Guesthouse vacation rentals in Shenandoah Valley

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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, 743 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.

Guest favourite
Guesthouse in Shenandoah
4.93 out of 5 average rating, 136 reviews

Guesthouse with Massage Chair & GAME ROOM

Come and enjoy this newly remodeled, quiet and centrally-located guest house in the heart of beautiful Shenandoah. About 15 minutes from Massanutten resort, and Shenandoah National Park. Walking distance to multiple restaurants including Italian and Mexican, Big Gem park, and Dollar General, and Fuel stations nearby. Outside you have access to common amenities including the game room building, hot tub and sauna building, two fire pit areas, a spaceball gyro ride, tennis rackets, and corn hole.

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, 156 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.

Guest favourite
An interior view showcases a cozy living space with wooden walls and ceiling, abundant natural light from large windows, and a ceiling fan. A gray sofa is complemented by a colorful throw blanket, while a small dining area with bright chairs is positioned nearby.
Guesthouse in Afton
4.92 out of 5 average rating, 613 reviews

Spacious Tiny Home Close to Wine, Beer & Mountains

A six-figure tiny home in the epicenter of VA's Brew Ridge Trail. FORBES listed this model as the most beautiful tiny house in the world. "Big Tiny", built in 2017, is a luxurious retreat that is huge on both character and amenities. This handcrafted home boasts a full-sized kitchen private bedroom, cozy sleeping loft, 2 large screen TVs, and full bath with tub. With a cathedral ceiling and walls of windows, this Escape Traveler XL is the flagship offering of the premiere tiny home builder.

Top guest favourite
A charming cottage is nestled among mature trees and vibrant landscaping, featuring a welcoming entrance. The rustic structure is complemented by lush greenery and seasonal foliage, emphasizing a serene, natural setting.
Guesthouse in Earlysville
4.98 out of 5 average rating, 377 reviews

Cottage at Frog Jump- woodland privacy at its best

Guesthouse ideal for two people. Small cottage (1 bed, 1 bath) is situated in a country setting on ten wooded acres along a large serene pond. It features a darling kitchenette with sink, fridge, microwave and toaster/convection oven. (No stove top, no oven.) You'll enjoy birdsong and views of various wildlife. A quiet, restful place to stay when you want to be near Shenandoah Nat’l Park, UVA, Charlottesville, Virginia wineries, Monticello, Montpelier, CHO, and other close-by attractions.

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.
Guesthouse in Mount Crawford
4.96 out of 5 average rating, 168 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.
Guesthouse in New Market
4.98 out of 5 average rating, 413 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.
Guesthouse in Boston
4.99 out of 5 average rating, 208 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 Alton Cottage showcases a quaint exterior featuring a wooden deck and stone steps leading up to the entrance. Surrounded by green grass and trees, the weathered stone chimney from the original structure is partially visible, adding a historic touch to the peaceful landscape.
Guesthouse in Warrenton
4.97 out of 5 average rating, 338 reviews

The Alton Cottage -a luxury country retreat

The Alton Cottage is a charming, newly refurbished 1820s guest house- formerly a summer kitchen to the original farm house. Views are of rolling fields and their bovine occupants. We are within 30 minutes of almost 20 wineries and another 20 breweries, 5 min to Airlie, and only 5 mi to Old Town Warrenton. We are also close to several antique stores, farmers markets and Shenandoah National Park. We strive to make every guests stay special.

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, 146 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 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
4.87 out of 5 average rating, 682 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 charming, two-story structure with a green metal roof is visible. The building features classic design elements and a gravel driveway, where a dark car is parked. Lush greenery surrounds the property, with distant mountains hinting at the natural landscape.
Guesthouse in Elkton
4.97 out of 5 average rating, 194 reviews

Carriage House private, 10 min to Shen. Nat'l Park

Private, well-appointed studio apartment. On same small farm property as main house, but separated with private entrance. Queen bed. View of the Massanutten Mountain range, grazing sheep, and beautiful sunsets. Centrally located just outside Elkton--15 minutes to Shenandoah National Park; 5 minutes to Massanutten Resort. Local restaurants, coffee shop, brewery, and town parks nearby. No smoking or pets.

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