
Holiday rentals with a patio in Winchester
Find and book unique Holiday Accommodation with Outdoor Verandahs on Airbnb
Quick stats about holiday rentals with a patio in Winchester

Total holiday rentals
Explore 50 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at $89 NZD per night before taxes and fees

Verified guest reviews
Over 3,910 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
50 of Winchester holiday 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 Holiday Accommodation with Outdoor Verandahs in Winchester
Guests agree: These Holiday Homes with Outdoor Verandahs 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...

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

Cozy Chalet Near Berkeley Springs & Harpers Ferry
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 !

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.

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!

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.

The Overlook; A Romantic Treehouse for Two
The Overlook welcomes you with stunning views of the Appalachian Mountains and offers luxurious first class amenities! ⛰️✨ Mountain Views 🌄 Private Deck 🌿 Hot tub ♨️ Outdoor TV 📺 Gas Fire Pit 🔥 Large two person egg chair 🪑 Soaking Bathtub 🛁 Luxury tile shower 🚿 Full Kitchen 🍳 King Bed 🛏️ Fast Wifi 💻 100 inch Movie Projector screen 🎬 Bluetooth Mantle Soundbar 🔊
Popular amenities for Winchester Holiday Houses with Outdoor Verandahs
Apartment rentals with a patio

The Downtown Flat at Creekside

Spacious apt with King beds in DT Charles Town

Cozy Downtown Suite + Coworking (3S)

Red Fox Retreat

2BR Suite | 5 min to downtown + JMU | Pet-Friendly

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

Big views! - The Loft at Wildwood

King Bed Apt./Carroll Creek Promenade
Holiday House Rentals with a Verandah

A-Frame Mountain Retreat

Berkeley Springs Jungle Lodge w/ private stream

Mint Cottage at Little Washington

3br/1ba house up to 6 people

Skyline Villa-Views, Wineries, Hot Tub, Nat’l Park

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

Steps to Winery and Battlefield – 1 Acre Retreat

Entire historic stonehouse 1 mi walk Harpers Ferry
Holiday condos with a patio

Terrace Apartment at the Rest PF

2 Queen & 1 Twin Bed / Mountain & Museum Fun

Historic Two Bedroom in Old Town Warrenton

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

Downtown 1 BR Condo Steps to Everything

Historic District Downtown Winchester

Mountain View’s, pet friendly, patio sunrises

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 | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $222 NZD | $199 NZD | $216 NZD | $209 NZD | $220 NZD | $222 NZD | $222 NZD | $207 NZD | $197 NZD | $211 NZD | $222 NZD | $222 NZD |
| 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 |
Destinations to explore
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- Rentals with outdoor seating Winchester
- Rentals with a washing machine and dryer Winchester
- Cottage rentals Winchester
- Fitness-friendly rentals Winchester
- Rentals with a fireplace Winchester
- Hotel rooms Winchester
- Rentals with pools Winchester
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- Family-friendly rentals Winchester
- Pet-friendly rentals Winchester
- Condo rentals Winchester
- Apartment rentals Winchester
- House rentals Winchester
- Cabin rentals Winchester
- Rentals with a patio Virginia
- Rentals with a patio United States
- Luray Caverns
- Stone Tower Winery
- Bryce Resort
- Berkeley Springs State Park
- Cunningham Falls State Park
- Jiffy Lube Live
- Harpers Ferry National Historical Park
- Cacapon Resort State Park
- South Mountain State Park
- Rock Gap State Park
- Whitetail Resort
- Shenandoah River Outfitters
- Reston Town Center
- Hollywood Casino At Charles Town Races
- Gambrill State Park
- Shenandoah Caverns
- Sky Meadows State Park
- Green Ridge State Forest
- Bluemont Vineyard
- Antietam National Battlefield
- Greenbrier State Park
- Weinberg Center for the Arts
- Skyline Caverns
- Dulles Town Center





