Vacation rentals in Sperryville

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Top-rated vacation rentals in Sperryville

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Top guest favorite

The exterior of the tiny house is shown, featuring a light-colored siding and several windows that allow natural light inside. A wooden deck with steps leads to the entrance, and a fenced area provides privacy. Lush greenery surrounds the home, adding a natural backdrop.

Tiny home in Culpeper

4.98 out of 5 average rating, 120 reviews

3 Bed Tiny House in Culpeper w/ Kitchen & Firepit!

Welcome to our cozy tiny house in Culpeper, VA! This is the perfect retreat for couples/small groups looking for a unique & memorable experience. W/ open 2 lofts & a pull out couch this home sleeps up to 6 guests. The fully equipped kitchen allows for easy cooking. The composting toilet is an eco-friendly alternative w/o giving up convenience. Enjoy the outdoor fire pit & lounge area or visit some of the nearby attractions like Shenandoah National Park, shops downtown, & Death Ridge Brewery!

Top guest favorite

A spacious common area features a red couch and an antique-style chair, complemented by a wooden dining table with four chairs. Skylights introduce natural light, while two ceiling fans provide air circulation. A television is positioned across from the seating area, enhancing relaxation.

Guesthouse in Flint Hill

4.97 out of 5 average rating, 179 reviews

Three Meadows Farm, outdoor views, great location

As you approach the driveway on the private lane, you'll be welcomed by beautiful meadows and rolling hills. Set on 10 acres in a shaded, forest of mature trees it's comfortable year round. There are beautiful mountain views from several locations on the property. It's peaceful and quiet here most of the time. We're conveniently located just minutes from Flint Hill, not much farther to Washington VA, Sperryville and Front Royal. It's a two bedroom/one bathroom apartment above a detached garage.

Guest favorite

A geodesic dome structure is situated on a wooden deck, surrounded by lush trees. An outdoor dining table with umbrella and seating is visible, alongside a hot tub. Soft lights adorn the deck, creating a warm and inviting ambiance amidst the natural setting.

Dome in Luray

4.93 out of 5 average rating, 100 reviews

Dream Dome - Romantic Retreat + Wifi A/C + Hot Tub

Welcome to the Dream Dome! Our newly constructed geodesic dome is the perfect romantic getaway in the beautiful Shenandoah Valley. Enjoy all the amenities of home (wifi, A/C, kitchen, bathroom) all while being fully immersed in nature and a short 8 min drive to the National Park! The home includes a King bed, a 2nd level loft with a queen bed, 1 large bathroom, a dining area, full stocked kitchen, and an outdoor patio area with hot tub, outdoor dining table, and fire pit. Come dream with us!

Guest favorite

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.

Guesthouse in Syria

4.96 out of 5 average rating, 396 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 favorite

A two-story farmhouse sits surrounded by lush greenery, with mountains visible in the background. The front porch is accented with two chairs. The white exterior contrasts with the vibrant surroundings, providing a welcoming appearance to guests approaching the entrance.

Home in Sperryville

4.98 out of 5 average rating, 106 reviews

Walk to Old Rag/Shenandoah*Hot tub* dogs welcome

Make some memories at this unique and family and dog-friendly place. Relax in the hot tub after hiking Old Rag. This rustic redone farmhouse with modern amenities is a short walk to the trailhead for the hike up Old Rag, a short walk to Hughes River fishing, and a short drive to Sperryville, historic Madison, wineries, breweries and other Shenandoah National Park hikes. The house is surrounded by acres of fenced open space, with a front porch, deck, weber gas grill, and 360 Mountain Views.

Guest favorite

A rustic cabin is illuminated by warm golden light from its windows, set against a soft twilight sky. The log exterior reflects the vintage charm of the structure, while the surrounding trees create a serene atmosphere, inviting guests to relax on the front porch.

Place to stay in Bentonville

4.99 out of 5 average rating, 482 reviews

John Pope Cabin Browntown Va. We now have Starlink

Our cabin, located in the foothills of the Appalachian Mountains is uniquely positioned overlooking a large open field where hawks hunt and bears leisurely stroll. Our neighbors have horses that peer over the fence (nosy) pet them but don’t feed them, please. Our cabin was built in 1865 by a Confederate soldier returning from the Civil War. Eleven children were born and raised in John Pope Cabin. Our cabin is rustic. An inviting front porch with swing is waiting for you @walnuthillcabin

Guest favorite

The image shows a quaint cottage with a small porch overlooking a serene landscape. A gentle stream flows alongside the property, surrounded by lush greenery and trees. The sky is bright with fluffy clouds, adding to the tranquil outdoor setting.

