Vacation rentals in Sperryville

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Top-rated vacation rentals in Sperryville

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Top guest favorite

A compact coffee station features a red Keurig machine on a wooden table, accompanied by a selection of coffee supplies. Four white mugs hang above the table, and a small sign reading 'Welcome' adds a friendly touch to the area. A trash can is positioned nearby.

Guesthouse in Flint Hill

4.97 out of 5 average rating, 173 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

The image features a spacious hot tub filled with clear water, set against a backdrop of lush green trees and a blue sky. The serene outdoor setting invites relaxation and offers scenic views of the surrounding landscape.

Cabin in Bentonville

4.96 out of 5 average rating, 170 reviews

Timber Creek: Falls - A Shenandoah Cabin

Nestled on 8 acres, the Timber Creek Falls A-frame sits on the Shenandoah National Park border overlooking a beautiful cascading waterfall. A 90-min drive from DC, this cabin getaway will have you unwinding in tranquility. A hot tub offers views stretching 50mi to West Virginia on a clear day, and the closest neighbor is a half mile away. A truly private retreat comes w/ modern conveniences including: EV charger, smart devices, flat-screen TV, standing desk, wood burning stove & spa bathrobes.

Top guest favorite

A tranquil sitting area is positioned beside a gently flowing stream, surrounded by lush greenery. Two black chairs rest on a gravel surface, with natural rocks and trees providing a serene backdrop. Sunlight filters through the leaves, creating a calm and peaceful atmosphere.

Guesthouse in Syria

4.96 out of 5 average rating, 386 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

An informational page detailing the history of Washington, Virginia. It highlights key dates such as the survey by George Washington in 1749, establishment as a town in 1796, and incorporation as a municipality in 1894, formatted with clear headings and dates.

Home in Washington

4.98 out of 5 average rating, 225 reviews

Wash/across INN Completely Private 0.5House 2 bedr

Completely Private Half of Colonial House-No Shared Space! We warmly invite you to enjoy 2 cozy upstairs bedrooms, each with comfy queen beds,1.5 bathrooms . Spacious living room on the first floor featuring a comfy sofa & TV,Fully equipped kitchen, Free fast Wi-Fi.Relax on the lovely front porch with a swing and enjoy the peace of a safe, quiet neighborhood with ample free parking. Perfect for couples, small families seeking a private, comfortable retreat near The Inn at Little Washington.

Top guest favorite

Cottage in Bentonville

4.97 out of 5 average rating, 531 reviews

The Cottage

Need some time to refresh? Spending time in the foothills of the Skyline Drive at our cozy cottage may be for you. Well behaved dogs are welcome but not on furniture. The driveway is long and home is very secluded. Winter access will be subject to weather conditions. Driveway does not get plowed and gets rutty during rainy periods. Cell service is spotty on Browntown road. The cottage has a landline and wifi. Use your wifi calling feature for cell phone use. More info under photos.

Guest favorite

Two horses graze peacefully in a lush green field, framed by rows of grapevines. The backdrop features rolling hills under a clear blue sky, dotted with fluffy white clouds. The serene landscape captures the essence of the vineyard's tranquil setting.

Farm stay in Sperryville

4.9 out of 5 average rating, 148 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.

Guest favorite

A panoramic view of the Virginia Piedmont is showcased, revealing layers of rolling hills and valleys. A hand is extended towards the landscape, pointing towards a distant hill, while clouds drift across the sky, creating a serene atmosphere. The lush greenery of the forest is prominent.

Yurt in Etlan

4.96 out of 5 average rating, 231 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 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, 151 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 colorful sunset fills the sky with hues of orange and pink, viewed from the property. The silhouette of the house is complemented by the warm light from the windows. Green foliage and flowers adorn the foreground, enhancing the serene atmosphere.

Guesthouse in Boston

4.98 out of 5 average rating, 194 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

An exterior view of a white farmhouse with a green metal roof is showcased, featuring a screened porch with white railings. Adjacent to the house, a traditional barn structure is visible, surrounded by a grassy area and trees, reflecting the serene countryside landscape.

Home in Woodville

4.86 out of 5 average rating, 185 reviews

Walnut Run Farm - Private & Quiet - Sperryville

A beautiful old farm in the foothills of the Blue Ridge Mountains. The 1880 farmhouse sits on a small stream that runs through the entire fifty-five acre property. The house is clean, minimally decorated, with pasture views out of every window. The farm is located 80 miles from Washington DC and just down the road from Sperryville, Shenandoah National Park, Old Rag Mountain, Luray Caverns, The Inn at Little Washington and other local attractions.

Guest favorite

The stone fireplace serves as a focal point in the living room, showcasing original cooking tools and pots arranged above and beside the hearth. A sturdy wooden mantel rests above, and the rustic texture of the surrounding walls contributes to the historical ambiance.

Guesthouse in Flint Hill

4.96 out of 5 average rating, 130 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

A tranquil river flows through a lush, green landscape. Smooth stones line the riverbed, with gentle ripples of water reflecting the surrounding trees and foliage. Sunlight filters through the leaves, creating a serene atmosphere along the banks.

Cottage in Sperryville

4.96 out of 5 average rating, 393 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. Queen 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.