Guesthouse vacation rentals in Jefferson County

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Top-rated guesthouse rentals in Jefferson County

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Guest favorite

Guesthouse in Round Hill

4.97 out of 5 average rating, 29 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.

Guest favorite

Guesthouse in Charles Town

4.75 out of 5 average rating, 113 reviews

Coorie Inn

We are growing. Private bedroom added to make this a two full bedroom offering with kitchenette. Please come stay a spell! Perched just over the Shenandoah River (river access in multiple places) with mountain views, this getaway lets you get lost in nature with all the creature comforts of home. ***Dogs are welcome with PRIOR approval from the host. Please message me if you'd like to bring your fur bud! ***Please see additional info for all of the comforts provided! ***No smoking please.

Guest favorite

Guesthouse in Purcellville

4.99 out of 5 average rating, 231 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.

Superhost

Guesthouse in Harpers Ferry

5 out of 5 average rating, 6 reviews

Riverview Suite at La Soledad

Kick back and relax, surrounded by incredible views and sounds of nature! This brand new space has tons of windows and light, overlooking the Potomac river. Use your private entrance to go out and picnic in the lavender field, or sit by the firepit and enjoy the sounds of the Potomac! Or relax with a book on the huge window seat! Only a mile from the National Historical Park, it is an easy walk to the shops, restaurants and trails. After a long hike, a brand new king size bed awaits you

Guest favorite

Guesthouse in Purcellville

4.86 out of 5 average rating, 43 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!

Guest favorite

Guesthouse in Purcellville

4.81 out of 5 average rating, 266 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).

Guest favorite

Guesthouse in Harpers Ferry

4.93 out of 5 average rating, 41 reviews

River Chase Cottage

Nestled on a 9-acre historic farmstead on the Banks of the Potomac, our fully restored cottage offers an idyllic getaway for adventurous couples. Indulge in a refined, bucolic sojourn in Harpers Ferry, with sufficient distance to give you the feeling of total disconnection, yet conveniently close to town should you require anything. Your adventure awaits at the River Chase Cottage. Book now for an unforgettable stay!

Guest favorite

Guesthouse in Purcellville

4.96 out of 5 average rating, 110 reviews

The Carriage House: Pathway to a Romantic Getaway

Forget your worries in this spacious and serene space. The Carriage House is located down a tree-lined driveway situated on a peaceful 3.5 acres. A keyless private entrance reveals a very open and spacious floor plan with six large windows letting in an abundance of natural light surrounded by splendid manicured lawns and wooded views.

Superhost

Private room in Harpers Ferry

4.69 out of 5 average rating, 39 reviews

River View East - Full Bed

Located 60 miles from Washington DC in the middle of the Harpers Ferry Historic District just steps from the C&O and Appalachian Trails, the Potomac & Shenandoah Rivers, shops, the Inn offers a restaurant & shop open daily 6 a.m.-10 p.m. & 8 guest rooms,Only 3 pet friendly. A place for all seasons for many reasons!

Guest favorite

Private room in Harpers Ferry

4.8 out of 5 average rating, 64 reviews

Room In Central Historic Downtown - Shenandoah

Guest favorite

Guesthouse in Summit Point

4.97 out of 5 average rating, 29 reviews

The Cottage at Ruby Summit Point

The Cottage at Ruby Summit Point - Your Home at the Track. Comfy 2 bedroom cottage in Summit Point - minutes from Summit Point Motorsports Park! We welcome visitors to the track or just to explore the beautiful local area around Harpers Ferry/Shepherdstown or south into Virginia wine/horse country.