Guesthouse holiday rentals in Jefferson County

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Top-rated Guesthouses in Jefferson County

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Top Guest favourite

Guesthouse in Round Hill Village

4.96 out of 5 average rating, 47 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 favourite

Guesthouse in Charles Town

4.77 out of 5 average rating, 124 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.

Top Guest favourite

Guesthouse in Purcellville

4.98 out of 5 average rating, 248 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 favourite

Guesthouse in Harpers Ferry

4.84 out of 5 average rating, 19 reviews

Rustic Walkout Cabin Basement

Rustic Walkout Basement Cabin in Historic Harpers Ferry Enjoy the charm of a cozy cabin with a private entrance and parking for one car. This one-level space has no steps to navigate, except for a 4-inch step to the bathroom. The front door opening is 35 inches wide. Features wood-paneled walls, an electric fireplace, and modern amenities. Perfect for hikers, history lovers, and pet owners. Walk to monuments, trails, and local dining. Experience Harpers Ferry’s beauty with comfort and style.

Guest favourite

Guesthouse in Harpers Ferry

5 out of 5 average rating, 25 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 favourite

Guesthouse in Harpers Ferry

4.88 out of 5 average rating, 33 reviews

Hidden Creek Retreat

Relax and find peace in this newly renovated sanctuary. Take a break in the spacious, calm atmosphere and let go of your worries. Take a quick hike through the backyard and into the woods! Follow the creek down through the woods to the scenic Shenandoah River! Service animals are welcome with a $150 fee per 3-day stay, plus $50 per night after. Pets are not allowed. A $500 fine applies if a pet is brought in. Emotional support animals are considered pets and are not allowed at anytime.

Guest favourite

Guesthouse in Purcellville

4.86 out of 5 average rating, 66 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!

Guesthouse in Harpers Ferry

4.9 out of 5 average rating, 10 reviews

Spacious living w/ Mountain view

Relax with the whole family at this peaceful place to stay. . Enjoy the scenes and sounds of nature surrounding this 4 acre retreat. with Full Kitchen, outdoor grill and fire pit. within a few minutes to Appalachian trail, walking distance to Shenandoah River. Hiking, biking, rafting, wineries & breweries nearby. 10-minutes to Harper's Ferry, Maryland Heights Trail, Antietam Battlefield, Shepherdstown, WV. Downtown Frederick 30 minutes. Baltimore and Washington D.C. 1-1.5 hour drive.

Guest favourite

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 favourite

Guesthouse in Harpers Ferry

5 out of 5 average rating, 40 reviews

Between the Rivers Guest House

Between the Rivers Guest house is centrally located in historic Harpers Ferry and walking distance to all shops and restaurants. You will enjoy staying in the towns original "Telephone Building". Take in river views from our front porch and a relaxing outside patio. Walk to the Appalachian trail, go white water rafting, check out a local winery, and tour the vast history that our town has to offer. We look forwarding to having you as our guest!

Superhost

Guesthouse in Harpers Ferry

4.87 out of 5 average rating, 60 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 favourite

Guesthouse in Purcellville

4.97 out of 5 average rating, 125 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.