Cottage vacation rentals in Leesburg

4.95 out of 5 average rating, 379 reviews

A glass filled with red wine sits beside an unopened bottle, positioned on a textured wicker table. Behind, a sparkling pool with a mosaic tile border glimmers in natural light, surrounded by greenery and vibrant blooms.

Cottage in Hamilton

*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!

4.92 out of 5 average rating, 417 reviews

The spacious room features a king-size bed with a wooden headboard and decorative pillows, flanked by two windows allowing natural light. A wooden dresser and a TV entertainment unit are positioned nearby, with rustic wooden beams enhancing the ceiling's charm.

Cottage in Leesburg

Romantic Stone Cottage Circa 1869-75 acres to Hike

Plan a getaway in our newly renovated Stone Cottage nestled on hilltop just 15 minutes from Leesburg & less than 90 minutes from DC. The property adjoins next to a hidden state park, not on the map with gentle hiking trails. Secluded location however 10 min to some of the areas finest wineries & breweries. Custom-made king-size bed and fresh interior, are sure to impress . So whether you are visiting for a wedding, exploring wine country or in need of a quiet setting, we invite you to enjoy!

4.96 out of 5 average rating, 147 reviews

A spacious living area features large glass doors presenting expansive views of rolling hills. Natural light illuminates the space, highlighting a wooden table with candles and a cozy seating area with a comfortable chair positioned for enjoying the scenery.

Cottage in Markham

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!

4.96 out of 5 average rating, 180 reviews

Cottage in Sharpsburg

On the C&O Canal/Potomac River

Located just steps away from Dam #4 on the C&O Canal / Potomac River. (marker 84.6) Perfect for a getaway or romantic weekend. Hike/bike the C&O Canal, bring your kayak/canoe/bikes, fish or swim in the river. Sit on the porch and listen to the rumble of the water falling over the dam. Local lore is this was the home of a canal lock keeper or the gate house keeper. Secluded location away from town. NOT A PARTY HOUSE/owner on site in garage apartment. Inquire if a blocked day is available.

Cottage in Round Hill Village

Vast green vineyards stretch out across rolling hills under a soft sky. Neat rows of grapevines lead the eye through the landscape, which is framed by distant mountains and a charming structure. Pathways meander through the fields, illustrating the rural tranquility of the region.

4.93 out of 5 average rating, 188 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!

4.95 out of 5 average rating, 244 reviews

Cottage on Horse Farm: Wineries/Breweries, Horses!

**Pool open May1- Sept 14. PRIVATE 3 hours pool time daily. Plus private patio, grill and fire pit! Horses outside every window! The Cottage is located on a 230 acre horse farm. Red Gate Farm is a full-service, upscale equestrian farm, containing the Cottage, original farm house and 50 horses & ponies. Convenient to Middleburg and Purcellville, you are surrounded by mountains, wineries, breweries, and hiking, with horses right at your doorstep. All in the beautiful town of Bluemont.

4.91 out of 5 average rating, 111 reviews

A historic stone house features blue shutters and a vibrant blue door. A charming fountain is centrally located in a landscaped garden, surrounded by blooming lavender and manicured grass. Outdoor seating is available, providing a welcoming setting for relaxation.

Cottage in Purcellville

Chic 3BR home, VA wine country near Harpers Ferry

Escape to our charming 1900s historic chic retreat, nestled in the heart of VA wine country. Just a stone's throw from Harpers Ferry and the Shenandoah River, our location is perfect for those who love both the refined taste of wine and the thrill of outdoor adventures. Indulge in activities like kayaking, white water rafting, canoeing, and hiking, or explore the local vineyards and breweries, all set against the backdrop of stunning mountain scenery. Note: Route 340 is now open!

4.91 out of 5 average rating, 345 reviews

Cottage in Leesburg

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.

Two wooden adirondack chairs are positioned around a stone fire pit in a grassy area. The background showcases a landscape of rolling fields and trees, with distant views of horses grazing. The setting provides a peaceful spot for outdoor relaxation.

4.96 out of 5 average rating, 212 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.

4.95 out of 5 average rating, 131 reviews

A picturesque tree-lined driveway is adorned with blooming cherry blossom trees, creating a vibrant canopy of pink petals. The path is framed by lush greenery and a wooden fence, leading to a serene ambiance that invites peaceful walks.

Cottage in Waterford

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.

An inviting porch is presented with wooden flooring and a ceiling supported by white beams. Two wicker chairs are placed on one side, complemented by decorative pillows. Hanging ferns add a touch of greenery, while a wreath decorates the wall nearby.

5 out of 5 average rating, 124 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.

A white picnic table with attached benches is placed on a covered porch. Lush greenery can be seen in the background, providing a serene view. A small potted plant sits at the center of the table, enhancing the inviting outdoor dining space.