
Vacation rentals with a patio in Winchester
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Top-rated patio rentals in Winchester
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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.

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...

The Bella Vista House
This modern cabin offers a beautiful view of the Shenandoah Valley and is a perfect getaway home! To experience an unforgettable moment on the porch, make yourself a cup of coffee and enjoy peace and tranquility. Inside you will find an open floor plan with soaring ceilings, a well-stocked kitchen and an amazing wall of windows! Minutes from the Shenandoah River (w access to road boat ramp), Shenandoah National Park, Skyline Drive, wineries, river sports, horseback-riding, Luray Caverns & more.

Spectacular View, PET FREE, Skylight and Hot Tub
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 peace no train noise unlike old town. Large patio, courtyard, firepit, hammock, "Mind Blowing" 2 person soaking tub. The outdoor space provides private vistas of Shenandoah, moonlit nights, star gazing, or taking in beautiful scenery while enjoying a relaxing shower in our cedar outdoor shower under the sun or stars

Hot Tub!, 2 Fire Pits, Huge Deck, Private orchard!
The home is an adorable cottage perfect for both a romantic getaway or a family/friends retreat. Enjoy views of the small orchard on the 3 acre wooded property from the large deck and two firepits. The Orchard Cottage is a great base to explore local wineries, hiking, and nearby Bryce Resort. Conveniently located 2 hrs from DC, 45 minutes from Harrisonburg, and only 12 minutes from Bayse/Bryce Ski Resort. Only a 15 min drive to I-81 to conveniently access all the Shenandoah Valley has to offer

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

Lost River Hideout
Winter has arrived and we are no strangers to snow. Venture into wild or stay cozy by our fireplace and marvel at nature through the huge living room windows. Beyond the cabin only the vast GW National Forest. Our cabin offers all modern amenities including high speed wifi, central air, and a gourmet kitchen. Keep your eyes open for wildlife. The cabin is a stone throw from lakes and endless trails. Or maybe go skiing? But be warned - you may not wish to leave once you put your feet up!

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.

Kona’s Cozy Cabin • Fireplace, King Bed, Pets OK
🌲 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 Cozy Villa
Home away from home, conveniently located seconds away from Interstate 81 and central to all restaurants and shops! Perfect for a group of traveling friends or a family looking for a peaceful stay. This warm and cozy villa boasts tastefully modern features with 2bdr, 1bth, fully equipped kitchen, living room, dining room, washer/dryer in unit, front and back patio with patio furniture. The home has a driveway so parking is hassle-free! Very quiet and safe neighborhood.

Rustic and stylish mountain getaway
The Little Black Cabin is everything you've been dreaming about for your cozy mountain getaway! Take in sweeping views, curl up by the fireplace, or make s'mores at the fire pit. Whip up a gourmet meal in the small but well-appointed kitchen. Three dining areas offer options for dinner -- or a remote office, thanks to wifi. Sample nearby hiking, yoga, and farmers' market. We're a little rustic (no TV, AC, microwave, laundry or dishwasher) and a lot stylish!

Windy Knoll Adventure | River Front | Hot Tub!
Discover our Black Modern Charm Home, a private retreat atop 35 acres with sweeping mountain and Shenandoah River views. Relax in the hot tub overlooking the river, fish or kayak below, and unwind by the campfire in this peaceful woodland setting. 🌲♨️ Designed for comfort and escape, this modern retreat is perfect for unplugging, reconnecting, and enjoying nature at its finest. Book now for a true mountaintop getaway. ✨
Popular amenities for Winchester patio rentals
Apartment rentals with a patio

Spacious apt with King beds in DT Charles Town

The Downtown Flat at Creekside

Red Fox Retreat

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

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

Southern Charm Getaway in Romney, WV - Sleeps 6

ShenandoahEscape~HotTub~OutdoorCinema~DogFriendly

The Dorothy Historical home in Shepherdstown, WV

Private Cabin Retreat in Lost City, WV

A-Frame Mountain Retreat

Cabin on River with Private Waterfront, Fast Wifi

Entire house up to 6 and 2 pets allowed

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

Downtown 1 BR Condo Steps to Everything

Historic District Downtown Winchester

Mountain View’s, 2 mi. to Bryce, pet friendly

Newly Renovated HUGE condo in 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 | G$21,548 GYD | G$23,431 GYD | G$25,941 GYD | G$24,686 GYD | G$25,941 GYD | G$26,150 GYD | G$26,150 GYD | G$24,477 GYD | G$23,221 GYD | G$25,941 GYD | G$28,242 GYD | G$26,150 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$8,368 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
- Reston Town Center
- Gambrill State Park
- Cacapon Resort State Park
- South Mountain State Park
- Shenandoah Caverns
- Big Cork Vineyards
- Rock Gap State Park
- Appalachian National Scenic Trail
- Shenandoah River Outfitters
- Harpers Ferry National Historical Park
- Jiffy Lube Live
- Hollywood Casino At Charles Town Races
- Cooter's Place
- Museum of the Shenandoah Valley
- Sky Meadows State Park
- Old Town Winchester Walking Mall
- Antietam National Battlefield
- Skyline Caverns




