Guesthouse vacation rentals in Clarke County

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Top-rated guesthouse rentals in Clarke County

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Top guest favorite

The exterior of the studio loft features a red wooden facade with white trim and a steeply pitched roof. Two French doors provide entry, flanked by wooden steps leading to a broad landing. An air conditioning unit is visible on the left side.

Guesthouse in Round Hill Village

4.96 out of 5 average rating, 46 reviews

Wine Country Loft

Located in the heart of Loudoun Wine Country. Large, peaceful yard in downtown Round Hill, walking distance to a diner and shops. A perfect location for biking, hiking and outdoor enthusiasts. Our friendly dog, Maddie, or cat, Chase, may greet you upon arrival. This studio loft above our carriage house includes one queen bed and a deluxe queen fold out couch.Full kitchen and bath, large projector screen entertainment center, private porch and patio with fire pit.Perfect for families or a couple.

Top guest favorite

A dining nook features a wooden table with three matching chairs, positioned between two large windows. The windows overlook a green landscape, providing ample natural light. A small decorative piece rests on the table, complementing the warm wooden tones of the flooring.

Guesthouse in Leesburg

4.99 out of 5 average rating, 105 reviews

Private 2 BR, 1 Bath Carriage House Near Wineries!

Fox Farm Carriage Apartment is a private country retreat, located on 10 acres, on a quiet, private road. It has 2 bedrooms, one bath, with incredible views (the sunsets are amazing) and filled with natural light. It has a private entrance w/ staircase to 2nd floor. The bath has a luxury shower and dual vanities. It has a full kitchen stocked with cookware, Direct TV, and large family room. Very close to Leesburg and local wineries and breweries. Linens and towels, soaps, shampoos are included.

Guest favorite

The interior of the cabin features natural wood paneling and high ceilings, creating an open and spacious atmosphere. A full-sized bed is dressed in soft linens, complemented by a decorative rug on the polished wooden floor. Light filters in through two windows, enhancing the serene space.

Guesthouse in Front Royal

4.87 out of 5 average rating, 107 reviews

Cozy Shenandoah River Cabin (10min to Nat’l Park!)

Come get away to our cozy guest cabin, just 10 mins from Shenandoah National Park and a 5 min walk to the Shenandoah River! Perfect for a peaceful stay in a gorgeous natural setting. High ceilings, open concept, wood panelling and a private enclosed patio. Close to vineyards, breweries and outdoor attractions. (Please note, there isn't a full kitchen) If you have more than 3 guests, please let us know. We have a second cabin on the property that we can offer as an additional space.

Guest favorite

A serene countryside view showcases a spacious green lawn bordered by trees and hills in the background. Two houses are visible: one with a wraparound porch and the other a smaller structure. An organic garden is seen in the foreground, framed by a simple fence.

Guesthouse in Keedysville

4.97 out of 5 average rating, 223 reviews

City Dog Farm

Comfortable, light-filled one bedroom apartment on 10 acres in Maryland near Antietam battlefield and Harpers Ferry, WV. We have chickens, an organic garden, hills, woods and a stream. Apartment is 15 minutes from Harpers Ferry, Antietam battlefield, the C&O canal, river rafting on the Potomac or Shenandoah, vineyards, the Appalachian trail and small towns including Boonsboro and Shepherdstown, WV. 30 minutes to Frederick or Hagerstown/1.5 hours to DC or Baltimore. SORRY NO PETS

Guest favorite

Two chairs are positioned near a campfire ring on a grassy area, surrounded by trees. A gently sloping hill leads down to a pond, with a wooden fence visible in the distance. Sunlight filters through the leaves, creating a shaded and inviting space.

Guesthouse in Purcellville

4.81 out of 5 average rating, 277 reviews

Barn Apartment in VA Wine Country

Barn apartment in the upper level of a bank barn. Fourteen miles from downtown Leesburg, 5 miles from Harper's Ferry, 1 mile from VA-9 Appalachian trail head. Close to Harper's Ferry Adventure Center, wineries, breweries, tubing, kayaking, hiking, farms. Full kitchen. Unplugged with the exception of Wi-Fi - no satellite or TV. There is cell signal. Rate includes 6% Virginia state tax and 7% Loudoun County hotel tax. 1 queen bed, 1 twin, and 1 floor mattress (pull out futon).

Top guest favorite

The charming exterior of the guest house is showcased, featuring a manicured garden with colorful flowers. A small dining set is positioned by the entrance, complemented by a grill nearby. Large windows reflect natural light, inviting views of the surrounding landscape.

Guesthouse in Bluemont

4.99 out of 5 average rating, 104 reviews

Bluemont Escape:Walk to Bears Den; Bear Chase Brew

Charming guest house that is part of a larger estate home property. Walk to Bear’s Den and the Appalachian Hiking Trails as well as popular Bear Chase Brewery. Short drive to wineries, breweries, restaurants, and river. Bluemont escape is located in historic Loudoun County and includes a kitchenette and huge bedroom. This apartment sits on five acres with two other units. Enjoy the sunset from Bear’s Den overlook just across the street, grill out, or enjoy fire pit!

