Holiday rentals with a patio in Winchester

5 out of 5 average rating, 116 reviews

The cabin is nestled among tall trees, supported by stilts. Its architecture features a combination of dark siding and wooden beams, with a spacious deck visible, furnished with outdoor seating. Natural greenery surrounds the structure, creating a peaceful atmosphere.

Cabin in Woodstock

The Bird's Nest - Cabin by the River

Located on one of the Seven Bends of the Shenandoah River, the Bird’s Nest is a brand new, custom built 800 square foot cabin featuring an open loft with king bed and skylights, steam shower, heated bathroom floor, and gas fireplace. Exterior amenities include a hot tub, gas grill, gas fire pit table, fire pit by the river, and private river access in a peaceful, wooded setting. Kayaks/tubes are available to use to float down the river with the unique ability to park/exit on the hosts’ property.

Tiny home in Harpers Ferry

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.

4.96 out of 5 average rating, 156 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. Quiet away from the train in old town Large patio, courtyard, firepit, hammock, outdoor 2 person soaking tub. The outdoor space provides private vistas of Shenandoah, moonlit nights, star gazing, "Mind Blowing" soaking tub or taking in the beautiful scenery while enjoying a relaxing shower in our all cedar shower room.

4.99 out of 5 average rating, 433 reviews

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

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...

4.91 out of 5 average rating, 127 reviews

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

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

4.97 out of 5 average rating, 178 reviews

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

The Nest: Cozy Chalet - Wi-Fi, Deck and 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 mountainside, 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.

5 out of 5 average rating, 130 reviews

The exterior of a renovated log cabin is showcased, featuring traditional log and chink construction. A substantial stone chimney rises alongside the cabin. A spacious porch is present, equipped with a couple of white chairs, surrounded by natural greenery and autumnal foliage.

Cabin in Springfield

1832 Historic Washington Bottom Farm Log Cabin

Welcome to our renovated 1832 Log Cabin on the grounds of the George William Washington and Sarah Wright Washington 19th century plantation. The cabin was the first structure built. Then came barns and slaves’ quarters (no longer standing). The dairy barn is now a woodworking shop and the bank barn was recently restored. The main house, built in 1835, is Greek Revival style. Today, our 300+acre is Certified Organic. We border the South Branch of the Potomac River. It’s ALMOST HEAVEN !

Cabin in Berkeley Springs

A modern two-story home is nestled among trees, featuring a large deck with outdoor seating and expansive glass windows. The exterior is a combination of dark wood siding and metal accents, while a gravel area is visible nearby, enhancing the natural setting.

4.99 out of 5 average rating, 140 reviews

Monte Vista~Golf~Views~PS5~Sport Court~EV Charger

IG @montevistawv Luxury Getaway Professionally Designed for STR 🏔️Massive Panoramic 3 State View 🏌️‍♂️Golf Ball Driving Range 🏀 Pickleball, Basketball, Volleyball & Tennis 🎮 PlayStation 5 Mini Disc ♨️ 6-Person Hot Tub 🔊Sonos Sound Throughout 🔋Level 2 EV Charger 🥾 Hiking Trail on site 🌳 33 private acres, no quiet hours 🔥 Massive Firepit + Grill & Pizza Oven 🛋️ Cozy Gas Fireplace 🌐 Fast WiFi & Three 65" Smart Tvs 🛏️ 3 King Beds & Twin Bunk Bed 💼 Dedicated Work Area

4.95 out of 5 average rating, 253 reviews

A classic A-frame cabin is surrounded by trees, featuring a spacious deck with comfortable lounge seating. Soft lighting accentuates the inviting outdoor space, while large glass doors provide a glimpse into the cozy interior. The modern roof complements the rustic wooden facade.

Cabin in Front Royal

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!

4.96 out of 5 average rating, 224 reviews

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

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.

4.94 out of 5 average rating, 125 reviews

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

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.

4.88 out of 5 average rating, 154 reviews

The exterior of a vintage red schoolhouse is shown, featuring white picket fencing and a gravel driveway. A flagpole stands proudly with the American flag, while the surrounding landscape includes gently rolling hills. Soft lighting from the house illuminates the entryway, enhancing the inviting appearance.

