Vacation rentals in Leesburg

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Top-rated vacation rentals in Leesburg

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favourite

Home in Leesburg

4.99 out of 5 average rating, 139 reviews

Leesburg Hideaway w/ King Bed + Private Backyard

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

Guest favourite

Treehouse in Waterford

4.94 out of 5 average rating, 594 reviews

Tranquil Treehouse

Nestled on a hillside overlooking the tributary to the Potomac this glammed out cottage has everything you need for a romantic getaway. Immersed just outside the tall glass walls is a private deck overlooking a forest. This property is from our Waterford reservations collection you might get lucky and see a couple of bald eagles on your visit. Enjoy indoor or outdoor shower. The treehouse is completely private and equipped with wifi, kitchen, king bed fire pit nearby and more. Book smart….

Top guest favourite

Apartment in Leesburg

4.99 out of 5 average rating, 172 reviews

The Barn at Belgrove

The Barn at Belgrove. Welcome to a private and quiet escape on a 67 acre manor in Leesburg. A horse property with abundant wildlife offers a peaceful getaway on an historic property. This full apartment is located above the barn. It is convenient to downtown Leesburg, Morven Park, and Loudoun's many wineries, breweries and festivals. Most suitable for adults seeking to relax, recharge, and rekindle in a rustic environment. There is generally very good cell service but there is no Wifi.

Guest favourite

Barn in Leesburg

4.93 out of 5 average rating, 138 reviews

Romantic Barn Loft near Downtown Leesburg!

How about a Summer Escape to the Country? Welcome to Windy Hill Loft! This is a completely unique stay experience in the Loft built inside our Big Red Barn! Imagine relaxing in this charming space all while overlooking our horses, our adorable mini cows AND the mountains in the heart of Virginia Wine Country. Within 2 miles of some of the best wineries in the area and only a 15 min. drive into downtown Leesburg, Windy Hill is the perfect place to relax after a fun day in the Country!

Superhost

Dome in Leesburg

4.82 out of 5 average rating, 125 reviews

Luxe & Picturesque Dome Haven ~ Hot Tub ~ Glamping

Experience Luxury Glamping in Leesburg! Discover the perfect blend of comfort and nature in our charming dome, just minutes from downtown Leesburg. Enjoy modern amenities like split AC/heating, WiFi, a projector, fridge, and coffee maker. Relax in the outdoor jacuzzi, cozy up by the propane fire pit, and unwind under ambient lighting. Explore renowned wineries, Morven Park, and local attractions nearby. A unique, romantic escape awaits—book your unforgettable glamping getaway today!

Guest favourite

Cottage in Leesburg

4.91 out of 5 average rating, 352 reviews

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.

Top guest favourite

Guesthouse in Hamilton

4.99 out of 5 average rating, 151 reviews

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.

Top guest favourite

Home in Leesburg

5 out of 5 average rating, 149 reviews

Downtown Leesburg Cottage. Walk to everything!

Beautiful cottage in Downtown Leesburg! Walkable to all that Downtown has to offer! Across the street from the iconic Mom's Apple Pie and a short walk to restaurants, shopping, breweries and W&OD trail. Just a short drive to many local wineries, wedding venues, hiking and only 20 minutes from the Dulles Airport. Escape for the weekend or week and enjoy this beautiful 2 bedroom/1 bath home. Equipped with the essentials you need for a more than enjoyable stay!

Top guest favourite

Farm stay in Purcellville

4.99 out of 5 average rating, 362 reviews

Cozy Cuddle up on 1700’s Clydesdale Farm

The Hunt Box at Sylvanside Farm is a couples favorite! Cozy bedroom with bay window overlooks the stone barn, Clydesdales field and pond. Full kitchen, full bath and small living room. Enjoy a glass of wine on dock, hike the fields and streams, enjoy the animals, roam the our beautiful 25 acres. Escape the city and relax. Our visitors to date have proclaimed it magical and we hope you agree. In accordance with Airbnb’s policies parties are not permitted.

Top guest favourite

Tiny homes in Purcellville

4.97 out of 5 average rating, 404 reviews

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!

Top guest favourite

Home in Leesburg

4.97 out of 5 average rating, 100 reviews

Quaint Royal Cottage @ Historic Leesburg

Welcome to the Quaint Royal Cottage, a beautifully appointed home nestled in one of Historic Leesburg's most desirable neighborhoods. Just a short stroll away, you'll find an array of dining options ranging from gourmet restaurants to casual eateries, along with numerous brewpubs and vibrant nightlife spots. After a night out, retreat to the serene backyard oasis and relax by the fire pit. Your delightful stay is guaranteed!

Guest favourite

Guesthouse in Paeonian Springs

4.98 out of 5 average rating, 123 reviews

Bear Mountain Cottage

Welcome to Bear Mountain Cottage. This newly built cottage is nestled on a small mountain just under 10 minutes from the edge of downtown Leesburg. Enjoy this beautifully decorated space with all modern amenities. King size bed, open living area, and walk in shower are just a few highlights. Whether you are visiting for a wedding, exploring wine country or in need of a quiet setting, we invite you to enjoy!