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 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.

Oct 5 – 12

G$49,396 GYD per night

Guest favorite

Guesthouse in Round Hill

5.0 out of 5 average rating, 7 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.

Jun 30 – Jul 7

G$31,812 GYD per night

Guesthouse in Berryville

4.67 out of 5 average rating, 6 reviews

The Rutherford B. Hayes Guest House

A 6-7-bedroom, 6-bath guest house nestled in a secluded, wooded lot within the Historic Rosemont Manor estate grounds. The multiple bed bedrooms and foldout couch sleep up to 18. Guest rooms are named after officers who fought in the Battle of Berryville on the grounds. The house has a living room, kitchen, and Fijitsu heating/cooling inverters. A dining table in the kitchen seats up to 8. The house has a front porch with swing. A picnic table, outside grill and brick fire ring are available.

May 23 – 30

G$146,313 GYD per night

Guesthouse in Charles Town

4.74 out of 5 average rating, 100 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.

Jun 20 – 27

G$37,668 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!

Nov 8 – 15

G$26,324 GYD per night

Guest favorite

Guesthouse in Knoxville

4.94 out of 5 average rating, 204 reviews

Tiny House at Tiny Hidden Ridge

This 109sqft tiny house is cute, cozy, and the ultimate tiny house experience. If you've been wanting to check out tiny living, this is the place. It's not for everyone so read on to find out if it's for you. Small entrance door, wall ladder to the sleeping loft, compost toilet and small shower. Perfect for one or two people looking for a quiet getaway to read, write or enjoy the outdoors. The ladder weight limit is 200 lbs per person. Not recommended for children.

Jul 20 – 27

G$20,283 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).

Jun 8 – 15

G$14,466 GYD per night

Guest favorite

Guesthouse in Harpers Ferry

4.91 out of 5 average rating, 11 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!

Nov 3 – 10

G$22,216 GYD per night

Guesthouse in Purcellville

The Wee Bairn Suite: Glamping Get-Away

This idyllic tiny studio is 10 x 18'. Perfect for hikers or vineyard guests needing a safe and comfortable stay. The kitchen and full bath is in the main house, a quick walk from the Studio. There is a portable sink and toilet in the studio, small refrigerator, and basic ammenities. This historic property is a perfect mountainview get-away.

Oct 5 – 12

G$18,760 GYD per night

Guest favorite

Guesthouse in Purcellville

4.97 out of 5 average rating, 91 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.

Sep 19 – 26

G$34,541 GYD per night

Superhost

Guesthouse in Harpers Ferry

4.93 out of 5 average rating, 15 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!

Nov 14 – 21

G$19,090 GYD per night

Guesthouse in Purcellville

The Peripatetic Place

Located in the heart of Purcellville, Virginia. You’ll find yourself immersed with unique shops, restaurants and endless activities. All nestled in a safe family friendly community. Encompassed by 30+ award-winning wineries, a bike trail that goes to Washington DC. Community centers, parks, playgrounds, hiking trails and much more.

Dec 23 – 30

G$34,573 GYD per night