Vacation rentals in Chester Gap

A view of Skyhouse from above, showcasing its elevated wooden structure surrounded by lush greenery. The expansive deck features stairs leading down to the ground level, emphasizing the property's integration with nature.

4.91 out of 5 average rating, 465 reviews

Modern River Cabin! Hot Tub*Privacy*Romance*Fun!

Enjoy a River Front Colorful Fall or Cozy Winter Weekend in your BRAND NEW Hot Tub at Skyhouse! Fully-remodeled with million dollar views overlooking the river, steps to the water's edge and floating dock! Relaxation, romance, outdoor adventure or just peace and quiet watching the leaves or snow fall inside on your shearling covered comfy couch with views overlooking the river! Ideal for vacay, workcay, mini-moon, or special occcation. 1 hr from NoVA/DC off I-66, 10 mins to town of Front Royal!

4.96 out of 5 average rating, 158 reviews

A spacious deck offers unobstructed views of rolling hills and valleys, accented by vibrant autumn foliage. The sky is expansive, displaying soft clouds and blue tones. A sleek railing encircles the deck, enhancing the serenity of the natural landscape.

Cottage in Markham

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!

The cabin is framed by lush greenery, showcasing a rustic wooden exterior. A screened-in porch with a railing invites relaxation, while a bird feeder hangs nearby. A set of steps leads up to the entrance, enhancing the warm atmosphere of the tranquil surroundings.

4.99 out of 5 average rating, 259 reviews

Valley View Cabin /10 min from National Park entry

The coziest little cabin to getaway from the hustle and bustle of the city, but only an hour away from Washington DC. Our hope is you enjoy every part of your stay at this little cabin; from enjoying your morning cup of coffee on the screened in porch while watching deer or turkey graze in the yard, or venturing to the quaint Main Street of Front Royal. This town has so much to offer. Only 15 minutes away from Shenandoah National Forest & skyline drive. A perfect place for kayaking & canoeing!

The cabin is nestled in a lush, wooded landscape, surrounded by vibrant greenery and trees reflecting the changing seasons. A gravel driveway leads to the stone facade of the home, which features large windows and a welcoming front porch.

4.97 out of 5 average rating, 167 reviews

Luxury Lodge Fire Pit, Hot Tub, & Sauna

★ Modern LUXE cabin, 4400 sf ★5 mins Shenandoah National Park, Skyline Drive, and Skyline Caverns ★4 mins to nearest trails: Dickey Ridge Trailhead ★2 mins Canoeing, tubing, and kayaking - 2 min ★Arcade & board games, books, 6 ft pool table ★Porches swing & hot tub ★Fire pit with firewood provided ★Sauna ★Electric outdoor grill ★2 Fireplaces (elect.) ★Smart TVs (incl. a 70") ★Fast WiFi ★Well-equipped kitchen with spices ★ Fully enclosed backyard ★5 Min Historic Main Street, Front Royal

Place to stay in Bentonville

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.

4.99 out of 5 average rating, 480 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

4.97 out of 5 average rating, 541 reviews

A two-story cottage is set amidst a wooded backdrop, showcasing a mixture of wood and stone exterior. Large windows and a balcony enhance the home’s charm. A pathway leads to the entrance, and a few outdoor seating options are visible on the lower level.

Cottage in Bentonville

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.

A classic A-frame cabin is surrounded by trees, featuring a spacious deck with comfortable lounge seating. Soft lighting accentuates the inviting outdoor space, while large glass doors provide a glimpse into the cozy interior. The modern roof complements the rustic wooden facade.

4.95 out of 5 average rating, 239 reviews

The Wizard's Chalet • Cozy nature escape • Hot Tub

Looking for a fun getaway in a relaxing, secluded spot? Come visit The Wizard's Chalet, a cozy & upgraded cabin located in the Shenandoah Valley just one mile from Shenandoah River access and a few miles from restaurants, wineries, basketball & volleyball courts, and more! With a fully stocked kitchen, three cozy bedrooms, high speed WIFI, hot tub, and several beautiful outdoor gathering spaces, this magical cabin is perfect for couples, friends, or the entire family!

4.9 out of 5 average rating, 109 reviews

A spacious house is set against a backdrop of rolling hills and deciduous trees, showcasing a blend of natural stone and siding. The property features a well-kept lawn with a pathway leading to the front entrance, providing a welcoming approach to the home.

Home in Front Royal

Mountain Retreat Serenity and Quiet in Shenandoah

Our dacha is your escape from clutter and noise of the every day life, offering great mountain views, just 5 minutes away from Front Royal, Luray Caverns, Shenandoah National Park (our 10 acre property borders the Park), and boat access to Shenandoah river. Plan your hikes and day trips and then come back to enjoy the hot tub. Play table tennis inside our air conditioned/heated garage, badminton outside or simply chill and enjoy the views.

4.96 out of 5 average rating, 140 reviews

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

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.

4.97 out of 5 average rating, 230 reviews

The cabin's exterior is framed by a serene wooded backdrop, showcasing a two-story structure with a front porch and welcoming entrance. Outdoor lighting highlights the pathway and landscape, while the surrounding trees add a sense of tranquility during twilight hours.

Cabin in Linden

Delicious Cabin • Screened Porch, Hot Tub & Charm

Whether you're after a peaceful retreat or a remote work escape, Delicious Cabin has you covered. Enjoy a fully stocked kitchen, fast Wi-Fi, and dedicated workspaces. Unwind in the theater room, relax on the screened porch, or soak in the private hot tub with twilight lighting. Nestled in Virginia Wine Country, this cozy getaway offers the perfect mix of comfort, convenience, and charm for families, couples, or small groups.

4.99 out of 5 average rating, 179 reviews

A charming house is positioned in a scenic area, surrounded by green lawns and distant hills. The exterior features light siding and decorative windows. A deck is visible in the backyard, accompanied by trees and an unobstructed view of the blue sky.

Home in Front Royal

Idle Hour at Chester Gap

Whole house in the foothills of the Shenandoah Mountains and the heart of Virginia wine country. The house is adjacent to Chester Gap Cellars, which offers weekend wine tastings, tours, hiking trails, and spectacular views. Access to the Appalachian Trail is nearby along with Shenandoah National Park, Skyline Drive, and the Shenandoah River. House features expansive back deck, outdoor dining, and private hot tub.