
Vacation rentals with a patio in Winchester
Find and book unique patio rentals on Airbnb
Top-rated patio rentals in Winchester
Guests agree: these patio rentals are highly rated for location, cleanliness, and more.

COZY+SEXY 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...

Modern A-Frame w/ Hot Tub, Sauna & Stunning Views
Escape to Hiya Cabin, the ultimate getaway to unwind, celebrate, or simply embrace some peaceful solitude. This stunning A-frame offers breathtaking Blue Ridge Mountains views, a private hot tub, and a soothing barrel sauna. Inside, a stylish and cozy retreat awaits with a plush king bed, a fully equipped kitchen, board games, Xbox, EV charge. Spend your evenings by the fire pit, enjoying the mountain air and starry sky. Minutes from Luray Caverns, Lake Arrowhead, Shenandoah National Park & more

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 two 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

Shenandoah Riverfront and Mountain View Cottage
The Misty River Cottage is located on one of the seven bends of the Shenandoah River and at the base of the Massanutten Mountain. It was designed, built and furnished with the goal of being one of the nicest options in the Shenandoah Valley. With views of the river and mountains from every room. Ensuite bathrooms in each of the two bedrooms. A custom built bunk bed for larger groups. Heated floors, spectacular outdoor space and direct river access all within a short drive to Woodstock.

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 !

Cozy Secluded A-Frame Cabin Retreat
Visit us on IG @almostheavenwvcabin for the latest photos and cabin moments! Welcome to Almost Heaven Cabin, our beloved A-frame escape tucked away on a private, wooded acre in the heart of the Sleepy Creek Wildlife Management area. Surrounded by 23,000 acres of protected wilderness, this cabin was created as a peaceful family retreat from city life-yet it's just a scenic 1.5-hour drive from DC and Baltimore. Expect quiet mornings, fresh mountain air, and a true West Virginia getaway.

Kona’s Cabin • Fireplace, King Bed, Pets Welcome
🌲 Welcome to Kona’s Cabin — Your Cozy Shenandoah Escape Unplug, unwind, and settle into Kona’s Cabin, a private and pet-friendly retreat just minutes from Shenandoah National Park, historic downtown Winchester, hiking trails, wineries, and breweries. The cabin features an open living area, cozy fireplace, and a well-equipped kitchen for all your cooking needs. Kona’s Cabin is a cozy abode that’s perfect for couples, solo travelers, or a peaceful weekend getaway with your pup 🐾.

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!

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.

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.

The Sparrow Luxury A-Frame w/Hot Tub in Shenandoah
Escape to The Sparrow, a newly built luxury A-Frame nestled in Virginia’s Shenandoah Valley, just a scenic drive from DC. This modern retreat features an African-inspired design, two bedrooms, a full kitchen, a fireplace, a private hot tub, a deck, a workspace, 4K TVs, and a PlayStation 5. Minutes from Luray Caverns, Skyline Drive, and Shenandoah National Park, it’s the perfect base for unforgettable adventure and relaxation.

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!
Popular amenities for Winchester patio rentals
Apartment rentals with a patio

Downtown Suite with Outdoor Terrace

Rustic River Retreat- 2 Bedroom Riverfront Lodging

Spacious apt with King beds in DT Charles Town

The Downtown Flat at Creekside

Red Fox Retreat

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

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

1 be/1 ba w/patio & free parking.
House rentals with a patio

Stoney Spring Overlook

ShenandoahEscape~HotTub~OutdoorCinema~DogFriendly

The Emerald Roof, Historic Home Downtown Frederick

Mint Cottage at Little Washington

Indoor Heated Pool~EV- Arcade~Fire Pit-WIFI-VIEWS!

Stylish & Spacious House by Dulles Airport

Steps to Winery & Battlefield – 1 Acre Retreat

Spring flowers, spa tub movie room, best beds ever
Condo rentals with a patio

SlopeSide

Terrace Apartment at the Rest PF

2 Queen & 1 Twin Bed / Mountain & Museum Fun

Historic Two Bedroom in Old Town Warrenton

3 BR, 3 bath, BWC, EMU, JMU, 1-81 *WIFI* Buc-ee's

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

Downtown 1 BR Condo Steps to Everything

Historic District Downtown Winchester
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$21,537 GYD | G$23,419 GYD | G$25,928 GYD | G$24,673 GYD | G$25,928 GYD | G$26,137 GYD | G$26,137 GYD | G$24,464 GYD | G$23,210 GYD | G$24,882 GYD | G$26,137 GYD | G$26,137 GYD |
| Avg. temp | 1°C | 3°C | 7°C | 13°C | 18°C | 23°C | 25°C | 24°C | 20°C | 14°C | 8°C | 3°C |
Quick stats about vacation rentals with a patio in Winchester

Total vacation rentals
Explore 40 vacation rentals in Winchester

Nightly prices starting at
Winchester vacation rentals start at G$8,364 GYD per night before taxes and fees

Verified guest reviews
Over 3,810 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
40 of Winchester vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Winchester rentals

4.9 Average rating
Winchester stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with a patio Virginia
- Rentals with a patio United States
- Whitetail Resort
- Luray Caverns
- Stone Tower Winery
- Bryce Resort
- Cunningham Falls State Park
- Berkeley Springs State Park
- Gambrill State Park
- Cacapon Resort State Park
- South Mountain State Park
- Jiffy Lube Live
- Sky Meadows State Park
- Shenandoah River Outfitters
- Harpers Ferry National Historical Park
- Green Ridge State Forest
- Big Cork Vineyards
- Cooter's Place
- Rock Gap State Park
- Bluemont Vineyard
- Antietam National Battlefield
- Reston Town Center
- Skyline Caverns
- Old Town Winchester Walking Mall
- Museum of the Shenandoah Valley
- Shenandoah Caverns




