Guesthouse vacation rentals in Staunton

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Top-rated guesthouse rentals in Staunton

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Guest favorite

Guesthouse in Charlottesville

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)

Guest favorite

Guesthouse in Orange

5 out of 5 average rating, 232 reviews

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.

Guest favorite

Guesthouse in Lexington

4.95 out of 5 average rating, 261 reviews

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!

Guest favorite

Guesthouse in Gordonsville

4.91 out of 5 average rating, 181 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.

Guest favorite

Guesthouse in Lexington

5 out of 5 average rating, 246 reviews

Spectacular Mountain views

Enjoy the breathtaking scenery when you stay in this beautiful, brand new space. A transformed outbuilding has become a quaint guest cottage with all of the amenities of home. Full kitchen w/all cooking essentials, K-cup coffee machine, new appliances, granite counter tops, full bath w/private shower and a jacuzzi tub with mountain views. Wake up in your master bedroom to spectacular mountain views. Living room w/electric fireplace, large screen TV. Your own private deck/pergola/gas grill.

Guest favorite

Guesthouse in Syria

4.96 out of 5 average rating, 368 reviews

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.

Guest favorite

Guesthouse in Schuyler

4.91 out of 5 average rating, 377 reviews

Homestead at HeartRock

Welcome to HeartRock Homestead. Our sweet spot offers rustic charm and modern comfort. Come for a private grownup nature camp! A getaway for couples, friends and families. Really, there is something for everyone. AND we have great check in and check out times to maximize your stay! Have you ever heard the whippoorwill sing while watching the stars or grazed organic cut flowers amongst the morning dew or felt a seasoned sunset kiss your heart? We hope to see you soon!

Guest favorite

Guesthouse in Fort Valley

4.92 out of 5 average rating, 196 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.

Guest favorite

Guesthouse in Charlottesville

4.92 out of 5 average rating, 131 reviews

Cavalier Carriage House Suite | Near UVA

Small yet mighty. This carriage house is the perfect retreat for UVA games, special events, and those exploring Charlottesville. Conveniently located within walking distance to Scott Stadium, and a short distance to UVA, Downtown Charlottesville, and 5th Street Station Shopping Center. Hosts have 2 small, friendly dogs (Mac and Pippie) in the main house which may be seen in the patio entrance area. Guests have access to patio and grill.

Guest favorite

Guesthouse in Flint Hill

4.96 out of 5 average rating, 113 reviews

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.

Guest favorite

Guesthouse in Front Royal

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.

Guest favorite

Guesthouse in Madison

4.97 out of 5 average rating, 245 reviews

Hebron Valley Cottage

Nestled in the scenic Hebron Valley, this 2 bedroom 1 bath cottage is the perfect getaway from busy, city life. The cottage offers panoramic views of the Blue Ridge Mountains, including Old Rag and is located near several wineries, breweries, restaurants, antique shops, hiking trails and historic sites. The cottage is 3 miles from the town of Madison and is convenient to Charlottesville, Culpeper and Orange.

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Staunton guesthouse rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

Guest favorite

Guesthouse in Charlottesville

4.91 out of 5 average rating, 146 reviews

The Cottage at Eastwood Farm and Winery

Guest favorite

Guesthouse in Crozet

4.86 out of 5 average rating, 298 reviews

Stylish Carriage House Suite near Crozet center

Guest favorite

Guesthouse in Charlottesville

4.91 out of 5 average rating, 568 reviews

Downtown studio, walk to corner/downtown mall/UVA

Guesthouse in North Downtown

4.75 out of 5 average rating, 116 reviews

Historic Cottage in Downtown Charlottesville

Guest favorite

Guesthouse in Boston

4.98 out of 5 average rating, 177 reviews

The Bunkhouse- simple & serene w/mountain views

Guest favorite

Guesthouse in Charlottesville

5 out of 5 average rating, 119 reviews

Hidden Gem near town and Monticello with a pool

Guest favorite

Guesthouse in Charlottesville

4.91 out of 5 average rating, 431 reviews

Hardpan Cottage

Superhost

Guesthouse in Charlottesville

4.84 out of 5 average rating, 43 reviews

Luxury 2BR Suite One Mile From UVa, Near Downtown

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Guest house rentals with a patio

