Guest house holiday rentals in Shenandoah Valley

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Top-rated guest house rentals in Shenandoah Valley

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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.
Guest house in Hinton
4.96 out of 5 average rating, 766 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
The recently renovated stone cottage features rustic charm with a modern metal roof. Large windows invite natural light, and the outdoor patio area is equipped with seating and an umbrella for shade, surrounded by greenery and trees.
Guest house in Middleburg
5 out of 5 average rating, 121 reviews

18th Century Middleburg Cottage

This recently renovated 2-story 18th Century stone cottage is the perfect blend of rustic and luxury, featuring stone walls, exposed beams, wood floors, a stone patio and outdoor fireplace, as well as Mountain views. Property includes kitchen, bathroom, and a living space with wood stove and dining table. Upper floor features bedroom and additional reading room. Cottage is just minutes from historic Middleburg in the heart of horse and wine country, perfect for relaxing or recharging getaways.

Top guest favourite
A wooden staircase leads to the entrance of a renovated carriage house nestled among trees. The exterior features warm wood siding and a charming front door, framed by greenery that enhances the inviting atmosphere of the space.
Guest house in Harrisonburg
4.97 out of 5 average rating, 162 reviews

Hideaway Studio on Ashtree Lane

This renovated historic carriage house is 2 blocks from Harrisonburg’s vibrant downtown. The space is light and airy with gabled ceilings and sky-lights that open. It is located on a leafy residential back-alley, with private entrance and off-street parking. JMU’s bluestone campus is a 10 minute walk away. We’ve set-up this space for a range of guests: from JMU parents visiting their children to people traveling for business who are seeking a more textured experience with home comforts.

Top guest favourite
A cozy interior space features a comfortable sofa and a spacious bed adorned with a quilt. A dining area with four chairs is visible, along with a wooden cabinet and a mounted television. Natural light streams in through the windows, complemented by warm wooden accents.
Guest house in McGaheysville
4.97 out of 5 average rating, 357 reviews

Peaceful Oak Cottage

This peaceful cottage has a rustic, yet modern feel to it. It is set on the edge of a wooded area with plenty of wildlife to enjoy, near Massanutten Resort. Enjoy the ambiance of the small electric fireplace, well-equipped kitchenette and dining area, or the front porch swing. The bathroom features an old-fashioned claw foot tub, fitted with a shower head. Enjoy a complimentary bottle of sparkling cider and a basket of snacks with your stay. We look forward to extending our hospitality to you.

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.
Guest house in Sperryville
4.99 out of 5 average rating, 127 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
A charming cottage is framed by lush greenery, with a covered porch extending across the front. Colorful flowering bushes add vibrancy to the landscape, which features well-maintained garden beds and a birdbath. The cottage is situated on a grassy area that leads to a secluded wooded backdrop.
Guest house in Syria
4.96 out of 5 average rating, 420 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.

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.
Guest house in Smithsburg
4.97 out of 5 average rating, 825 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.

Top guest favourite
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.
Guest house in Massies Mill
4.99 out of 5 average rating, 105 reviews

Solar-powered Guesthouse at Peak Time Property

This cozy guesthouse is a perfect getaway. It has SPECTACULAR views of the Priest and Three Ridges. Located in Massies Mill, it is a 20-30 minute drive to the Appalachian Trail, Wintergreen, breweries, wineries, and distilleries. It is also practically around the corner from Pharsalia Events. There are several convenience stores close by, but the closest grocery store is an 18 minute drive. Situated on 26 acres, there is more than a mile of marked trails available to walk as you wish.

Top guest favourite
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.
Guest house in Mount Crawford
4.96 out of 5 average rating, 188 reviews

Country Cabin near JMU/ Skyline Dr / Massanutten

Welcome to your very own country cabin getaway! As soon as you enter our property and take in the views we promise you will feel the stress of travel melt away. You will enjoy the scenic views of the Blue Ridge Mountains while being conveniently located minutes from shopping, JMU and all that Harrisonburg, VA has to offer. We are: 10 min to JMU Campus 10 min to Downtown Harrisonburg 15 min to Massanutten Four Season Resort 25 min to Shenandoah National Park (Swift Run Gap Entrance)

Top guest favourite
The exterior view of the cottage features a walkway leading to a white door, flanked by climbing roses and hanging flower pots. A small outdoor table and chairs are set on the gravel, inviting guests to enjoy the pleasant surroundings.
Guest house in New Market
4.98 out of 5 average rating, 484 reviews

Stay in a piece of history! Private Entire Cottage

Built in 1797, this cottage sits next to the historic William Rupp House, and is #17 on the self-guided walking tour! Although you are staying in a piece of history, you still get the privacy you need to comfortably explore all Shenandoah Valley has to offer. 19.6 miles away from JMU, 5.2 miles away from Endless Caverns, right off Interstate 81, and within walking distance of local stores, coffee shops, and restaurants... buckle in for a load of fun with this convenient location.

Top 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.
Guest house in Boston
4.99 out of 5 average rating, 229 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.

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.
Guest house in Flint Hill
4.97 out of 5 average rating, 156 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.

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