
Holiday rentals with a patio in Winchester
Find and book unique rentals with patio 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 $64 SGD 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
50 of Winchester holiday rentals include wifi 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 rentals with patio in Winchester
Guests agree: these rentals with a patio 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...

The Cottage at Nestled Inn
Nestled into the Blue Ridge mountains, practically walking distance from Bear Chase Brewery, Twin Oaks Tavern Winery & The Applachian Trail, our home offers you poolside views of our garden, hottub views of the stars, backyard views of our free range chickens & front yard views of our two horses as well as onsite massage therapy, cats & dogs. While being tucked away, we are still just 10minutes from Purcellville or Berryville & 30minutes from Leesburg, Middleburg, Winchester or Harper's Ferry.

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.

Shenandoah Escape ~Sauna ~Walk to SRO ~King Bed
Escape to the beauty of the Shenandoah Mountains and enjoy easy access to the Shenandoah River Outfitters from this custom log cabin in Luray. Relax in the sauna, unwind in the hanging basket chair on the deck, play corn hole in the yard, swing on the under deck swings, or lounge around the fire pit. Spend time kayaking, tubing, or rafting down the Shenandoah River... we are the closest Airbnb to the Shenandoah River Outfitters! The scenery and memories you will make are spectacular!

Riverfront Sauna! Hot Tub! Luxury Romantic Retreat
River views from your cozy king bed or fireside couch, sitting in the hot tub with the sounds of the river just yards away, soaking tub with bath bombs, a chandelier and mood lighting, high end espresso machine and finishes, sound appealing?? Riverside Romance offers all this and MORE! Nestled in the dreamy pines by the river, this couples escape was designed for you and your partner to escape the world and reconnect in Luxury. Surprise your significant other with a getaway to remember!

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!

CloudPointe Retreat
Rare Appalachian Treehouse Gem! Luxurious, one-of-a-kind retreat for couples. Elevated tiny house among the treetops, private parking, plush bedroom, sleek bathroom, beautiful kitchenette, loveseat, lounge, private double-level decks, fireside lounging (wood provided), gas grill, and patio with a hot tub! Surrounded by nature, with wineries, hikes, restaurants and shopping all nearby. Please come and relax and revel in the beauty of nature! 4WD is recommended.

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.
Popular amenities for rentals with patio in Winchester
Flat rentals with a patio

Rustic River Retreat- 2 Bedroom Riverfront Lodging

Private Studio Apartment - Own Entry

Spacious apt with King beds in DT Charles Town

The Downtown Flat at Creekside

Editor’s Suite at Pigeon Hill

Red Fox Retreat

Friendly & luxury (whole private suite)

Private, relaxing, scenic 2 bdrm unit, Sleeps 1-5
House rentals with a patio

Little Red Schoolhouse in Cross Junction

A-Frame Mountain Retreat

Mint Cottage at Little Washington

The Great Escape Lodge ~ Exquisite Mountain Views

Steps to Winery and Battlefield – 1 Acre Retreat

Entire historic stonehouse 1 mi walk Harpers Ferry

Cozy Reliance Retreat with Beautiful Views

Ridgeview Retreat | Views, Pets & Game Barn
Apartment rentals with a patio

Stay 2+Nights, Get 1 Free @ 7 Springs w/ Hot Tub

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

Seven Springs 2 Bedroom Condo

Mountain View’s, patio sunrises, pet friendly
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $161 SGD | $144 SGD | $157 SGD | $152 SGD | $160 SGD | $161 SGD | $161 SGD | $151 SGD | $143 SGD | $153 SGD | $161 SGD | $161 SGD |
| 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
- New York City Holiday rentals
- Philadelphia Holiday rentals
- Washington Holiday rentals
- Pittsburgh Holiday rentals
- Columbus Holiday rentals
- Ocean City Holiday rentals
- Cleveland Holiday rentals
- Raleigh Holiday rentals
- Virginia Beach Holiday rentals
- Niagara Falls Holiday rentals
- Newark Holiday rentals
- Jersey City Holiday rentals
- Rentals with a washing machine and dryer Winchester
- Hotel rooms Winchester
- Flat rentals Winchester
- Rentals with outdoor seating Winchester
- Cottage rentals Winchester
- Fitness-friendly rentals Winchester
- Rentals with a fireplace Winchester
- Apartment rentals Winchester
- House rentals Winchester
- Family-friendly rentals Winchester
- Cabin rentals Winchester
- Rentals with pools Winchester
- Rentals with breakfast Winchester
- Pet-friendly 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
- Harpers Ferry National Historical Park
- Jiffy Lube Live
- 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
- Sky Meadows State Park
- Shenandoah Caverns
- Green Ridge State Forest
- Antietam National Battlefield
- Bluemont Vineyard
- Weinberg Center for the Arts
- Greenbrier State Park
- Skyline Caverns
- Dulles Town Center