Farm stay in Sperryville

4.91 out of 5 average rating, 159 reviews

Carriage House @ Sharp Rock Winery at Old Rag Mtn

Join us at Sharp Rock Vineyards in our 1850 Carriage House, a cozy romantic one room cottage perfect for a couple, set above a rushing trout stream at the base of Old Rag Mountain. Enjoy the peace of a private setting only minutes from Shenandoah National Park and hiking at Old Rag and White Oak Canyon. We are 10 minutes from Sperryville and close to local wineries, breweries, and eateries. In the evening enjoy our riverside fire pit or the brilliant firefly display on summer nights.

Top guest favorite

The yurt is set against a starry night sky, surrounded by towering trees. A spacious deck leads to the yurt's entry, while warm light emanates from its windows. The scene showcases a natural ambiance highlighted by foliage and a gravel path leading to the entrance.

Yurt in Etlan

4.96 out of 5 average rating, 240 reviews

Peaceful Secluded Old Rag Retreat

The spacious one bedroom yurt is located high on a forested hillside in the middle of 15+ acres. Come enjoy a natural and serene getaway with all the comforts of home- a full kitchen (ie, all utensils, setting for four), a bathroom with shower and laundry, a queen bedroom, and a queen foldout sofa in the living room by the wood burning stove. The windows roll up from the outside and have permanent screens inside. There is also a BBQ grill, a separate firepit, and WiFi via satellite.

Top guest favorite

The exterior of Rose Cottage is surrounded by lush blooming flowers, creating a colorful welcome. A white picket fence borders the entrance, leading to a rustic wooden door framed by a trellis. Sunlight filters through the green foliage overhead, accentuating the charming garden setting.

Cottage in Sperryville

4.98 out of 5 average rating, 117 reviews

Adorable Rose Cottage in Village of Sperryville

Rose Cottage is a quaint one-of-a-kind retreat in the heart of Sperryville - a charming country village offering shops, galleries, eateries, and more. The property has an excellent location, only 1.5 hours from Washington, DC and convenient to Culpeper, Warrenton, Front Royal and Interstate 66. It is approximately 15 miles from Old Rag Mountain and a 15 minute drive to the Shenandoah National Park, which offers an amazing array of waterfalls, canyons, trails, and hikes.

Top guest favorite

The exterior of a light blue cottage features a welcoming front porch with white railings. A red convertible sports car is parked on the gravel driveway. Lush greenery surrounds the property, complemented by a stone pathway leading to the entrance.

Home in Washington

5 out of 5 average rating, 161 reviews

Mint Cottage at Little Washington

Luxurious appointments, spacious living areas and breathtaking views await you at Mint Cottage at Little Washington! This 1400-square-foot home is just a 5-minute walk or a 1-minute drive to the world-renowned Inn at Little Washington, and a short drive to spectacular hiking in Shenandoah National Park, Three Blacksmiths, craft breweries, distilleries and wineries, shops and so much more. A modern, stylish, and comfortable place to retreat, relax and reinvigorate.

Top guest favorite

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, 204 reviews

The Bunkhouse- 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 bunkhouse is stocked with roasted coffee, farm-fresh eggs, fresh-baked bread, teas and soaps from our incredible local homesteaders and artisans.

Guest favorite

A quaint building with a light grey exterior is accented by turquoise trim and windows, showcasing a charming entryway with double doors. Lush greenery is positioned in front, complementing the urban streetscape. Nearby structures reflect the historic character of the area.

Cottage in Sperryville

4.96 out of 5 average rating, 399 reviews

The River Cottage: Main Street Sperryville, VA

A Quaint private building, originally built as a Blacksmith Shop. Conestoga wagons were made behind this building near the Thornton River.; now guest will enjoy a recently renovated and spacious one room 'suite' right off of Main Street. California King bed with plush bedding. Private bathroom with shower. Kitchenette with hotplate, smoothie maker, coffee maker, and microwave. Private deck that overlooks the Thornton River. Outdoor shower.