
Holiday rentals with outdoor seating in Leesburg
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Leesburg
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

*Cottage @ Firefly Cellars* VA Wine Country escape
The Cottage at Firefly Cellars is a private, tranquil escape on the tasting room property. Come enjoy the private pool (in summer months), walk the property with a glass of wine, enjoy views of the neighboring horses, hop to local wineries, or just sit back and enjoy all the cottage has to offer. The cottage is meticulously maintained, beautifully designed, and you will feel at home the moment you walk through the doors. Perfect for a couple, or an individual looking to escape from busy life!

Entire Home in Leesburg – King & Queen Bed +Yard
Escape to this light-filled two bedroom, one bathroom bungalow located minutes from the heart of Leesburg's historic district. Just a short drive from unique shops, restaurants, and outdoor activities. This is the perfect home base whether you're in town for a weekend getaway or an extended stay. Located near the W&OD Bike Trail, Birkby House, Morven Park, breweries, wineries,and Rust Manor. We're excited to host you in our little slice of Leesburg charm! Bikes included: 1 mtn. & 1 cruiser

'Waterfront' on 1796 Historic Farm
Feel refreshed when you stay in this rustic gem! The Springhouse is nestled in the rolling hills of Northern Virginia’s Wine Country! Originally constructed in the early 1800's, the structure was built over a natural spring that was used for refrigeration. Water from the spring maintains a constant cool temperature throughout the year while also filling a pond. The original stone well, channel and stone flooring are all intact for guests to explore and experience how our ancestors lived.

Luxury Mountain Getaway: Sunsets, Wines & Views
Celebrate your special moment in chic elegance and 5-star amenities for adult couples only. You deserve the Sunset Rouge. It's a destination in a relaxed and romantic setting to escape anxiety of kids, city, and work. Let the fun décor and panoramic views inspire the writer and artist within. During the day, take flight with eagles at eye level. At night, gaze into the heavens to catch a falling star. Within 2 miles is Lake Shannondale with beach access provided by the Mountain Lake Club.

Ashburn Manor: 1920’s Farmhouse
Take advantage of this unique opportunity to stay in a beautiful,historic home right in the heart of old Ashburn. Just a quarter mile from the W&OD bike trail, walking distance to several shops/restaurants, 10 min. from Dulles Airport and the metro (easy access to DC), and at the edge of Loudoun County’s vast wine region. The home has been updated with all modern amenities for your comfort. Enjoy BBQ on the patio, books on the sun porch, or coffee on the deck. Peace and serenity await.

Hope Flower Farm Winery Cottage
Welcome to Hope Flower Farm & Winery! This charming 3-bedroom, 1-bath cottage is the perfect retreat for those seeking a peaceful getaway in the heart of Loudoun County wine country. The cottage features a kitchen, cozy living room, and a screened-in porch perfect for enjoying your morning coffee or an evening glass of wine. The cowboy cauldron is the perfect spot for roasting marshmallows or enjoying a cozy fire. Come experience the beauty and tranquility of Hope Flower Farm & Winery.

The Forge on Sunnyside Farm
Sunnyside Farm offers a luxurious stay in a beautifully restored historic forge. You’ll be greeted by the farm’s delightful hosts, Jimmy and Dean, two friendly Potbelly pigs. Beautiful cows forage right outside your door. The Forge features exposed wooden beams, brick walls, and cozy furnishings. The interior is designed with plush bedding, a fully equipped kitchen, and spacious living reminiscent of yesteryear. Breweries, wineries and famous antique stores nearby offer entertainment.

The Cottage at Forest Hills Farm
Beautiful one bedroom, one bath cottage on a picturesque 14 acre farm just outside of downtown Leesburg. Nestled in close to local vineyards, this charming, free-standing cottage is yours and perfect for a weekend getaway or alternative to a hotel. Enjoy the fresh air, beautiful views, and peace and quiet on our little farm. Wander the property and say hello to our donkey, mule, Long Horn cows, goats, chickens, and 3 barn cats (and 3 kiddos!). Just 3 miles to downtown Leesburg.

