Cottage vacation rentals in Leesburg

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Top-rated cottage rentals in Leesburg

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Top guest favorite

A tranquil pool area is surrounded by lush greenery and vibrant flowers. The charming cottage, featuring a welcoming porch, is visible in the background under a bright blue sky. The clear water of the pool reflects the sunlight, inviting relaxation.

Cottage in Hamilton

4.95 out of 5 average rating, 388 reviews

*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!

Guest favorite

A spacious deck offers unobstructed views of rolling hills and valleys, accented by vibrant autumn foliage. The sky is expansive, displaying soft clouds and blue tones. A sleek railing encircles the deck, enhancing the serenity of the natural landscape.

Cottage in Markham

4.96 out of 5 average rating, 151 reviews

Sunrise Cottage in Wine Country

The place for nature lovers and the audiophile! Newly renovated cottage with queen bed and queen sleeper sofa! Situated on five acres, at Sunrise Cottage you can see no other dwellings except those in the valley far below. Lay in bed and watch the sun rise from the East. 60 mile views with a monarch waystation off the deck. Relax in the hot tub or sit around the fire pit. Bathroom has a spa feel with rainfall showerhead. Close to Marriott Ranch for horse trail rides and surrounded by wineries!

Guest favorite

A charming cottage exterior is showcased with two large, arch-top windows above a spacious garage. The garage doors feature red barn-style accents, framed by neatly landscaped gardens and gravel pathways. A wooden staircase leads to an upper-level entry, set against a backdrop of lush greenery.

Cottage in Round Hill Village

4.92 out of 5 average rating, 193 reviews

Best Countryside Retreat & No Cleaning Fees EVER

Luxurious & cozy cottage, nestled in Virginia's wine country. With a gas fireplace, amazing beds & linens, gourmet kitchen with EVERYTHING and the great hospitality of owners Jennifer and Eric, you will have a premier visit! Self check in anytime and we are on the 26 acre property for 24/7 service. Beautiful vistas, wineries, and activities, over 200 five-star reviews (Airbnb& VRBO) max privacy and convenience. Relax in our tranquil setting while enjoying all the delights of the region!

Guest favorite

A covered outdoor patio is visible, featuring two wicker chairs with cushions and surrounded by planter boxes filled with flowers. A view of well-maintained greenery and a gravel area highlights the peaceful outdoor setting.

Cottage in Marshall

4.92 out of 5 average rating, 101 reviews

Garden Oasis outdoor entertainment at FrogPointe.

Nestled in between The Plains and Middleburg, this charming cottage is ready to help you relax. Perfect for family and friends during horse events nearby, like Gold Cup, Middleburg Film Festival, Christmas in Middleburg, Twighlight Polo, and much more. Fully functional kitchen with all you could need to cook a meal, fully furnished, indoor and outdoor dining, two large modern bathrooms, and internet / movies for a calm night in. This property stands out for its limitless outside fun!

Top guest favorite

The exterior of a two-story cottage is presented, featuring a blend of dark green siding and stone accents. Large windows are illuminated, highlighting a welcoming entrance. Surrounding trees are bare, indicating the season, while a spacious yard of grass and earth is visible in the foreground.

Cottage in Shepherdstown

4.98 out of 5 average rating, 160 reviews

NEW * The Getaway Cottage at Rocky Marsh Farm

Welcome to The Getaway Cottage, a charming two-bedroom, two-bath home nestled in a peaceful country setting, located just 3.5 miles from Shepherdstown. Our location offers easy access to all the exciting activities and attractions the eastern panhandle has to offer, enjoy a short country side drive to dining, shopping, hiking trails, white water rafting and kayaking adventures. The historic town of Harpers Ferry is a short 25-minute drive away, and 15 minutes to Antietam Battlefield.

Guest favorite

The cottage is a charming two-story building, featuring a dark exterior with large windows. A welcoming porch is accented by steps leading to the entrance, and a stone pathway guides through the lush green yard, surrounded by trees.

