Guesthouse vacation rentals in Staunton

4.98 out of 5 average rating, 101 reviews

Guesthouse in Broadway

Katie's Shenandoah Kottage

The guest cottage is "attached" to the back side of the 1880's farm house and shares an acre of land. The property is located In the heart of the Shenandoah Valley, in the small town of Broadway. It is just a short drive from all the valley has to offer: hiking, Civil War battlefields, wineries, breweries, cavern tours, skiing, golfing, Shenandoah National Park, James Madison University, antique shopping, and Mennonite markets. You must be 25 or older to rent. There is a two night minimum stay.

A light-filled seating area features a comfortable gray sofa adorned with an orange accent pillow. Potted plants are positioned nearby, enhancing the natural ambiance. Large windows allow ample sunlight and offer views of the outdoor greenery, while a modern floor lamp provides additional lighting.

5 out of 5 average rating, 105 reviews

Honey House-modern loft near UVA/Monticello

Modern loft style 800sqft guesthouse. Lots of light and privacy in a quiet neighborhood, just 7-10 minutes to Scott Stadium/UVA/restaurants/downtown mall and Thomas Jefferson’s Monticello. Central to many wineries/breweries. You are in nature but close to everything Charlottesville. With a comfortable Queen size bed, and sleeping cot available if necessary. It is clean, comfortable and spacious. A great place to unwind for a good night’s sleep and sweet dreams. (discount apply to weekly/monthly)

5 out of 5 average rating, 244 reviews

The guesthouse features a charming façade with a red roof and white trim. A pathway leads from the driveway to the entrance, bordered by well-maintained gardens. Lush greenery surrounds the property, creating a tranquil atmosphere. The balcony is visible, inviting relaxation.

Guesthouse in Orange

Taj Garage Guesthouse

Newly constructed (2021) above garage guesthouse with private, self check-in entrance, off-street parking, located among historic homes just 4 blocks to restaurants, shops, park and art galleries in downtown Orange. Guesthouse includes a fully equipped kitchen, queen bed, full bath, seating area, TV, wifi and balcony. Handcrafted heart pine furniture. Level 2 EV Charger. Kitchen includes refrig, stove, microwave, toaster and Keurig. Close to superb wineries, breweries and historic sites.

4.96 out of 5 average rating, 277 reviews

Guesthouse in Lexington

Entire Country Cottage guesthouse / Very Private

Gloriously private without feeling secluded, this charming guesthouse was totally updated in 2019. Enjoy the peace and quiet. Go for a walk or bike ride on the 28 plus acres or pretty rural lanes. 2.5 miles away is Lake Robertson for activities . Sit on the porch too! On a snowy night, enjoy the wd-burning fireplace . (We will often leave fireplace prepared to light. Gas heating also). Get cozy with the full kitchen, washer/dryer, games and books. DirecTv in the living room and bedroom. too!

Guesthouse in Gordonsville

The exterior of La Petite Maison showcases a charming guest house with a large screened porch, surrounded by vibrant flower beds. A turquoise umbrella shades a lounge chair next to the seasonal in-ground pool, providing a relaxing outdoor space.

4.91 out of 5 average rating, 182 reviews

La Petite Maison at Hedgeapple Hollow

La Petite Maison (our guest house) is the perfect place to simply get away from the hustle and bustle and relax! Sit in the private screen porch and watch the sun melt into the mountains. Deer, hummingbirds, bluebirds, and the occasional turkey like to hang out on the 8 acres of the property, perfect for any wildlife lover. Enjoy the fenced in common area featuring a seasonal in-ground pool. Conveniently situated near award-winning wineries, Montpelier, and historic downtown Gordonsville.

4.96 out of 5 average rating, 380 reviews

A tranquil sitting area is positioned beside a gently flowing stream, surrounded by lush greenery. Two black chairs rest on a gravel surface, with natural rocks and trees providing a serene backdrop. Sunlight filters through the leaves, creating a calm and peaceful atmosphere.

Guesthouse in Syria

Little House on Strother Run

Nestled between Mount Tom and Double Top Mountain and at the edge of the Shenandoah National Forest, Little House is the perfect starting out and ending point for a peaceful and relaxing stay in the Appalachian Mountains. Little House is located at the edge of our 7 acre property. You'll enjoy the bucolic atmosphere of our farmette which includes use of our shared sitting area on Strother Run. The sitting area is shared with the main house which is rented or used by our family periodically.

4.94 out of 5 average rating, 108 reviews

A spacious deck features red and white Adirondack chairs positioned towards a scenic view of rolling hills and a sunset. The horizon is illuminated with warm colors, while a green landscape stretches out, providing an inviting backdrop for relaxation.

Guesthouse in Lexington

Guest House in the Valley

Our guest house is only a few minutes away from Historic Lexington. The house has one master bedroom with a king size bed. We have a fully functional kitchen, washer and dryer, and full bathroom. We are also close to the Appalachian Trail, the Blue Ridge Parkway, the Virginia Military Institute, Washington and Lee University, and the Virginia Horse Center. The house provides great views and a place to relax either on the back porch, the front deck, or a walk through the surrounding area.

