
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.

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.

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.

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...

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

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.

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 !

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

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.

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!

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 Winchester patio rentals
Apartment rentals with a patio

Rustic River Retreat- 2 Bedroom Riverfront Lodging

Private King Basement Suite

Red Fox Retreat

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

Charming Historic Downtown Apartment…The Fox’s Den

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

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

King Bed Apt./Carroll Creek Promenade
House rentals with a patio

Day Street - Walk to Harpers Ferry NP

Southern Charm Getaway in Romney, WV - Sleeps 6

Private Country Club Home

A-Frame Mountain Retreat

Cabin with Private Waterfront, On River, Fast Wifi

Mountain Church Cottage

Peaceful Waterfall House is waiting for you.

Steps to Winery & Battlefield-Pvt Acre w/ Hot Tub!
Condo rentals with a patio

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* Buccees

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

The Room with the Views!

Downtown 1 BR Condo Steps to Everything

Historic District Downtown Winchester

Casa 1776 - Spacious Apartment | Heart of Downtown
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R1,768 ZAR | R1,922 ZAR | R2,128 ZAR | R2,025 ZAR | R2,128 ZAR | R2,145 ZAR | R2,145 ZAR | R2,008 ZAR | R1,905 ZAR | R2,128 ZAR | R2,317 ZAR | R2,145 ZAR |
| 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 50 vacation rentals in Winchester

Nightly prices starting at
Winchester vacation rentals start at R515 ZAR per night before taxes and fees

Verified guest reviews
Over 3,900 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 fireplace Winchester
- Rentals with a patio Virginia
- Rentals with a patio United States
- Luray Caverns
- Stone Tower Winery
- Cunningham Falls State Park
- Whitetail Resort
- Shenandoah Valley Golf Club
- Gambrill State Park
- Cacapon Resort State Park
- Berkeley Springs State Park
- Bryce Resort
- Creighton Farms
- Robert Trent Jones Golf Club
- South Mountain State Park
- River Creek Club
- Notaviva Vineyards
- Sly Fox Golf Club
- Bowling Green Country Club
- Dinosaur Land
- Reston National Golf Course
- Twin Lakes Golf Course
- JayDee's Family Fun Center
- Warden Lake
- Herndon Centennial Golf Course
- The Golf Club at Lansdowne
- Whiskey Creek Golf Club




