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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, 394 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!

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, 157 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!

A charming outdoor seating area features red wooden chairs and a fire pit, surrounded by lush greenery and pavers. The Cottage, with its welcoming facade and gray metal roof, is visible in the background, offering a cozy retreat in a natural setting.

Cottage in Bluemont

4.95 out of 5 average rating, 256 reviews

Cottage on Horse Farm: Wineries/Breweries, Horses!

**Pool open May 1- Sept 29 ** 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

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

4.97 out of 5 average rating, 167 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.

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, 357 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, 220 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.

A charming cottage is framed by a mature tree with autumn leaves. The exterior is painted in calming blue and white, featuring a welcoming porch supported by columns. A gravel path leads to the entrance, surrounded by vibrant greenery and fallen leaves.

Cottage in Aldie

4.97 out of 5 average rating, 117 reviews

Status House at the Little River Inn

The Patent House is a part of the Little River inn in Aldie, Virginia and we have been in business for 36 years. A full breakfast is included in your stay, we use local meats, eggs and serve everything from French toast, to quiche, to Dutch apple baby. The Patent House is located across the driveway from the Main House where breakfast is served. There is a bedroom with a double bed, a bathroom attached, a living space and a working wood burning fireplace.

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, 440 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.

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, 135 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.

The image presents a bird's-eye view of a bungalow surrounded by lush greenery and vibrant flowering trees. A well-maintained driveway leads to the home, enhancing the peaceful setting in a wooded area. The property is situated amidst rolling hills, offering a serene atmosphere.

Cottage in Leesburg

4.97 out of 5 average rating, 102 reviews

Hilltop Cottage @ Shiloh

Escape to Hilltop, a peaceful estate with rolling hills, ponds, and lush green views. This NEWLY REMODLED Bungalow, part of a charming duplex, features a private entrance and outdoor seating. Refresh your soul or set out on adventures to nearby breweries, wineries, the C & O Canal, and Lucketts Store. Only 11 miles to historic Leesburg and Morven Park, or 15 miles to scenic Frederick, Maryland.

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, 134 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.

The Stoney Cottage is nestled among tall trees, showcasing a charming stone exterior and a sloped roof. A staircase leads to the entrance, with a gravel driveway and a two-car garage visible in the foreground, surrounded by lush green grass.

Cottage in Midland

4.98 out of 5 average rating, 190 reviews

The Stoney Cottage Hideaway

The Stoney Cottage is located on a 20 acre farm in the middle of beautiful Fauquier County. It provides a unique and peaceful getaway while still offering a lot of local attractions. It is conveniently located to many local attractions such as wineries, breweries, Farmers Markets, The Flying Circus air show, Civil War battlefields and the Shenandoah National Park.

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Kick off your hiking boots at these rustic lodgings

Popular amenities for Leesburg cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

A two-story cabin surrounded by lush greenery, featuring a spacious deck illuminated by soft string lights. The hot tub is visible on the deck, and a gravel pathway leads through the serene outdoor space, enhancing the peaceful mountain setting.

Cottage in Harpers Ferry

4.84 out of 5 average rating, 201 reviews

Cozy Mountain Retreat | Hot Tub & Fire Pit & Dogs

The exterior of Longview House reveals a modern two-story design, featuring large glass doors that open to a welcoming entryway. Stone steps lead up to the entrance, surrounded by lush greenery and natural landscaping.

Cottage in Bluemont

5 out of 5 average rating, 8 reviews

Designer Modern Mountain Escape (w/View & Hot Tub)

Aerial view of a home nestled in a densely wooded area, surrounded by trees displaying a range of green and autumn hues. Rolling hills extend into the distance, creating a serene and natural backdrop.

Cottage in Linden

4.74 out of 5 average rating, 46 reviews

New! Family cottage w/ fast WiFi & pet friendly.

Top guest favorite

Cottage in Barcroft

5 out of 5 average rating, 32 reviews

Luxury Cottage | Hot Tub & Quiet Oasis Near DC

Top guest favorite

An outdoor hot tub is shown with a glass of red wine and a single rose placed beside it. A scenic view of rolling fields and trees is visible in the background, with a colorful sunset illuminating the sky.

Cottage in Winchester

4.99 out of 5 average rating, 419 reviews

Uber SXY Private Country Escape! Hot Tub & Views~

The exterior of the house showcases a modern design with a red facade and multiple levels. Spacious decks are present, providing areas to relax and enjoy nature. Large windows reflect the surrounding greenery, while trees create a tranquil environment.

Cottage in Front Royal

4.96 out of 5 average rating, 99 reviews

Country Elegance overlooking the Shenandoah River

A hot tub is situated in the foreground, filled with clear blue water. Nearby, two wine glasses sit beside a bottle of white wine, with a soft glow from string lights illuminating the grapevine arbor in the background. The scene captures an inviting outdoor atmosphere.

Cottage in Boyce

4.95 out of 5 average rating, 120 reviews

Pets? YES! Hot Tub | Fast Wi-Fi | Fire Pit

Top guest favorite

A charming cottage is shown with a blue exterior and white trim. Colorful flowers and greenery surround the entrance, while a stone pathway leads to the front door. The roof is black, and large windows allow natural light to brighten the interior.