Guesthouse in Fort Valley

A covered deck area features a circular stone fire table surrounded by four comfortable wicker chairs with plush cushions. Umbrellas provide shade, and a grassy area with trees can be seen in the background, creating a serene outdoor space.

4.93 out of 5 average rating, 214 reviews

Romantic Mountain Getaway⛰ hot tub*king bed*sauna

This newly renovated guesthouse is the perfect place to relax and refresh. This 10 acre property is nestled in the heart of the Shenandoah Valley!! Close to hiking, wineries, the river! Soak in the hot tub overlooking the mountains, relax in the dry sauna, take in the nature as you paddle on the private pond or lounge on the dock. Rest well in the new memory foam king bed. This is the perfect place to return after a day of exploring or simply spend the day relaxing.

4.85 out of 5 average rating, 246 reviews

A spacious studio suite features a queen-size bed and comfortable seating area with two chairs. A butcher block bar is positioned near the entrance, alongside a small waste bin. The bathroom is partially visible with a bright shower curtain, and a television is mounted on the wall.

Guesthouse in Maurertown

Studio along i81: Near Wine, Beer, Hiking & Nature

Newly renovated detached studio guest-suite located in the beautiful Shenandoah County with country feels and easy access to I81. It features a butcher block bar for eating/working, a queen size bed, tv with Netflix along with Chromecast so you can cast your favorite shows from your phone/laptop, and during the summer you'll have the quietest and smart ac unit on the market. It has a shared driveway with the host's primary residence.

4.96 out of 5 average rating, 124 reviews

A historic stone guesthouse stands prominently on a 115-acre farm. Its two-story structure features green roofs and an inviting front porch, framed by lush grass and trees. A wooden fence encloses the property, enhancing the serene rural landscape.

Guesthouse in Flint Hill

Summer kitchen guesthouse at Caledonia Farm 1812

Summer kitchen guesthouse built of stone in 1812 and located on a 115 acre free-range cattle farm on the National Register of Historic Places. The first floor is a living room with the original cooking fireplace and a kitchenette. Upstairs is a loft bedroom and bath. Housekeeping is provided on Monday and Friday mornings. Enjoy the peace and quiet, dark skies, scenic views, adventure, and culinary excellence of Rappahannock County.

Guesthouse in Front Royal

The exterior of a cozy brick building is framed by lush greenery and trees. A small patio area features two chairs, surrounded by freshly mulched beds with low shrubs. The building's porch is screened, offering a welcoming entrance.

4.89 out of 5 average rating, 261 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.

4.97 out of 5 average rating, 121 reviews

The cottage is set in a wooded area, elevated on a wraparound deck surrounded by mature trees. Natural light is filtered through the leaves, creating dappled patterns on the ground. The exterior features a muted color palette complemented by a charming brick chimney.

Guesthouse in Keswick

Gladstone Cottage

Charming, private 1 bedroom cottage oasis in the heart of Keswick horse country, estates and vineyards, yet only 18 minutes to UVA. Very secluded and peaceful setting. Nestled in woods but full of light. Large bay window looks out on a walk-through perennial garden. From the deck, enjoy watching horses graze in the adjacent pasture.

Vacation rentals for every style

Get the amount of space that is right for you

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Popular amenities for Staunton guesthouse rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

A charming brick cottage features a sloped metal roof and white-trimmed front door, framed by vibrant greenery and flowering bushes. A grassy area leads to the entrance, creating a welcoming exterior. Soft clouds drift above, adding to the serene outdoor setting.

4.91 out of 5 average rating, 147 reviews

The Cottage at Eastwood Farm and Winery

4.86 out of 5 average rating, 308 reviews

A bright living area features a cozy sofa adorned with decorative pillows. A vibrant piece of wall art adds color, while a rustic sliding barn door leads to another room. A wooden bar with metal stools offers a casual dining space.

Guesthouse in Crozet

Stylish Carriage House Suite near Crozet center

4.91 out of 5 average rating, 583 reviews

Downtown studio, walk to corner/downtown mall/UVA

4.98 out of 5 average rating, 189 reviews

A modern studio space features large windows that allow natural light to fill the room. A cozy yellow chair sits beside a small coffee table, with a guitar resting on a stand nearby. The bed area is visible in the background, framed by a stylish shelf.

Guesthouse in Boston

The Bunkhouse- simple & serene w/mountain views

A serene landscape showcases expansive green fields, framed by rolling hills and colorful autumn foliage. Majestic mountains rise in the distance under a clear blue sky, creating a peaceful and inviting natural setting.

5 out of 5 average rating, 123 reviews

Hidden Gem near town and Monticello with a pool

A spacious living area features a light-colored sofa and a wooden coffee table. Bright lighting illuminates the room, which opens to a modern kitchen with bar seating. A large mirror with a colorful frame enhances the sense of space, while plush carpet adds comfort.

