Guesthouse holiday rentals in Shenandoah Valley

Find and book unique guesthouse rentals on Airbnb

Top-rated Guesthouses in Shenandoah Valley

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Top Guest favourite
A charming guest house is nestled among lush green trees, showcasing a steeply pitched roof and large windows. A wooden staircase leads up to the entrance, which features a small deck surrounded by vibrant foliage.
Guesthouse in Hinton
4.97 out of 5 average rating, 774 reviews

StreamSide Guesthouse in Mountains/National Forest

Stream-side guest house with charming views in lovely mountain setting; just steps from trailhead into GW National Forest. Peaceful, private and all to yourself, this 720 sq ft loft is a stylish, comfy retreat. During the day go hiking, wading, or just relax on the deck overlooking the stream. At night let sounds of rushing water and the gentle voices of nature lull you to sleep. Only 11 miles to Harrisonburg. Fast wifi with Prime/Netflix. A meditative retreat from which to explore the valley.

Top Guest favourite
A cozy living area features wooden paneling and a stone fireplace with an active flame. Two deer heads are mounted on the wall. A television is positioned above the fireplace, and small evergreen trees add a touch of nature to the space.
Guesthouse in Fairhope
4.97 out of 5 average rating, 203 reviews

Mountain View Acres Getaway

Enjoy nature in a beautiful peaceful setting with 100 acres of privately owned property. Breathtaking panoramic views spanning 45 miles in a tranquil natural spot with hiking trails throughout. Handicap accessible. Within a short drive of 2 major ski resorts, the Flight 93 Memorial and 2 wineries. Several restaurants and a brewery also within a 15 minute drive. The property includes an outside firepit that is a favorite place for guests to relax and enjoy the breathtaking views of the mountains.

Top Guest favourite
Guesthouse in Charlottesville
5 out of 5 average rating, 140 reviews

Historic HomeTract Cottage UVA/Charlottesville/Ivy

Hometract Cottage is a historic one bedroom home (NRHP, circa 1800) centrally located 15 minutes or less from Charlottesville, UVA, Crozet, Monticello, wineries and more. The cottage features ensuite bath, fully stocked kitchen, living/workspace with comfortable sleeper sofa, mature landscaping for privacy, and covered front porch. Hometract is a quiet 3-acre property with terraced garden views. Visit our chicken coop, relax in the hammock, or walk to the garden shop or Duner's restaurant.

Top Guest favourite
The guest house is framed by lush greenery and softly illuminated by hanging lights that create a welcoming ambiance. A spacious porch with potted plants invites relaxation, while the multi-gabled roof and cupola add character to the charming exterior. Gravel pathways lead to the entrance.
Guesthouse in Sperryville
4.99 out of 5 average rating, 135 reviews

Countryside getaway 5 min. from Old Rag parking!

Just 5 min away from Old Rag trailhead in Shenandoah National Park and merely minutes from wineries/breweries. Our guest house is close to White Oak Canyon, Skyline Drive, Three Blacksmiths, Washington, and Luray Caverns! Book here if you like: -Escaping the hustle and bustle, and relaxing in nature -Hearing birds sing while sipping coffee/tea/wine on the porch -Observing wildlife (including our chickens and bees) -Fishing on the Hughes River in our backyard -Stargazing and spotting fireflies

Top Guest favourite
The exterior of the guesthouse is showcased, featuring a deck with outdoor seating and an umbrella. Tall windows allow for natural light, complementing the green siding. Lush landscaping surrounds the house, creating a natural, inviting setting.
Guesthouse in Smithsburg
4.97 out of 5 average rating, 839 reviews

Jewel Vinsota Artist's Guesthouse

Less than a mile from the Appalachian Trail, the dog-friendly Jewel Vinsota Artist's Guesthouse is the perfect get-away to explore nature or your artistic leanings. The house is full of original artwork, hand-crafted details, and books on art and architecture. Wander the grounds and find sculpture, ponds, and trails through the woods. Want to hike the entire 40-mile length of Maryland on the Appalachian Trail? Start and end at the Jewel Vinsota and we can drop you off and pick you up.

