Holiday houses in Leesburg

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Top-rated holiday rentals in Leesburg

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

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Top Guest favourite

Tiny home in Harpers Ferry

4.98 out of 5 average rating, 123 reviews

Enchanting PET FREE W/Amazing ViewHot Tub Overlook

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. Featuring large patio, outdoor dining area, courtyard, firepit, hammock, outdoor 2 person soaking tub. The outdoor space provides private vistas of Shenandoah, moonlit nights, star gazing, "Mind Blowing" outdoor soaking tub or taking in the beautiful scenery while enjoying a relaxing shower in our all cedar shower room.

Superhost

Cabin in Leesburg

4.94 out of 5 average rating, 374 reviews

100 Acre Wood

🌳100 Acre Wood🌳is the perfect magical getaway🌻our cabin is tucked away in the woods on a 100 acre property in the❤️of historic Loudoun County.Located in the charming village of Lucketts, known for our BEAUTIFUL WINERIES🍷FAMOUS ANTIQUE SHOPS, FINE DINING & CRAFT BREWERIES 🍻The Potomac River, C&O Canal, Appalachian & WO&D Trails, Sugarloaf Mt. & Harpers Ferry are all just a few miles away.Come relax, unwind & enjoy our peaceful woods& wildlife🐾We are approx 1 hour to DC & 1/2 hr to Dulles✈️

Top Guest favourite

Apartment in Leesburg

4.99 out of 5 average rating, 170 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

Farm stay in Round Hill Village

4.93 out of 5 average rating, 412 reviews

The Goat Loft - A Private, Peaceful Getaway!

Private Blue Ridge Retreat – Nature, Hiking, and Relaxation Escape to 13 acres of peaceful woodlands and pasture at the base of the Blue Ridge Mountains. Enjoy the goats from the private deck, perfect for stargazing at night! Nearby, hiking on the Appalachian Trail, cycle scenic routes, or explore historic towns, wineries, and breweries. The Potomac and Shenandoah Rivers offer even more outdoor adventures. A perfect mix of tranquility and adventure, but just minutes from everything!

Superhost

Dome in Leesburg

4.83 out of 5 average rating, 117 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, 347 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

Home in Leesburg

5 out of 5 average rating, 141 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!

Guest favourite

Farm stay in Hamilton

4.95 out of 5 average rating, 223 reviews

Historic Farmhouse in Beautiful Western Loudoun

Historic beautifully restored stone house located on beautiful farm property just outside of Leesburg VA. The house is a perfect spot to unwind, relax, and come explore Loudoun County which is filled with wineries, breweries, farm to table restaurants, hiking trails and more! Beautifully decorated space, king size bed, large comfy couch, dining room and kitchen are a few highlights of the space. This is the entire house. Looking forward to your stay!

Guest favourite

Cottage in Hamilton

4.88 out of 5 average rating, 409 reviews

Robins Nest

Beautiful cottage crafted from all reclaimed materials as with all of our Waterford reservations properties. Open floor plan with high ceilings are sure to impress. The luxury of this cottage cannot fully be felt until your perfect stay. Please don’t book Airbnb and then complain about the fees., That was your choice to use the airbnb platform. When you book any of our properties with Airbnb, we will ensure that you have a fantastic stay.

Top Guest favourite

Guest suite in Leesburg

4.99 out of 5 average rating, 213 reviews

Suite GG ~ Relax & Enjoy

Let this cozy above-garage apartment be your home away from home. Located in Lucketts, VA we are within a short distance to the small artsy town of Leesburg, local wineries, breweries, antique stores, shopping outlets, hiking, biking and canoeing/kayaking on the Potomac River. Our spacious, fully-furnished apartment with private entrance sits above a detached garage and features a lovely raised deck overlooking the back gardens.

Top Guest favourite

Home in Leesburg

5 out of 5 average rating, 108 reviews

Royal Heritage Home @ Historic Leesburg

Welcome to the Royal Heritage Home, 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, 117 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!

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Kick off your hiking boots at these rustic lodgings

Popular amenities for Leesburg holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Leesburg

Guest favourite

Private room in Hamilton

4.95 out of 5 average rating, 107 reviews

Quiet Bedroom in a Charming Neighborhood

JacobRating, 5 stars2 weeks ago

This was a great shared room, close to numerous destination centers. Comfortable room with the listed amenities. We were especially impressed with the massive smart tv. Bathroom was large and easy to use, right next to bedroom. The only thing I will mention is the hot water from the shower has a strong sulfur scent, not a big deal and didn’t depreciate the space but may be important for those with scent sensitivities. I would recommend this place to a friend.

Top Guest favourite

Private room in Hamilton

4.95 out of 5 average rating, 235 reviews

Charming bed/bath w/views & space to telecommute

RichardRating, 5 stars3 weeks ago

I had a wonderful stay. Tracy is a very gracious host. The location is very peaceful and beautiful.

Guest favourite

Private room in Herndon

4.92 out of 5 average rating, 156 reviews

Spacious private room near IAD

MikeRating, 5 stars3 weeks ago

This is always a great place to stay whenever I am in Herndon. Buddy is a terrific and responsive host. The room and bathroom are clean and there is even a common space to stretch out. Always my choice if it is available.

Guest favourite

Condo in Leesburg

4.9 out of 5 average rating, 31 reviews

Entire Condo - Walkable Downtown Leesburg

EliseRating, 5 stars2 weeks ago

Cute little apartment right off King street! Check-in/out was easy, apartment was clean, and we had no issues. Just a quick note that the bathroom is not attached to the studio so walking to and from room is an open staircase to the business below which was never a problem for us! Steve was a great communicator and made sure all was well on our end throughout the weekend. Would highly recommend!

Guest favourite

Private room in Leesburg

4.91 out of 5 average rating, 87 reviews

Serene, Calmative, Scenic

KylieRating, 5 stars4 days ago

Wonderful place to stay! Beautiful neighborhood, super clean, great parking, lots of space. Instructions were easy to follow, host was responsive and easy to get in touch with. I’ve stayed in many Leesburg, VA AB&Bs, this is by far the best one! Highly recommend

Top Guest favourite

Private room in Leesburg

5 out of 5 average rating, 76 reviews

Max & Boo's house

DanielleRating, 5 stars1 week ago

This was the most perfect stay for my boyfriend and I and our puppy. Margaret was super accommodating, greeted us upon our arrival but was not in our space upstairs. Her fenced in yard was exactly was our dog needed! We would definitely stay again!

Top Guest favourite

Barn in Leesburg

4.93 out of 5 average rating, 136 reviews

Romantic Barn Loft near Downtown Leesburg!

ShaneRating, 5 stars1 week ago

The loft was beautiful and in a great location with lots of wineries nearby. Natalie was kind enough to show us her animals which was a highlight of the stay.

Guest favourite