rio

4.99 out of 5 average rating, 140 reviews

Mountaintop Cabin w/ Outdoor Tub

Come unwind at our mountaintop cabin! Whether it’s the (new cast iron) soaking tub on the back porch, the two hammocks, our giant firepit, or the comfy king bed in the loft, you’ll want to sit, sip, snuggle and tell tall tales as the sun sets and stars shine. Second small bedroom doubles as an office. A gas stove twinkles inside while an antique spiral staircase adds elegance. Fully-equipped kitchen, laundry, and Starlink to provide top-tier connectivity. We’re kid friendly and dog positive too!

Guest favorite

A cozy tiny home is surrounded by lush greenery. Outdoor seating is provided with a small table and chairs, while planters filled with flowers enhance the space. A soaking tub is visible on the patio, adding to the charm of the outdoor area.

Tiny home in Harpers Ferry

4.97 out of 5 average rating, 141 reviews

Enchanting PET FREE W/Amazing ViewHot Tub Overlook

Enjoy majestic views of the Shenandoah River in our tiny home centrally located just 5 mins from AppalachianTrail, 6 mins from the rivers, 12 mins from Old Town Harpers Ferry. Featuring large patio, outdoor dining area, courtyard, firepit, hammock, outdoor 2 person soaking tub. The outdoor space provides private vistas of Shenandoah, moonlit nights, star gazing, "Mind Blowing" outdoor soaking tub or taking in the beautiful scenery while enjoying a relaxing shower in our all cedar shower room.

Superhost

A bright living and dining area features light-coloured furnishings, including a comfortable sofa and a wooden dining table set with dinnerware. A television showcases a scenic view. Warm wooden flooring complements the space, enhanced by natural light from multiple windows.

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

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, 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.

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, 290 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

Cabin in Front Royal

4.94 out of 5 average rating, 236 reviews

The Wizard's Chalet • Cozy nature escape • Hot Tub

Looking for a fun getaway in a relaxing, secluded spot? Come visit The Wizard's Chalet, a cozy & upgraded cabin located in the Shenandoah Valley just one mile from Shenandoah River access and a few miles from restaurants, wineries, basketball & volleyball courts, and more! With a fully stocked kitchen, three cozy bedrooms, high speed WIFI, hot tub, and several beautiful outdoor gathering spaces, this magical cabin is perfect for couples, friends, or the entire family!

Guest favorite

A private patio features two wooden reclining chairs positioned on a patterned rug. A wood-burning hot tub is nestled to one side, surrounded by lush greenery. String lights hang overhead, providing a subtle illumination against the backdrop of a clear blue sky.

Cabin in Star Tannery

4.98 out of 5 average rating, 205 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 modern cabin exterior is shown, featuring a sloped roof and large windows that allow natural light to fill the interior. A spacious deck is visible, furnished with two lounge chairs and a wooden rocking chair, surrounded by vibrant autumn foliage.

Cabin in Winchester

4.95 out of 5 average rating, 107 reviews

Foxtrot Mokki | Secluded Getaway 2 Hours from DC

Welcome to The Foxtrot Mokki—a Nordic-inspired retreat just two hours from DC and Baltimore. Solitude is signature. Nestled on seven secluded acres with rain-fed streams, our cozy cabin is designed for tranquility and connection with nature. Located between Old Town Winchester, VA, and Berkeley Springs, WV, it's the perfect outpost for exploring the Northern Shenandoah Valley—from charming towns to scenic hikes and wineries.

Guest favorite

The exterior of a historic building is showcased, displaying a combination of red and blue painted sections alongside stone walls. Traditional windows with shutters complement the architecture. Flags are positioned by the entrance, and a pathway lined with grass leads to the entrance.

Apartment 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 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

4.92 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

Guest favorite

A table set with checkered linens is surrounded by rustic wooden chairs, situated on a lush green lawn. In the background, a two-story home features a blend of contemporary and rustic design, with prominent windows and a sloped metal roof.

Apartment in Marshall

4.95 out of 5 average rating, 151 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 peaceful 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.