Cottage in Bluemont

5 out of 5 average rating, 49 reviews

Bluemont Escape w/Hot Tub: Walk to AppTrail & Brew

Pet-friendly cottage rentals

A bright living area features an orange couch complemented by blue and grey accent chairs. A circular coffee table sits on a patterned rug, surrounded by large windows that provide ample natural light, highlighting the beautiful hardwood flooring. A well-equipped kitchen is visible in the background.

Cottage in Lyon Park

4.8 out of 5 average rating, 270 reviews

Clarendon: Metro Dog-friendly 40" Roku Park Patio

A charming two-story home is set against a colorful twilight sky, featuring a front porch with white railings. Original stonework is visible at the base, surrounded by well-maintained landscaping, including trees and shrubs, contributing to the welcoming exterior.

Cottage in Paris

4.91 out of 5 average rating, 106 reviews

Quaint cottage in historical town of Paris VA!

An inviting front porch features comfortable seating arrangements alongside potted plants. A walkway made of stone leads to the entrance, framed by lush greenery and decorative elements. The soft lighting creates a welcoming atmosphere for relaxation.

Cottage in Marshall

4.92 out of 5 average rating, 107 reviews

Garden Oasis outdoor entertainment at FrogPointe.

A spacious living area is presented with light-colored tile flooring, featuring a large bed with soft bedding. A dark sofa sits near a modern television, and a decorative shelving unit contrasts with the neutral walls. Natural light enhances the inviting environment.

Cottage in Old Town

4.78 out of 5 average rating, 189 reviews

THE PRINCE COTTAGE WITH PRIVATE PARKING GARAGE!!!

A charming exterior of a yellow cottage is framed by lush greenery and colorful flower beds. The entrance features a decorative wrought iron gate adorned with a seasonal wreath, inviting guests into a serene country setting.

Cottage in Middleburg

4.92 out of 5 average rating, 138 reviews

English Cottage

A charming cape-style home is set amidst lush greenery, featuring a welcoming porch with seating. The structure showcases a sloped roof and multiple windows, allowing natural light to fill the interior. A paved path leads to the front entrance, enhancing accessibility.

Cottage in Middletown

4.9 out of 5 average rating, 286 reviews

Charming "Cream of the Crop" Cape ~❤️of Middletown

A charming two-story cottage features a light-colored exterior with decorative shutters. The covered porch offers sleek seating, inviting relaxation. Lush greenery surrounds the home, contributing to its serene setting. The roof is finished with dark metal, enhancing the cottage's overall character.

Cottage in Upperville

4.88 out of 5 average rating, 94 reviews

Cozy Country Getaway in the Heart of Upperville

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

Private cottage rentals

A spacious living area features comfortable seating with plush sofas arranged around a wooden coffee table. The vaulted ceiling showcases exposed beams and a ceiling fan. Light floods in from large windows, complementing the natural wood accents throughout the open layout.

Cottage in Middletown

4.96 out of 5 average rating, 25 reviews

Another Adventure Farm

Top guest favorite

A bright living area features a comfortable gray sofa adorned with decorative pillows. A glass coffee table sits in front of the sofa. Large windows provide natural light and overlook a peaceful outdoor setting, while a small side table complements the space.

Cottage in Middleburg

5 out of 5 average rating, 61 reviews

Middleburg Bliss

Top guest favorite

A rustic wooden cottage with a welcoming front porch is set against a backdrop of lush green fields and rolling hills. The structure features a red metal roof and a stone chimney, complementing the rural landscape. Nearby foliage adds to the serene atmosphere.

Cottage in Delaplane

5 out of 5 average rating, 59 reviews

Moreland Farm Cottage! / 200 Acre Retreat

Top guest favorite

A charming one-bedroom cottage is attached to a historic home, featuring a blue shingle roof and light green exterior. Lush shrubs and neatly trimmed bushes frame the entrance, which is highlighted by a welcoming front door and outdoor lighting.

Cottage in Alexandria

5 out of 5 average rating, 12 reviews

The Colonial Cottage of Alexandria

A spacious outdoor area is showcased, featuring a brick patio with a BBQ grill and a table with chairs. Lush green grass surrounds the space, complemented by trees providing shade. The cottage is visible in the background, blending into the natural setting.

Cottage in Bolivar

4.93 out of 5 average rating, 29 reviews

"The Lovely Cottage"." Your Home, Our Hospitality"

A light blue cottage exterior is visible, featuring multiple windows with black shutters. A wooden staircase leads to the entrance, surrounded by a well-maintained yard with shrubs and flowers. A stone pathway runs along the grassy area in front of the home.

Cottage in Purcellville

4.92 out of 5 average rating, 91 reviews

Beautiful 3 bedroom cottage on 15 private acres.

The interior space showcases a handcrafted totem pole at the center, surrounded by wooden beams and natural light. A cozy seating area is complemented by a small dining table, while a large rug lays over polished wooden floors. Large doors open to scenic views.

Cottage in Delaplane

4.8 out of 5 average rating, 15 reviews

The Tenant House | Entire Property-2BR | Delaplane

The exterior of the cottage features a combination of light-colored walls and a stone facade, surrounded by well-maintained greenery. The spacious yard is complemented by a clear sky and trees lining the property, enhancing the sense of privacy and tranquility.

Cottage in Delaplane

4.83 out of 5 average rating, 64 reviews

Wine Country Getaway on 21 Acres

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