4.84 out of 5 average rating, 44 reviews

Luxury 2BR Suite One Mile From UVa, Near Downtown

Guesthouse in Ruckersville

The guesthouse exterior features a rustic wooden façade with a shingled roof. A spacious deck enhances the entryway, adorned with potted plants and grass arrangements. An umbrella stands in a seating area, providing shade for outdoor relaxation, amid a backdrop of trees.

4.98 out of 5 average rating, 280 reviews

Mountain Guesthouse*Hot Tub*WiFi*Firepit*Grill*SNP

4.91 out of 5 average rating, 387 reviews

A covered porch area features a comfortable seating arrangement adorned with a yellow throw blanket, surrounded by greenery. Natural stone landscaping and wooden elements provide a warm, rustic charm, inviting relaxation in a serene outdoor setting.

Guesthouse in Schuyler

Homestead at HeartRock

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Guest house rentals with a patio

Guesthouse in Massies Mill

Lush green grass stretches across the foreground, leading to a scenic vista dominated by rolling hills and misty mountains. The trees display varying shades of green, indicating the freshness of spring, with a backdrop of soft clouds partially covering the peaks.

4.99 out of 5 average rating, 77 reviews

Solar-powered Guesthouse at Peak Time Property

Guesthouse in Mount Crawford

A welcoming living area features a large area rug with floral patterns. Two couches provide comfortable seating, and a flat-screen TV is mounted on the wall. The open layout allows views into the kitchen and dining space, enhancing the connection between areas.

4.96 out of 5 average rating, 152 reviews

Country Cabin near JMU/ Skyline Dr / Massanutten

4.99 out of 5 average rating, 170 reviews

An aerial view captures a spacious guest house nestled among trees displaying vibrant autumn foliage. The surrounding landscape features a mix of green and colorful leaves, with an open area visible beside the property. Outdoor amenities are discernible, blending harmoniously with the natural setting.

Guesthouse in Troy

Beaver Pond Farm - Near Charlottesville

The exterior of a light blue house is showcased, featuring a spacious deck with seating and a grill. A landscaped garden with small plants borders the yard, while green hills and trees are visible in the background under a partly cloudy sky.

4.98 out of 5 average rating, 53 reviews

Stony Point Cottage

Guesthouse in Gordonsville

A charming white house is framed by a vibrant tree with red foliage, set against a clear blue sky. A gravel path leads toward the home, which features a black roof and a welcoming front porch, surrounded by well-maintained grass and shrubs.

5 out of 5 average rating, 26 reviews

Guest House at Annandale

Guesthouse in Barboursville

An open kitchen features a spacious wooden island with black bar stools. Modern appliances are visible, along with open shelving displaying kitchenware. Light grey walls provide a neutral backdrop, while a doorway leads to adjacent areas, enhancing the layout's flow.

4.98 out of 5 average rating, 52 reviews

Burnley Cottage

4.98 out of 5 average rating, 48 reviews

A welcoming kitchen space is displayed with vibrant yellow walls. Stainless steel appliances include a refrigerator and an oven with a hood. A wooden dining table is set with placemats, and natural light filters through the window above the sink.

Guesthouse in Staunton

Peaceful rural retreat with pool and spa

5 out of 5 average rating, 4 reviews

Guesthouse in Keswick

3 Cottages on luxurious Keswick estate with pool

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Guest house rentals with a washer and dryer

The exterior of La Casita features a modern design with smooth gray siding and large windows. A manicured green lawn surrounds the home, with blooming trees providing shade. A small patio area with chairs is visible, inviting outdoor relaxation.

5 out of 5 average rating, 166 reviews

Luxury tiny house 3 min from UVA

Guesthouse in Harrisonburg

A corridor links the bathroom and living area, featuring a glass shower and a dual sink vanity with dark cabinetry. A stylish futon is positioned in the living space, with natural light coming from a nearby window. The floor is adorned with wooden planks.

4.93 out of 5 average rating, 83 reviews

Swanky and Modern Downtown Guesthouse

4.92 out of 5 average rating, 572 reviews

Guesthouse in Afton

Elegant Tiny Home Close to Wine, Beer & Mountains

The exterior of the guest house features a clean, modern design with large windows that allow natural light to fill the interior. A well-maintained grassy area surrounds the structure, complemented by lush greenery and a small covered entryway.

4.98 out of 5 average rating, 145 reviews

Delightful loft cottage in the heart of CVille

4.96 out of 5 average rating, 71 reviews

A serene pond scene is illuminated by a water fountain, creating reflections on its surface. Surrounding trees provide a natural frame, while soft lighting enhances the peaceful atmosphere. A blue paddle boat is visible along the shoreline, contributing to the tranquil setting.

Guesthouse in Shenandoah

Guesthouse with Massage Chair & GAME ROOM

4.97 out of 5 average rating, 68 reviews

Guesthouse in Cumberland

Lucid Dreams little house

4.9 out of 5 average rating, 39 reviews

Double doors open to reveal a covered patio space overlooking lush greenery and distant mountain views. A welcoming mat lies at the entrance, enhancing the connection between indoor and outdoor living.

Guesthouse in Middletown

Riverfront Oasis with Mountain Views, Near Town