Hummingbirds Hideaway Treehouse
Come experience the magic of being among the treetops at our newly built treehouse. Whether you are seeking a romantic getaway, peaceful retreat, or family fun our little slice of heaven will offer you an unforgettable stay. Features large windows for stunning views of the surrounding woods and very detailed woodwork. 2 bedrooms with king beds, open living space with full kitchen and bathroom will be sure to impress. Please Please Please message us prior to booking

Trailside Chalet (A storybook chalet with hot tub)
The Trailside Chalet is situated on the W and OD Trail, halfway between Leesburg and Purcellville, Va - an ideal base location for visiting wineries, breweries, and the pastoral countryside of Loudoun County. The chalet will put you just steps from the trail for walking/cycling/horseback riding. Relax and enjoy the amenities of one-of-a-kind interior including wood burning fireplace and peaceful surroundings with hot tub. A perfect getaway for a couple or family.

Historic Downtown Home | Walk to Shops + Fire Pit
Stay in the heart of Historic Downtown Leesburg — just steps from restaurants, boutiques, brewpubs, and nightlife. This beautifully updated 3-bedroom, 3-bath home is perfect for wedding weekends, family visits, and girls’ getaways. With multiple gathering spaces, a fully equipped kitchen, and a private backyard fire pit, it’s designed for connection, comfort, and memorable evenings together. Walk everywhere by day. Relax together by night.

Tiny House near Purcellville
Nestled in the heart of Purcellville is a tiny home with a ton of charm. Less than 5 miles from vineyards, LOCO ale trail breweries, cideries, WO&D bike trail & 20 min to historic Leesburg, the Shenandoah river & Appalachian Trail. Our tiny house is a bit larger w/ 2 bedrooms, full kitchen & bath, family room & cozy front porch with private parking. Enjoy a remote work getaway, (our broadband is about 8-10Mbps) relax & enjoy LOCO living!
Popular amenities for Leesburg outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Best beds ever Movie Rm Spa Tub Lux Spring flowers

Eclectic & Romantic - Walk to Historic Downtown!

Middleburg/Upperville-Stunning,renovated cottage

Private 3BDR, Spacious 1LVL Home, Mins to Airport

Modern Home on Middleburg Equestrian Farm

Historic Tip of the Hill, Purcellville, Virginia

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

The Inwood House- easy on/off I-81
Apartment rentals with outdoor seating

The Boundary House Apartment

Hickory Haven •1B King •Bsmt Apt •Clean •LG

Great Location w/ Cozy Atmosphere

A Great Getaway — Foxglove Retreat

Secluded Country Guest Suite Near Harpers Ferry

Rose End

The Lodge at Turkey Creek

Downtown Frederick Modern Studio
Condo rentals with outdoor seating

Modern, spotless 1br for families or work

2 Queen & 1 Twin Bed / Mountain & Museum Fun

Historic Two Bedroom in Old Town Warrenton

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

Bijou Space in Downtown Bethesda

Beautiful 2BR/1BA Renovated Condo near DC

BRIGHT 1 BD w/ LARGE BALCONY in PRIME BETHESDA LOC

The Daisy in Historic Occoquan (Mins to DC)
When is the best time to visit Leesburg?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $263 AUD | $288 AUD | $292 AUD | $292 AUD | $292 AUD | $294 AUD | $289 AUD | $292 AUD | $307 AUD | $311 AUD | $343 AUD | $321 AUD |
| 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 holiday rentals with outdoor seating in Leesburg

Total holiday rentals
Explore 20 holiday rentals in Leesburg

Nightly prices starting at
Leesburg holiday rentals start at $73 AUD per night before taxes and fees

Verified guest reviews
Over 1,540 verified reviews to help you choose

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

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
20 of Leesburg holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Leesburg rentals

4.9 Average rating
Leesburg stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with outdoor seating Loudoun County
- Rentals with outdoor seating Virginia
- Rentals with outdoor seating United States
- Georgetown University
- National Mall
- Walter E Washington Convention Center
- Nationals Park
- The White House
- District Wharf
- National Museum of Natural History
- Capital One Arena
- Liberty Mountain Resort
- National Museum of African American History and Culture
- Stone Tower Winery
- Arlington National Cemetery
- Howard University
- Washington Monument
- Georgetown Waterfront Park
- National Harbor
- Cunningham Falls State Park
- Smithsonian American Art Museum
- Great Falls Park
- Six Flags America
- The Pentagon
- Lincoln Park
- Library of Congress
- The Anthem