Cottage in Leesburg

4.91 out of 5 average rating, 350 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 favorite

The charming exterior of the cottage is shown, featuring a light-colored facade with multiple windows. A welcoming front door is visible, surrounded by vibrant flowers and greenery. A small stone walkway leads to a patio area with wooden seating, overlooking the lush yard.

Cottage in Bluemont

4.96 out of 5 average rating, 215 reviews

The Cottage at Stonecroft

Circa 1902, the Cottage is nestled at the foot of the Blueridge Mountains. The location will put you in touch with the history of the area, antique shops, wineries/breweries and nearby hiking. 2 bedrooms and bath upstairs; living room, dining table and full kitchen on main level (note ceilings in living/dining room are 6'3"). Wifi, fire pit and small charcoal grill. Absolutely no pets/animals. The property has video security system on the exterior of the property only.

Guest favorite

A cozy living area features a comfortable sofa with decorative pillows, positioned near large windows that allow natural light to fill the room. A wooden coffee table sits in the center, complementing the rustic beams and warm wood flooring, while a mirror adds depth to the space.

Cottage in Hamilton

4.88 out of 5 average rating, 411 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.

Guest favorite

A spacious room features a custom wood bed with light bedding and natural elements. The wooden ceiling beams provide an open feel, while soft light enters through multiple windows. A cozy sitting area includes a couch and side tables, enhancing the peaceful ambiance.

Cottage in Leesburg

4.92 out of 5 average rating, 430 reviews

Romantic Stone Cottage Circa 1869-75 acres to Hike

Plan a relaxing getaway at our Stone Cottage, just 15 minutes from Leesburg and under 90 minutes from D.C. Nestled next to a hidden state park with peaceful walking trail, this hilltop retreat offers both seclusion and convenience. Enjoy a custom king bed, inviting interior, and close to many top wineries, breweries, and restaurants. Whether you're here for a wedding, wine tasting, or quiet escape, the Stone Cottage is your perfect getaway.

Guest favorite

The cottage features a charming exterior with a red metal roof and a welcoming porch, supported by white columns. A large tree provides shade, and potted plants are positioned on the porch. The surrounding lawn is well-kept, adding to the inviting appearance of the home.

Cottage in Waterford

4.96 out of 5 average rating, 134 reviews

Wheatland Spring Farm + Brewery Cottage House

The charm of yesterday with the amenities of today. The private cottage house is appointed with a premium queen size bed, 1.5 baths, and a clothes washer and dryer. The full kitchen includes: oven, stove, microwave, full size refrigerator, dishwasher, and cookware. Guests enjoy scenic views of the 30 acre Wheatland Spring property. A romantic getaway or longer term stay. Just a 100 yard walk from our on-farm brewery.

Top guest favorite

A view of the Creekside Cottage framed by trees, with soft string lights illuminating the outdoor area. A serene creek reflects the surrounding greenery, while the cottage, with a welcoming porch, is nestled among lush grass and foliage, creating a peaceful natural environment.

Cottage in Shepherdstown

5 out of 5 average rating, 110 reviews

The Creekside Cottage: Downtown | Pet-Friendly

Welcome to the Creekside Cottage, a 2 bedroom/1.5 bathroom spacious home, offering a secluded escape by the creek yet just a short stroll through the gardens of Shepherdstown to shopping and dining. Perfect for getaways, family visits, or university stays, this Creekside Cottage offers a roomy interior, cozy living room, modern kitchen, fire pit, and a private patio & porch to be enjoyed along the Town Run.

Top guest favorite

The historic cottage is framed by lush greenery, featuring a welcoming porch with hanging planters. A dark metal roof complements the light-colored siding, and a gravel pathway leads to the entrance. The structure displays traditional craftsmanship with a covered porch and a well-maintained appearance.

Cottage in Bluemont

5 out of 5 average rating, 129 reviews

Snickers Gap Cottage

Historic cottage nestled in the foothills of the Blue Ridge Mountains, minutes from multiple breweries, wineries, hiking and biking trails, and the Shenandoah river. At just 40 miles west of Washington DC it’s the perfect weekend getaway to the country! We are known for our miles and miles of beautiful country roads. Come spend a weekend (or more!) and get lost in Loudoun.