Guesthouse vacation rentals in Clarke County

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Top-rated guesthouse rentals in Clarke County

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Top guest favorite

A picturesque outdoor patio features a stone fire pit surrounded by several Adirondack chairs. Lush greenery provides a backdrop, with views of open fields in the distance. A small table is positioned nearby, contributing to a relaxed outdoor environment.

Guesthouse in Purcellville

4.98 out of 5 average rating, 238 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.

Top guest favorite

A wooden deck captures a serene sunset view over expansive green fields and distant mountains. A glass sits on the table, reflecting the warm hues of the evening sky, while scattered trees complement the landscape.

Guesthouse in Stephens City

5 out of 5 average rating, 17 reviews

Ventura Cottage: 360-views/HotTub/4 acres/Gym

Breathtaking 360d views/Outdoor Tub/4 acres/Gym/<10min to Winchester Ideal for a couple, an independent guesthouse adjacent to the main house on 4-acre lot, completed in 2021. Full kitchen & gas fireplace w/access to gym & hot tub on the premises. Mountain and valley views all-round, front porch offers breathtaking sunset views while back porch features hot tub with 270 degree vistas of orchards, mountains, trees. * 3-bedroom/4 bath main house also available for rent, see Ventura Manor

Guest favorite

A newly renovated kitchen features a central wooden island with a rustic design. Light-colored cabinets contrast with the warm tiled floor. Large windows invite natural light, providing views of the surrounding trees. A staircase with wooden railings enhances the space's inviting feel.

Guesthouse in Round Hill Village

5 out of 5 average rating, 12 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

Guesthouse in Keedysville

4.98 out of 5 average rating, 209 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

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

4.95 out of 5 average rating, 221 reviews

Cottage Escape in Virginia Wine Country

Welcome to LoeLynn Farms! ✔ Peaceful two-story cottage on 25 private acres ✔ Located in Virginia’s Wine Country, 75 minutes from D.C. ✔ Enjoy a private lake, outdoor living spaces, and a fully equipped kitchen ✔ Close to wineries, breweries, restaurants, and historic neighborhoods ✔ Ideal for a romantic getaway or a serene retreat • Note: The main home is roughly 60 meters from the Guest House, so you may hear our kiddos from time to time playing! We can't wait to host you!

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

5 out of 5 average rating, 87 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, 147 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.

Guest favorite

A large window frames a serene view of rolling green hills and a tranquil pond. Fenced pastures can be seen in the distance, creating a calming rural landscape under a gently clouded sky.

Guesthouse in Purcellville

4.81 out of 5 average rating, 273 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 - no satellite, TV, or Internet. 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

Two wooden Adirondack chairs are positioned around a small table on a grassy area, framed by trees. A rolling landscape is visible in the background, featuring green fields and dotted with tree lines and a fence.

Guesthouse in Warrenton

4.97 out of 5 average rating, 315 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

Guesthouse in Lovettsville

4.99 out of 5 average rating, 130 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!