Cottage holiday rentals in Sperryville

Sunrise Cottage in Wine Country

The place for nature lovers and the audiophile! Newly renovated cottage with queen bed and queen sleeper sofa! Situated on five acres, at Sunrise Cottage you can see no other dwellings except those in the valley far below. Lay in bed and watch the sun rise from the East. 60 mile views with a monarch waystation off the deck. Relax in the hot tub or sit around the fire pit. Bathroom has a spa feel with rainfall showerhead. Close to Marriott Ranch for horse trail rides and surrounded by wineries!

Idyllic Cottage Retreat

⭐️ Condé Nast Traveler Approved ⭐️ Cozy cottage nestled on a historic 400-acre Blue Ridge Mountain farm abutting Shenandoah National Park. Every space inside this cozy cottage is creatively styled, with tons of perfectly imperfect charm. Outside, a hammock beneath the elm trees, fire pit and grill, all allow for enjoying the splendor of this peaceful enclave. Excellent day-tripping to many of central Virginia's celebrated wineries and breweries, as well as scenic drives and hiking trails.

The Cottage at B and M Journey Farm

Take it easy at this unique and tranquil getaway. The Cottage at B and M Journey Farm is rustic and cozy and placed on a working farmette. Enjoy evening walks through pollinator spaces and the vineyard. Rise with the sunrise over New Market Gap and settle in at the fire pit overlooking the vineyard. In cooler months enjoy the cabin’s gas fireplace (if you wish). Hiking trails are nearby on New Market Mountain or the Shenandoah National Park. Food and wineries may be found within a short drive.

Sweet Scenes Cottage

Savor the mountain scenery at this tranquil escape on the South Fork of the Shenandoah River. The large covered deck is the perfect place to sip your coffee or watch the wildlife. The stars are amazing! Bring your canoes & kayaks & access the river from the common area. Luray Caverns is a popular attraction just 10 minutes away, & miles of hiking trails and waterfalls await 15 minutes away in the Shenandoah National Forest. Skyline Drive astounds with valley views, also just 15 minutes away.

Creekside Cottage Near Hiking

Creekside Cottage is the perfect getaway home to escape to the beautiful Blue Ridge Mountains. This newly renovated luxury cottage is only minutes from hiking trails and just a short drive from the Old Rag trailhead. Nestled in Syria, Virginia, this comfortable space features updated amenities such as a rain shower, a well appointed kitchen, plenty of lounge spaces, board games for days, and a central wood burning stove. Just a few steps out the back door you'll find your own private creek.

Shenandoah Riverfront and Mountain View Cottage

The Misty River Cottage is located on one of the seven bends of the Shenandoah River and at the base of the Massanutten Mountain. It was designed, built and furnished with the goal of being one of the nicest options in the Shenandoah Valley. With views of the river and mountains from every room. Ensuite bathrooms in each of the two bedrooms. A custom built bunk bed for larger groups. Heated floors, spectacular outdoor space and direct river access all within a short drive to Woodstock.

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.

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.

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.

Hot Tub~WiFi~Views

Escape to a charming one-bedroom Blue Horizon Cottage nestled in the serene mountains, offering breathtaking views of the Blue Ridge Mountain. Relax in the oversized hot tub on the spacious deck, surrounded by National Forrest and nature's beauty. This cozy retreat provides the perfect blend of comfort and tranquility. With easy vehicle accessibility, you can easily reach this idyllic getaway for a peaceful and rejuvenating experience.

The Cottage at Old Salem School

Charming, fully renovated 1800's school house conveniently located between Culpeper and Sperryville. Enjoy dining on the covered porch or patio and sharing stories at the fire pit, or explore the many local breweries, wineries, or world class restaurants nearby. Easily accessible from Skyline Drive or Northern Virginia, this private cabin has everything you need to relax after a day of hiking, shopping, or working.

Amy's Place

Time for a quiet retreat to the country. Fall is here! Good time to hit the hiking trails. Here's a totally modern cottage for up to four people for whom camping and even our Hayloft Cottage may seem a bit too rustic. The back door opens up to a porch and a spacious 1.5 acres of fenced-in area (shared with Hayloft dog owners and our mutts), perfect for your four-footed friends (dogs only; limit 2).