Cottage holiday rentals in Loudoun County

4.95 out of 5 average rating, 412 reviews

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

*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!

4.98 out of 5 average rating, 236 reviews

A quaint cottage is nestled among manicured gardens and trees. The exterior features a simple white facade, a sloped metal roof, and a large front door, all framed by lush greenery and shrubbery. Natural light gently highlights the surroundings.

Cottage in The Plains

The Cottage on Main -Virginia Wine & Horse Country

The Cottage on Main, originally built around 1840 recently underwent a full renovation! Walk to the restaurants and shops of The Plains or explore the quaint towns of Marshall, Middleburg, Warrenton, Upperville with just a few minutes drive. This one bedroom, 1 bath cottage with full kitchen, living & dining area has everything you need for a weekend getaway or extended stay. The Plains is home to Gold Cup & many other equestrian events, amazing dining & shopping and the Virginia wine country!

The exterior of the stone cottage showcases a blend of natural rock and wood. A porch extends from the cottage, providing scenic views of the rolling landscapes and greenery. Two small evergreen trees frame the view, complementing the tranquil setting.

4.98 out of 5 average rating, 521 reviews

The Stone Cottage at Bluemont Vineyard

The cozy, stone, studio cottage is secluded in the vines & orchards of Bluemont Vineyard. ~ Spectacular sunrise views of Virginia Wine Country ~ Stone walls built from rock found on the vineyard property ~ 5 minutes to Dirt Farm Brewing, Henway Hard Cider ~ 10 minutes to local dining & shopping ~ Over 40 other vineyards to visit within an hour's drive ~ Great Appalachian Trail hiking 10 minutes away ~ River tubing on the Shenandoah 20 minutes away at Watermelon Park

4.99 out of 5 average rating, 150 reviews

A well-appointed kitchen features a central island with a marble countertop, surrounded by wooden cabinets and modern appliances. Natural light floods in through large windows, illuminating the dining area with a small table and four chairs. A patterned rug adds warmth to the wooden flooring.

Cottage in Berryville

Guest Cottage on Historic Estate & Cattle Farm

Fully restored c.1900 farm house on 190 acre estate, ~1 hr from D.C. Cottage is situated at end of a farm road (past the main house and barns), very private w/ creek and cows right outside. Enjoy walks on the farm, local hikes, breweries & wineries, pick-your-own fruit farms, tubing on the Shenandoah, restaurants, antique shops, and more. 1 queen bdrm and bath on 1st flr, 2nd queen bdrm & loft with twin beds on 2nd flr. wifi, fire pit, small grill. Over 25 only, Max 4 adults. 1 SMALL DOG ONLY.

4.9 out of 5 average rating, 125 reviews

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

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. Please be mindful this property is near a train track, charming!

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.

4.95 out of 5 average rating, 270 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.

Cottage in Round Hill Village

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.

4.92 out of 5 average rating, 211 reviews

Private 24-Acre Countryside Retreat - No Fees!

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 250 five-star reviews (Airbnb& VRBO) max privacy and convenience. Relax in our tranquil setting while enjoying all the delights of the region!

4.91 out of 5 average rating, 386 reviews

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

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.

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.

4.96 out of 5 average rating, 243 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.

4.89 out of 5 average rating, 101 reviews

The charming exterior features a light-colored house with a metal roof, framed by well-kept greenery. A bold blue door provides an inviting entrance, while white window shutters accentuate the classic style of the home.

Cottage in Upperville

Cozy Country Getaway in the Heart of Upperville

Located in the center of the historic village of Upperville - across from the Hunter's Head Tavern. House is situated on 2.5 acres of beautiful gardens. It feels like an English cottage that dates back to early 1900s and is newly updated. Tall ceilings with tons of light make this house feel very spacious. There are 2 large bedrooms with 3 beds. Upstairs is a large loft with desk area. Parking provides space for 5 vehicles. Dogs are welcome! Wifi available.

4.96 out of 5 average rating, 145 reviews

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

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 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.