Guest house holiday rentals in Clarke County

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Top-rated guest house rentals in Clarke County

Guests agree: these guest house rentals are highly rated for location, cleanliness and more.

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Guest favourite
Illuminated lanterns are hung from decorative hooks among trees, casting a warm glow. The surrounding area is decorated with blooming daffodils in vibrant yellow, set against lush greenery, contributing to a peaceful outdoor setting as dusk approaches.
Guest house in Charles Town
4.77 out of 5 average rating, 126 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.

An outdoor deck features a round table surrounded by several chairs. A shaded umbrella provides coverage over the table, while soft lighting from string lights enhances the ambiance. In the background, a storage shed is visible, alongside a well-maintained lawn.
Private room in Winchester
4.83 out of 5 average rating, 6 reviews

Welcome to a Perfect Night Stay!

Step into my humble abode, where comfort and warmth embrace you like an old friend. Nestled in a serene and quiet neighborhood, this cozy retreat promises an unforgettable experience. My place carries a gentle hum of tranquility and you'll enjoy a home away from home experience, as every detail whispers hospitality. Whether you're here for leisure, work, or simply to escape, your perfect night awaits. Feel free to make yourself at home, and let the magic of this Airbnb rental envelop you.

Top guest favourite
A charming exterior view of the recently renovated house showcases its distinctive blue wooden siding and pitched roof. Lush flower beds filled with yellow and white blooms surround the entryway, while the well-maintained garden adds vibrant color to the setting.
Guest house in Berryville
5 out of 5 average rating, 13 reviews

1800s Cozy Kitchen House

This award winning whimsical 1800s kitchen house that served the main house is walking distance to all town businesses and great for history and art lovers. Located on historic South Church Street, the property backs to Rose Hill Park, The Barns of Rose Hill music/art venue and the town government center/ library. Everything was chosen piece by piece with respect to the structure’s history with the addition of modern conveniences. Original narrow steps may be difficult for some guests.

Top guest favourite
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.
Guest house in Bluemont
4.99 out of 5 average rating, 111 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!

Guest favourite
A stone patio offers two wooden chairs and a central fire pit, providing a setting to enjoy views of the Shenandoah River and surrounding nature. Leafless trees frame the landscape with distant hills visible under a clear blue sky.
Private room in Charles Town
4.91 out of 5 average rating, 32 reviews

Thistle Room - Coorie Inn LITE - TWO (2)

Bedroom walls are partially soundproofed to encourage a restful, quiet stay. Keypad lock on the bedroom door for your safety. Access to kitchenette and living space including a pool table, air hockey table, and seating to enjoy the beauty of nature from the comfort of an airconditioned space. Shared bathroom with large walk-in shower! On-site parking. A short walk down a gravel hill to the keypad entry door. Stone patio overlooking the Shenandoah River!

Superhost
A stone patio features two wooden chairs arranged around a fire pit. The space overlooks the Shenandoah River, framed by bare trees. A clear sky with scattered clouds enhances the serene natural landscape.
Private room in Charles Town
4.53 out of 5 average rating, 17 reviews

Sage Room - Coorie Inn LITE

Corrie Inn LITE is a paired down version of Corrie Inn. Corrie Inn LITE has a private bedroom, all other spaces have the potential to be shared. Perched just over the Shenandoah River (private river access) 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!

A living area is presented with a teal sofa and floral armchair. A glass-top coffee table is centered on a patterned area rug. Two lamps with white bases provide warm lighting, complemented by framed wall art featuring floral designs. A round mirror enhances the space.
Guest house in Upperville
4.77 out of 5 average rating, 44 reviews

Christmas in Middleburg

Perfect for the Middleburg Christmas Parade and holiday outings! Stay on a beautiful farm just minutes from downtown Middleburg, wineries, and festive events. This private top-floor garage apartment offers mountain and horse-farm views, a full kitchen, a spacious living room, a master with a king bed + two daybeds, and a second bedroom with two twins. Enjoy peaceful sunsets after a magical holiday day in town.

Top guest favourite
A hot tub is situated on a deck surrounded by trees, with sunlight filtering through the branches. A pink float is placed beside the tub. The calming water reflects the warm light, creating a serene atmosphere.
Guest house in Bluemont
4.99 out of 5 average rating, 380 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.

Guest favourite
The guest cabin bedroom features a spacious bed topped with layered bedding and decorative pillows. Wooden accents surround the area, including a bench at the foot of the bed. A large mirror and potted plants add character, while natural light filters through the windows.
Guest house in Bluemont
4.95 out of 5 average rating, 163 reviews

Blueridge Mountain Guest Cabin- Amongst the Trees

Cozy guest cabin on the Blue Ridge Mountain Range. Enjoy the peaceful atmosphere, nature, clean air, and access to several nearby hiking trails, the Shenandoah river, numerous wineries and breweries, wedding venues, and quant towns. This place is truly a peaceful retreat from the "grind".

A welcoming slate sign displays the text 'Welcome to the Little Acorn Cottage' in a handwritten style. Soft greenery is visible in the foreground, enhancing the inviting setting of the entrance.
Guest house in Bluemont
5 out of 5 average rating, 5 reviews

Little Acorn Cottage

Kick back and relax in this calm, professionally designed space. The Little Acorn Cottage was completely renovated in 2025! Steps from historic Twin Oaks Tavern Winery est. 1892 and the Appalachian Trail!

Popular amenities for guest house rentals in Clarke County