Top guest favorite

The timber-framed chalet is surrounded by vibrant flower gardens, showcasing various colorful blooms. Large windows and a balcony enhance the exterior, framed by trees creating a natural backdrop. A patio area with seating is visible in the foreground, inviting guests to enjoy the peaceful surroundings.

Guesthouse in Hamilton

4.99 out of 5 average rating, 153 reviews

Trailside Chalet (A storybook chalet with hot tub)

The Trailside Chalet is situated on the W and OD Trail, halfway between Leesburg and Purcellville, Va - an ideal base location for visiting wineries, breweries, and the pastoral countryside of Loudoun County. The chalet will put you just steps from the trail for walking/cycling/horseback riding. Relax and enjoy the amenities of one-of-a-kind interior including wood burning fireplace and peaceful surroundings with hot tub. A perfect getaway for a couple or family.

Top guest favorite

The Alton Cottage showcases a quaint exterior featuring a wooden deck and stone steps leading up to the entrance. Surrounded by green grass and trees, the weathered stone chimney from the original structure is partially visible, adding a historic touch to the peaceful landscape.

Guesthouse in Warrenton

4.97 out of 5 average rating, 334 reviews

The Alton Cottage -a luxury country retreat

The Alton Cottage is a charming, newly refurbished 1820s guest house- formerly a summer kitchen to the original farm house. Views are of rolling fields and their bovine occupants. We are within 30 minutes of almost 20 wineries and another 20 breweries, 5 min to Airlie, and only 5 mi to Old Town Warrenton. We are also close to several antique stores, farmers markets and Shenandoah National Park. We strive to make every guests stay special.

Top guest favorite

A spacious bedroom features exposed wooden beams and rustic log walls. A plush white bed is centered in the room, flanked by two bedside tables with lamps. A wooden wardrobe and an armchair are positioned by the window, enhancing the cozy atmosphere.

Guesthouse in Waterford

4.92 out of 5 average rating, 125 reviews

Cabin On The Creekside

Cabin on the Creekside is a log cabin located on beautiful wooded property just outside of Waterford, VA. The cabin is a perfect spot to unwind, relax, and come explore Loudoun County which is filled with wineries, breweries, farm to table restaurants, hiking trails and more! Beautifully decorated space, king size bed, large comfy couch, 75 inch TV, and kitchenette are a few highlights of the space. Looking forward to your stay!

Top guest favorite

The exterior of a cozy brick building is framed by lush greenery and trees. A small patio area features two chairs, surrounded by freshly mulched beds with low shrubs. The building's porch is screened, offering a welcoming entrance.

Guesthouse in Front Royal

4.89 out of 5 average rating, 265 reviews

"Cabbin" at Mountain Home B&B

The "Cabbin" of historic Mountain Home is cozy, comfortable space, 120 yards east of the Appalachian Trail, on Route 522 (Remount Road), 3 miles from Front Royal, VA. 6 beds, a bathroom, small kitchen and dining area. Reserve the whole "Cabbin" here. See "Mt. Home Cabbin" listings to reserve a floor. No TV in Cabbin, but we have WiFi. Dogs are welcome, but not other types of pets. Meals taxes are included in the listing price.

Top guest favorite

The bright bedroom features a spacious bed with crisp white linens and a light gray throw. A comfortable armchair is positioned beside a side table, with natural light flooding in through large windows framed by light gray walls.

Guesthouse in Lovettsville

4.99 out of 5 average rating, 147 reviews

Modern dreamy mountain view oasis in wine country

Right in the heart of Loudoun County's wine, beer and equestrian country. If you are looking for an outdoor getaway with access to the Ap Trail, biking, kayaking, etc., here for the wine and beer or simply for a change of scenery, this is the place for you. Watch the sun go down right from your bed or, "The Meadow" with the Blue Ridge Mountains as your backdrop. Slowly sip coffee or tea from the hammock, it's up to you. Book now!

Top guest favorite

The exterior of the cottage features a classic white facade with black shutters and a large star ornament above the entrance. Well-maintained landscaping includes small shrubs and a stone walkway leading to the door, set against a backdrop of open green fields and trees.

Guesthouse in Lovettsville

4.96 out of 5 average rating, 239 reviews

Cottage Escape in Virginia Wine Country

Tucked among rolling hills, this cozy cottage rests on 25 acres with a private lake just beyond your door. Sip wine beneath the stars, paddle at sunrise, or wander where the wildflowers grow. Just minutes from vineyards, brews, and historic charm, it's a perfect escape to slow down and reconnect. You may hear the laughter of our little ones nearby—just part of the magic here at the farm. We can't wait to welcome you.