
Vacation rentals with a patio in Winchester
Find and book unique patio rentals on Airbnb
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 G$10,455 GYD per night before taxes and fees

Verified guest reviews
Over 4,070 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!
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...

Sugar Maple Chalet - 67-Acre Farm
✔ Rustic Luxury: Cozy wood interiors, modern comforts, and charming decor. ✔ 67 Acres of Beauty: Private walking trails and historic outbuildings amid pristine nature. ✔ Stunning Views: Panoramic views by day, star-filled skies by night. ✔ Modern Comforts: Well-appointed kitchen, high-speed Wi-Fi, and more. ✔ Outdoor Clawfoot Tub with Shower: Relax under a maple tree when weather permits. ✔ Whole-House Backup Generator: Reliable backup power keeps the chalet running during unexpected outages.

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

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.

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.

West Virginia's only Airbnb Luxe Property
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.

Ascent at Lost River (cozy cabin with views)
Kick back and relax in this calm, mountain ridge retreat in the wild and wonderful state of West Virginia. From sunrise to sunset, you will have views of the mountains and peaceful quiet time to chill on the porch or by the fire. Enjoy the entire house and exploring the national parks in the area. Check out the cabin on IG at ascentatlostriver to see more photos of Ascent and local recommendations for delicious eats and fun activities.

Guest-Favorite A-Frame with Hot Tub Harpers Ferry
Our guests tell us: "We didn't want to leave." Slip into the salt-water hot tub under the stars, enjoy movie night on the TV screen projector with Bose soundbar system, and watch the A-frame windows fill with morning light. The cabin is nestled in a mountain community in Shannondale — 6 min from the Shenandoah River, 20 min from the Appalachian Trail and Historic Harpers Ferry, and 90 min from DC. ★ 4.95 Guest Favorite · Superhost

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.

Cozy Log Cabin w/views + Hot Tub near Shenandoah
This unique home combines all the best that the Blue Ridge Mountains have to offer. A cozy and rustic log cabin, amazing mountain-top views, easy access to hikes and river activities (either state or national parks), and the best wineries in the area! It's the perfect mix of simple mountain living, but with all of the modern amentities you could want for a comfortable stay. New hot tub was just added.
Popular amenities for Winchester patio rentals
Apartment rentals with a patio

The Lodge at Turkey Creek

The Violet Femme Studio

The 1763 House - Stay in Downtown Shepherdstown

The Downtown Flat at Creekside

Red Fox Retreat

King Bed Apt./Carroll Creek Promenade

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

Spacious apt with King beds in DT Charles Town
House rentals with a patio

Little Red Schoolhouse in Cross Junction

A-Frame Mountain Retreat

Steps to Winery and Battlefield – 1 Acre Retreat

Lux Views of Virginia Mountains, 3 King, 2 Twin

Windy Knoll Adventure | River Front | Hot Tub!

3BR Stone Cabin | Hot Tub + Firepit | Valley Views

Modern Getaway w/Game Room, Hot Tub, Near SNP

Mint Cottage at Little Washington
Condo rentals with a patio

The Cozy Villa

Downtown 1 BR Condo Steps to Everything

Peaceful patio condo

Historic Two Bedroom in Old Town Warrenton

2 Queen & 1 Twin Bed / Mountain & Museum Fun

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

Historic District Downtown Winchester

Mountain View’s, patio sunrises, pet friendly
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$26,137 GYD | G$23,419 GYD | G$25,510 GYD | G$24,674 GYD | G$25,928 GYD | G$26,137 GYD | G$26,137 GYD | G$24,464 GYD | G$23,210 GYD | G$24,883 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 |
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- Family-friendly rentals Winchester
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- Rentals with a patio Virginia
- Rentals with a patio United States
- Luray Caverns
- Stone Tower Winery
- Bryce Resort
- Jiffy Lube Live
- Berkeley Springs State Park
- Cunningham Falls State Park
- Harpers Ferry National Historical Park
- Rock Gap State Park
- Cacapon Resort State Park
- South Mountain State Park
- Whitetail Resort
- Shenandoah River Outfitters
- Hollywood Casino At Charles Town Races
- Reston Town Center
- Sky Meadows State Park
- Greenbrier State Park
- Green Ridge State Forest
- Gambrill State Park
- Bluemont Vineyard
- Antietam National Battlefield
- Weinberg Center for the Arts
- Skyline Caverns
- Dulles Town Center
- Big Cork Vineyards





