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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Guest favorite

Guesthouse in Purcellville

4.99 out of 5 average rating, 209 reviews

The Cottage at Dunthorpe Farm

The cottage is a fully restored wagon barn sitting on a 48 acre 1790's farm nestled against the Blue Ridge Mountains. You'll enjoy quality, comfort and pastoral views. We are a fully licensed and inspected B&B. The cottage is stocked with organic cereal, juice, coffee and tea. Each morning you are treated to a continental breakfast of fresh pastry and fruit sourced from local farms. We are close to Harpers Ferry, WV, Leesburg, VA and Middleburg, VA, and are just a 30 minute drive from Dulles.

Nov 12 – 19

G$49,330 GYD per night

Guest favorite

Guesthouse in Stephens City

5.0 out of 5 average rating, 6 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 and gas fireplace w/ access to independent gym 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

Nov 25 – Dec 2

G$42,871 GYD per night

Guest favorite

Guesthouse in Lovettsville

4.94 out of 5 average rating, 122 reviews

The Patent House

Built around 1760, our log cabin sits on our 3 acre farmette, in the countryside in view of the foothills that separate VA, WV & MD. It's fully renovated, with a master bedroom (queen), full bath & convertible sofa downstairs (full). The cabin is next door to our house & shares a fence with our pasture where our miniature donkeys live. We have yappy dogs and friendly outdoor cats. we're in the country, so bugs do make their appearance, but they tend to go straight to the window sills.

Apr 24 – May 1

G$28,062 GYD per night

Guest favorite

Guesthouse in Purcellville

4.83 out of 5 average rating, 24 reviews

Garden Cottage

Enjoy this quaint Garden Cottage in the backyard of the 1793 Stone House & experience the tiny town of Hillsboro. Perfect for a couple’s getaway to enjoy Virginia wine country or if you’re coming for a wedding or other event. It’s 5 miles from the Appalachian Trail that’s great for any day-hikers or a nice break for thru-hikers. Like a hotel room, but much better with your own private space & lovely back porch to relax & enjoy the many flowers in the backyard. You won’t want to leave!

Oct 1 – 8

G$26,187 GYD per night

Guest favorite

Guesthouse in Keedysville

4.98 out of 5 average rating, 191 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

Jul 10 – 17

G$26,316 GYD per night

Guest favorite

Guesthouse in Bluemont

5.0 out of 5 average rating, 56 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!

Jun 8 – 15

G$57,940 GYD per night

Guest favorite

Guesthouse in Hamilton

4.98 out of 5 average rating, 116 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.

Oct 5 – 12

G$58,721 GYD per night

Superhost

Guesthouse in Purcellville

4.8 out of 5 average rating, 256 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).

Aug 23 – 30

G$14,394 GYD per night

Guest favorite

Guesthouse in Warrenton

4.98 out of 5 average rating, 256 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.

Jul 10 – 17

G$30,490 GYD per night

Guest favorite

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!

Aug 13 – 20

G$49,811 GYD per night

Guest favorite

Guesthouse in Front Royal

4.88 out of 5 average rating, 253 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.

Jan 24 – 31

G$41,746 GYD per night

Guest favorite

Guesthouse in Bluemont

4.99 out of 5 average rating, 310 reviews

Skyhorse Retreat Guest House

In the middle of VA wine country and only minutes to three Appalachian Trail trailheads. Located 45 miles west of Washington D.C., on a 10-acre property on top of the Blue Ridge Mountains. Private guesthouse (built Jan 2020) with a large deck overlooking trees. The Guest House sleeps 4, has a full kitchen, and access to a Hot Tub at the main house. Breakfast items and snacks included.

Jun 16 – 23

G$30,532 GYD per night