Guest favorite

Guesthouse in Massies Mill

4.99 out of 5 average rating, 73 reviews

Solar-powered Guesthouse at Peak Time Property

Guest favorite

Guesthouse in Mount Crawford

4.96 out of 5 average rating, 143 reviews

Country Cabin near JMU/ Skyline Dr / Massanutten

Guest favorite

Guesthouse in Troy

4.99 out of 5 average rating, 161 reviews

Beaver Pond Farm - Near Charlottesville

Guest favorite

Guesthouse in Barboursville

4.98 out of 5 average rating, 42 reviews

Burnley Cottage

Guest favorite

Guesthouse in Staunton

4.98 out of 5 average rating, 42 reviews

Peaceful rural retreat with pool and spa

Superhost

Guesthouse in Keswick

5 out of 5 average rating, 4 reviews

3 Cottages on luxurious Keswick estate with pool

Guest favorite

Guesthouse in Rapidan

4.98 out of 5 average rating, 47 reviews

Romantic & Private Guest Cottage on a Lovely Farm

Guest favorite

Guesthouse in Woodstock

4.97 out of 5 average rating, 119 reviews

Cozy cottage nestled on 8 acres with mountain view

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Guest house rentals with a washer and dryer

Guest favorite

Guesthouse in Charlottesville

5 out of 5 average rating, 152 reviews

Luxury tiny house 3 min from UVA

Guest favorite

Guesthouse in Harrisonburg

4.95 out of 5 average rating, 74 reviews

Swanky and Modern Downtown Guesthouse

Guest favorite

Guesthouse in Afton

4.92 out of 5 average rating, 555 reviews

Tiny House Bliss on Brew Ridge Trail. Wintergreen

Guest favorite

Guesthouse in Charlottesville

4.98 out of 5 average rating, 140 reviews

Delightful loft cottage in the heart of CVille

Guest favorite

Guesthouse in Charlottesville

4.98 out of 5 average rating, 46 reviews

Stony Point Cottage

Guest favorite

Guesthouse in Lexington

4.92 out of 5 average rating, 93 reviews

Guest House in the Valley

Guest favorite

Guesthouse in Earlysville

4.98 out of 5 average rating, 340 reviews

Cottage at Frog Jump- woodland privacy at its best

Guest favorite

Guesthouse in Cartersville

5 out of 5 average rating, 15 reviews

The Bright Spot Guest House

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Quick stats about guesthouse rentals in Staunton

Total rentals
10 properties
Nightly prices starting at
G$16,719 GYD before taxes and fees
Total number of reviews
1.1K reviews
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Local attractions
Frontier Culture Museum, Gypsy Hill Park, and Walmart Supercenter

Guesthouse vacation rentals in Staunton

Top-rated guesthouse rentals in Staunton

Vacation rentals for every style

Houses

Apartments

Cabins

Popular amenities for Staunton guesthouse rentals

Family-friendly guest house rentals

Guesthouse in Charlottesville

Guesthouse in Crozet

Guesthouse in Charlottesville

Guesthouse in North Downtown

Guesthouse in Boston

Guesthouse in Charlottesville

Guesthouse in Charlottesville

Guesthouse in Charlottesville

Guest house rentals with a patio

Guesthouse in Massies Mill

Guesthouse in Mount Crawford

Guesthouse in Troy

Guesthouse in Barboursville

Guesthouse in Staunton

Guesthouse in Keswick

Guesthouse in Rapidan

Guesthouse in Woodstock

Guest house rentals with a washer and dryer

Guesthouse in Charlottesville

Guesthouse in Harrisonburg

Guesthouse in Afton

Guesthouse in Charlottesville

Guesthouse in Charlottesville

Guesthouse in Lexington

Guesthouse in Earlysville

Guesthouse in Cartersville

Quick stats about guesthouse rentals in Staunton

Total rentals

Nightly prices starting at

Total number of reviews

Wifi availability

Popular amenities

Local attractions

Destinations to explore