Home in Cross Junction

Little Red Schoolhouse in Cross Junction

Step into our charming red schoolhouse—your cozy, vintage-inspired 1BR retreat! Enjoy a unique stay with modern comforts, nostalgic décor, and sun-filled spaces. Perfect for romantic getaways or peaceful escapes. High ceilings, natural light, and warm wood floors set the scene. Just minutes from scenic hikes, wineries, and local attractions. Book your unforgettable Airbnb experience now in this one-of-a-kind historic stay!

Guest suite in Stephens City

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.

4.9 out of 5 average rating, 119 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 $60 will be added. Please list your pet when booking. Thank you

Popular amenities for rentals with patio in Winchester

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Flat rentals with a patio

4.89 out of 5 average rating, 118 reviews

A serene riverfront view is presented, featuring lush greenery along the banks of a calm river. Tall trees and gentle grasses frame the water, reflecting the surrounding landscape. A fire pit is partially visible on the right, positioned on a grassy area near the water's edge.

Flat in Elkton

Rustic River Retreat- 2 Bedroom Riverfront Lodging

4.98 out of 5 average rating, 114 reviews

A cozy living area is equipped with a vibrant yellow armchair and a light gray sectional sofa. A large screen TV is mounted on the wall, and natural light enters through a window adorned with white curtains. A round wooden coffee table sits on a patterned area rug.

Flat in Culpeper

Red Fox Retreat

4.92 out of 5 average rating, 137 reviews

The living room features two dark blue sofas with decorative throw pillows, arranged around a circular coffee table on a light area rug. A ceiling fan and minimalist shelving contribute to the room's relaxed ambiance. Natural light enters through a nearby window.

Flat in Harrisonburg

5 mins to downtown shops + JMU | Smart TV | deck

4.93 out of 5 average rating, 123 reviews

A spacious living area features a comfortable gray sectional sofa with patterned throw pillows. Two accent chairs complement the seating arrangement, while a decorative coffee table sits atop a textured area rug. Large windows allow natural light to fill the room, enhancing the neutral color scheme.

Flat in Frederick

Charming Historic Downtown Apartment…The Fox’s Den

4.98 out of 5 average rating, 132 reviews

A covered patio area is presented with a picnic table and a decorative rug. Lush flower beds filled with vibrant blooms line the space, adding color and charm. A small wooden chair enhances the inviting outdoor setting.

Flat in Hagerstown

Private, relaxing, scenic 2 bdrm unit, Sleeps 1-5

4.85 out of 5 average rating, 20 reviews

A cozy bedroom features a spacious bed topped with neutral-toned bedding. Two bedside lamps provide soft illumination, while natural light enters through two windows adorned with woven shades. A brick accent wall adds warmth, complemented by wooden flooring and a decorative rug.

Flat in Winchester

Two Bdrm. Flat w/ Patio Terrace

4.99 out of 5 average rating, 136 reviews

A comforting sleeping area features a spacious bed topped with a patterned quilt. A soft cloud-shaped pillow adds a touch of whimsy. Light flows through a window adorned with soft shades, with a small round table nearby, enhancing the inviting ambiance of the room.

Flat in Front Royal

Cozy 1BR for Couples & Solo Travel~No Cleaning Fee

Flat in Downtown Frederick

The top left image displays the Carroll Creek Promenade, featuring a serene waterway lined with colorful banners and greenery. The top right image showcases a bright bedroom, furnished with a spacious bed and bedside tables. The bottom left image presents a cozy living area with two chairs and decorative pillows. The bottom right image captures a kitchen equipped with wooden cabinetry, modern appliances, and a dining area.

4.96 out of 5 average rating, 182 reviews

King Bed Apt./Carroll Creek Promenade

House rentals with a patio

4.97 out of 5 average rating, 307 reviews

A living area features a comfortable beige sofa and an adjacent dining table with two chairs. A small desk with a chair and laptop is positioned nearby. Sunlight enters through a window adorned with white blinds, illuminating the relaxed atmosphere.

Home in Bolivar

Day Street - Walk to Harpers Ferry NP

4.94 out of 5 average rating, 120 reviews

Aerial view of a picturesque home surrounded by vibrant autumn foliage. Rolling hills are visible in the background, while the golden and orange leaves create a warm tapestry across the landscape, complemented by a tranquil sunset sky.

