Guesthouse vacation rentals in Clarke County

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Top-rated guesthouse rentals in Clarke County

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

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Top guest favorite

A fire pit is centrally placed on a stone patio, showcasing bright flames dancing atop the wood inside. Flanking the fire pit are two blue Adirondack chairs, inviting relaxation. In the background, a red barn-like structure adds a rustic touch to the serene setting.

Guesthouse in Round Hill Village

4.98 out of 5 average rating, 42 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 charming red barn with white trim is surrounded by lush greenery and well-maintained landscaping. A gravel path leads to the entrance, framed by neatly arranged stones and bushes. The building features large windows that invite natural light into the interior.

Guesthouse in Purcellville

4.98 out of 5 average rating, 241 reviews

The Cottage at Dunthorpe Farm

The Cottage is a restored wagon barn nestled against the Blue Ridge Mountains. You'll enjoy quality, comfort, quietude, and pastoral views. We are a fully licensed and inspected B&B on a 1790's farm in rural Loudoun County VA. Each morning you are treated to a continental breakfast of fresh pastry, fruit sourced from local farms, and homemade jams which we quietly deliver by 7:30 unless otherwise requested. Note that the base price is for 1-2 people. Guests 3 and 4 have additional fees.

Guest favorite

A compact black device is positioned on a light-colored countertop near a window. The device displays signal strength indicators on a small screen. A wall outlet is visible in the background with a charging unit connected.

Guesthouse in Round Hill Village

5 out of 5 average rating, 13 reviews

The Cottage

Super private on a farm, newly renovated private 2-bedroom, 2-bathroom guest house surrounded by trees. Updated with new kitchen, baths (full bath on main), freshly painted. Enjoy the serene ambiance on the front porch or gather around the fire pit, stone patio for cozy evenings under the stars, fenced backyard. Abundance of wildlife and birds to enjoy nature and stars. 5 minutes to Rt. 7, 10 minutes to Purcellville, many wineries, venues nearby. Discount for longer stays is firm.

Guest favorite

An owl is perched on a branch amidst dense green foliage. Its distinctive feather pattern and large, round eyes are visible, blending with the natural surroundings. Soft sunlight filters through the leaves, creating a serene atmosphere in the wooded area.

Guesthouse in Keedysville

4.98 out of 5 average rating, 213 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

A serene landscape features expansive grassy fields surrounded by trees. A small pond reflects the morning light, and a gravel path leads through the area. Fencing outlines a section of the land, suggesting pastures or vineyards beyond.

Guesthouse in Purcellville

4.81 out of 5 average rating, 275 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).

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, 96 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 chalet is nestled among snow-covered trees, softly illuminated by string lights along the roof eaves. Pathway lights lead to a patio area with table seating, enhancing the serene winter landscape.

Guesthouse in Hamilton

4.99 out of 5 average rating, 151 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

A rustic exterior of Alton Cottage is framed by leafless trees, with a stone foundation and wooden steps leading up to the entrance. Rolling green fields extend into the distance, illuminated by warm sunlight, creating a serene rural landscape.

Guesthouse in Warrenton

4.97 out of 5 average rating, 326 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.

Superhost

The living area presents warm wooden beams and floors, complemented by natural light from multiple windows. A spacious white bed is positioned in the corner, while a large comfortable couch and decorative elements enhance the inviting nature of the cabin.

Guesthouse in Waterford

4.92 out of 5 average rating, 121 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!

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, 261 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

A clean, white letterhead displaying the name 'The Meadow' at the top. The paper is placed on a smooth wooden desk alongside a decorative mirror and some scattered blank sheets, creating a serene workspace atmosphere.

Guesthouse in Lovettsville

4.99 out of 5 average rating, 136 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!

Guest favorite

A cozy coffee nook features a Keurig coffee maker on a marble countertop. A wire basket filled with coffee pods and a wall-mounted board with notes are visible, alongside jars with assorted items. Natural light streams in through a nearby window, revealing a lush green landscape outside.

Guesthouse in Lovettsville

4.96 out of 5 average rating, 228 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.