Cottage vacation rentals in Leesburg

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Leesburg

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

0 of 0 items showing

1 of 3 pages

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, 370 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 charming stone cottage is set against a backdrop of lush trees and open sky. A gravel path leads to the entrance, with two chairs positioned on the grassy area, offering a serene view of the surrounding nature.

Cottage in Leesburg

4.92 out of 5 average rating, 401 reviews

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!

Guest favorite

A spacious outdoor deck offers sweeping views of the surrounding trees and distant hills. Large glass sliding doors provide access to the interior, enhancing the connection between indoor and outdoor spaces. The deck features a wooden floor, contributing to a natural ambiance.

Cottage in Markham

4.96 out of 5 average rating, 140 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

Cottage in Round Hill Village

4.93 out of 5 average rating, 183 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

Cottage in Bluemont

4.95 out of 5 average rating, 240 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.

Top guest favorite

A sweeping view captures the confluence of rivers surrounded by rolling hills and autumn foliage. The scene includes a quaint town nestled among the trees and a bridge crossing the river, illustrating the natural beauty of Harpers Ferry.

Cottage in Harpers Ferry

4.97 out of 5 average rating, 180 reviews

A little piece of the country in the town

Located in the scenic town of Harpers Ferry, this sunny little cottage is tucked away in a great little neighborhood full of friendly people and backyard chickens. The neighborhood has restaurants, a wonderful bakery, two local bars, and we are a 20 minute walk from historic Harpers Ferry. The cottage is owned by two local old time Appalachian musicians, so you might hear some fiddle tunes drifting through the air if you are deck sitting. Bedroom has a queen bed No cleaning fees

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, 338 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 cats (and 3 kiddos!). Just 3 miles to downtown Leesburg.

Top guest favorite

The exterior of Rose Cottage is surrounded by lush blooming flowers, creating a colorful welcome. A white picket fence borders the entrance, leading to a rustic wooden door framed by a trellis. Sunlight filters through the green foliage overhead, accentuating the charming garden setting.

Cottage in Sperryville

4.98 out of 5 average rating, 117 reviews

Adorable Rose Cottage in Village of Sperryville

Rose Cottage is a quaint one-of-a-kind retreat in the heart of Sperryville - a charming country village offering shops, galleries, eateries, and more. The property has an excellent location, only 1.5 hours from Washington, DC and convenient to Culpeper, Warrenton, Front Royal and Interstate 66. It is approximately 15 miles from Old Rag Mountain and a 15 minute drive to the Shenandoah National Park, which offers an amazing array of waterfalls, canyons, trails, and hikes.

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, 207 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

The quaint cottage entrance is framed by lush greenery and a gently sloping garden. A brick pathway leads to a wooden deck with white railings, while a small pond with natural stones is visible in the foreground, surrounded by various plants.

Cottage in Shepherdstown

4.94 out of 5 average rating, 277 reviews

The GW Hollida Cottage of Shepherdstown

Let time slow just a bit at this unique and tranquil getaway! This recently renovated cottage is situated just behind the GW Hollida house, circa early 1800s. Whether taking a few extra breaths of fresh air on the deck, taking a stroll through the 5 acres of serenity, or kicking back to enjoy some peace and quiet, we are confident you'll love this place as much as we do!

Top guest favorite

Cottage in Martinsburg

4.98 out of 5 average rating, 410 reviews

Last Rodeo Cottage

Our cottage is private where guest can relax; Looking to spend some quiet time out of the city. Close to D.C.and the Historic site of surrounding areas. Close to Charlestown Casinos. Our home is right off I- 81 This cottage is Handicap accessible from private parking to shower and amenities. Lovely park like setting shared with our family pets.

Guest favorite

The exterior of the cottage features a welcoming entrance with a white door and a porch supported by white columns. Symmetrical windows on either side enhance the facade. The garden includes low shrubs, and a gravel pathway leads to the entrance, framed by well-maintained grass.

Cottage in Leesburg

4.93 out of 5 average rating, 229 reviews

The Cottage at Stone Tower Winery

The Cottage at Stone Tower Winery is a fully renovated, one-bedroom house located only an hour from DC, 30 minutes from Dulles Airport, and 15 minutes from Leesburg. The home is perfectly situated to enjoy a peaceful stay in the country and serves as an ideal location to explore the Northern Virginia wine region and historic Loudoun County.

0 of 0 items showing

What guests are saying

Cozy Retreat - Walk to Hunters Head Tavern

4.98 out of 5 average rating, 43 reviews4 months ago

Excellent stay at a super reasonable price for the area over the Thanksgiving holiday. Very cozy, super comfortable and clean, and walkable to shops and restaurants in Upperville. Only a short drive to Middleburg. Highly recommend and would stay again!

Cottage in Upperville

What guests are saying

Chic 3BR home, VA wine country near Harpers Ferry

4.91 out of 5 average rating, 111 reviews10 months ago

We had a blast at this Airbnb! The cottage was extremely cute on the outside, and having the little zipline and firepit was a great addition to our girl's trip. You can tell the host put a lot of effort into her listing, it was a very pleasant stay!

Cottage in Purcellville

What guests are saying

Mountain Top View Spacious Family Cottage

4.81 out of 5 average rating, 147 reviews3 weeks ago

My wife and I stayed at the house for a miniature getaway. Place was very quiet and matched what was described and shown in the pictures. Richard was very communicative and directions to the house were very clear. Place felt like home and was a nice relaxing getaway in the mountains. Would definitely stay there again in the future if the opportunity presents itself. Definitely recommended if you love the outdoors and are looking for a quiet, relaxing getaway into the mountains

Cottage in Harpers Ferry

What guests are saying

NEW * The Getaway Cottage at Rocky Marsh Farm

4.97 out of 5 average rating, 151 reviews3 days ago

The house and property were beautiful, the house was super clean and felt cozy even though it’s new! Check in was really easy and Zeb was quick to respond. Loved being able to sit outside at the fire pit! It was a 10 minute drive to Shepardstown and 30 minutes to Harper’s Ferry so we were able to explore and go to some of the places that Zeb recommended! Highly recommend!

Cottage in Shepherdstown

What guests are saying

Wheatland Spring Farm + Brewery Cottage House

4.97 out of 5 average rating, 125 reviews2 months ago

I recently had the pleasure of staying at an Airbnb located at Wheatland Farm and Brewery, and it was an unforgettable experience! The setting was absolutely picturesque, with sprawling fields and a charming rustic ambiance that made us feel right at home. The accommodations were comfortable and well-appointed, featuring all the amenities we could ask for. The cozy farmhouse vibe made it the perfect retreat from city life.

Cottage in Waterford

What guests are saying

Milton Valley Cottage on Historic Estate Farm

4.98 out of 5 average rating, 106 reviews2 days ago

Kelly’s home was so charming and peaceful! We appreciated all the small touches you don’t find in your average bnb. We loved sitting on the porch and watching the cows over coffee. We liked being near to town but off the beaten path. Will return!

Cottage in Berryville