Home in Rileyville

ShenandoahEscape~HotTub~OutdoorCinema~DogFriendly

4.72 out of 5 average rating, 116 reviews

A tree-lined driveway leads to a charming home, partially obscured by lush greenery. Sunlight filters through the leaves, casting gentle shadows on the well-maintained lawn. The sky is bright with fluffy clouds, contributing to a serene, inviting atmosphere.

Home in Hagerstown

Private Country Club Home

4.92 out of 5 average rating, 125 reviews

A historical stone Dutch Colonial home features a welcoming front porch with seating. Lush greenery and trimmed hedges surround the entrance, while a smooth driveway guides visitors. The pitched roof and brick chimney enhance the traditional architectural style of the residence.

Home in Shepherdstown

The Dorothy Historical home in Shepherdstown, WV

4.93 out of 5 average rating, 107 reviews

An A-Frame home is surrounded by trees, featuring a stone patio with four black lounge chairs arranged around a circular fire pit. The exterior is fitted with large windows, allowing for ample natural light.

Home in Gerrardstown

A-Frame Mountain Retreat

4.93 out of 5 average rating, 164 reviews

A spacious screened porch features a comfortable sectional sofa arranged around a wooden coffee table. Natural light filters through the screens, providing views of the surrounding trees and expansive yard.

Home in Luray

Cabin with Private Waterfront, On River, Fast Wifi

4.9 out of 5 average rating, 101 reviews

An indoor saltwater pool area features a large, tranquil pool surrounded by multiple windows allowing natural light. Lounge chairs line one side, with red and white striped towels neatly arranged. The ceiling is accented with skylights, enhancing the spacious feel.

Home in Luray

Indoor Heated Pool~WiFi~ Arcade~Fire Pit~Views

4.9 out of 5 average rating, 155 reviews

A serene view of a river winding through a lush forest. A charming two-story building with a red roof is positioned near the water's edge, surrounded by greenery. The landscape features rocky banks and a variety of trees, creating a peaceful rural setting.

Home in Berkeley Springs

Peaceful Waterfall House is waiting for you.

Apartment rentals with a patio

4.96 out of 5 average rating, 123 reviews

A spacious living area features a pool table centered on a patterned rug. Comfortable seating options surround the space, with light-colored walls complementing the decorative elements. A tall plant adds a touch of greenery, while various artwork adorns the walls, contributing to a welcoming environment.

Apartment in Frederick

2 Queen & 1 Twin Bed / Mountain & Museum Fun

4.94 out of 5 average rating, 122 reviews

A cozy seating area features a patterned sofa and a coffee table, positioned in front of a queen-size bed with red and blue accents. Exposed stone walls create a rustic charm, while soft lighting enhances the inviting ambiance.

Apartment in Warrenton

Historic Two Bedroom in Old Town Warrenton

4.95 out of 5 average rating, 155 reviews

Apartment in Frederick

Quiet Stay + Huge Apt + Hot Tub + Dogs, Walkable

Apartment in Mount Jackson

The living area features a stone fireplace, complemented by a stack of firewood beside it. A large leather sofa and a sleek black armchair surround a round table, while expansive windows provide natural light and views of the outdoors.

4.8 out of 5 average rating, 121 reviews

The Room with the Views!

4.94 out of 5 average rating, 229 reviews

A cozy living area features a spacious sectional sofa adorned with patterned cushions. A round table is accompanied by wooden chairs, while a minimalist coffee table sits on a plush area rug. Natural light enters through multiple windows, highlighting the room's inviting design.

Apartment in Leesburg

Downtown 1 BR Condo Steps to Everything

4.99 out of 5 average rating, 89 reviews

The living room is characterized by exposed brick walls and large windows allowing natural light. Comfortable black leather sofas are arranged around a central table, while a cozy bean bag chair adds to the seating options. Decorative elements include a framed artwork and vibrant curtains.

Apartment in Winchester

Historic District Downtown Winchester

4.9 out of 5 average rating, 51 reviews

A combined living and dining area features a wooden dining table set for four, with decorative tableware. A blue sofa and a TV are positioned adjacent to a wood-burning fireplace, providing a cozy ambiance. Large windows offer views of the outdoor patio.

Apartment in Basye

Mountain View’s, near Bryce Resort, pet friendly