Guest favourite
A spacious hot tub is surrounded by a stone patio, offering views of the lush green landscape. Nearby, two outdoor chairs are positioned for relaxation, while a grill is situated in the corner. The soothing water reflects the cloudy sky above.
Guesthouse in Fort Valley
4.92 out of 5 average rating, 291 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 favourite
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
4.97 out of 5 average rating, 234 reviews

The Skyhouse- simple & serene w/mountain views

Enjoy the solace and beauty of the Blue Ridge Mountains with modern and local comforts. Retreat and explore on this old 100acre farm- via foot- or float on the tiny pond in a kayak or SUP. Or venture out to Shenandoah National Park, the local coffee shops, eateries, wineries, and breweries. Whatever you choose the skyhouse is stocked with roasted coffee, farm-fresh eggs, fresh-baked bread, teas and soaps from our incredible local homesteaders and artisans.

Guest favourite
Guesthouse in Harrisonburg
4.96 out of 5 average rating, 114 reviews

Spacious Historic Studio | Downtown | 65in TV

Discover downtown Harrisonburg from this unique, renovated 1800s Carriage House studio. Perfect for 2-3 guests, this bright space features a king bed, kitchenette, and a 65" Smart TV. Enjoy a private entrance and free parking, just a 5-minute walk from Main Street's dining, breweries, and JMU's campus. Your ideal base for city exploration or a cozy retreat. *This unit is pet-friendly, but you MUST have your furry friend listed on your reservation*

Top Guest favourite
The guesthouse's exterior features sturdy stone walls and a green metal roof. White window shutters enhance the classic design. A covered porch provides a welcoming entrance, while lush green grass and neatly trimmed hedges surround the building. Scenic views of the property are visible in the background.
Guesthouse in Flint Hill
4.97 out of 5 average rating, 163 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.

Top Guest favourite
A small, rustic cabin is set amidst a lush green landscape, framed by trees. The cabin features a front porch with a green door and a chimney, surrounded by a well-maintained grassy area. Natural light filters through the foliage, creating a serene atmosphere.
Guesthouse in Syria
4.88 out of 5 average rating, 711 reviews

Cozy 1 room cabin in the mountains.

In the heart of the Shenandoah mountains. 1 mile from White Oak Canyon and Old Rag for amazing hikes. Perfect for the fly fisherman (lots of local streams) or a nice quiet get-away for a couple. Once you park your car you can sit back and just listen to the river flowing in the back yard & enjoy a nice beverage next to the fire pit. The property is a very special place! UPDATE: New kitchen counters and new table and chairs

Guest favourite
A two-story house with a wood-shingled exterior and a covered porch features a welcoming entrance. Steps lead up to a spacious deck surrounded by greenery, providing a warm outdoor space for relaxation.
Guesthouse in Morgantown
4.95 out of 5 average rating, 518 reviews

Trillium Acres Guest House

Located 10 miles from downtown Morgantown and the stadium. Cooper's Rock is just 12 miles away, with hiking, mountain biking and rock climbing. Our cozy house with modern amenities can accommodate 6 people with 2 queen beds, 1 twin and a queen pull-out sofa. Trillium Acres Cottage and Trillium Acres Hilltop are next door and a short walk through the woods for larger groups needing more space.

Guest favourite
The exterior of the guest house displays a rustic wooden facade, featuring stone accents and a large arched window. Two outdoor light fixtures are positioned on either side of the entrance, enhancing the inviting appearance of the structure amidst lush greenery.
Guesthouse in Harrisonburg
4.9 out of 5 average rating, 119 reviews

Hall Guest House- Hot Tub- Sauna

Spend a relaxing weekend in the comforts of the Hall Guest House. Nestled against the Massanutten Mountains, this cozy retreat is perfect for a quiet get-away alone or with your favorite person. The guest house offers a private entrance, luxury queen bed, full bathroom, sauna, outdoor hot tub, and bar area with grill and half bath. The main house is occupied by the property owner and family.

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