Holiday houses in Chester Gap

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!

Chapel View Nest: Patio, Firepit and Views.

Stay in our secluded getaway on 20 acres with skyline mountain views and stunning sunsets. The main house is perched atop a hill with the English basement attached. Guests will have their own private sunny patio with a gas fire pit and grill. Relax and unwind in this welcoming tucked away spot that is private and tastefully furnished with everything you need for a wonderful stay. Nearby: Christendom College ~1 m Warren Memorial Hospital 2.5 m Shenandoah Park Skyline Dr. 6 m Front Royal 6 m

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 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!

Full Circle Farm Shenandoah Valley No Cleaning Fee

Stay in beautiful Bentonville VA. At the foot of skyline drive and minutes from award winning wineries; near Luray Caverns and the Shenandoah River where you can canoe, raft or kayak. You’ll be on our private property and have complete privacy up the hill from our home. Full kitchen/washer/dryer/TV and WiFi. Explore and enjoy the mountains, river, trails and wine. Pets are welcome. A fee is calculated per pet. $25 per pet. NO CLEANING FEE!

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.

Shenandoah Getaway | Cozy, Clean & Well-Located

Relax in this cozy, private suite near the Blue Ridge Mountains, Appalachian Trail, historic Front Royal, and the new Warren Memorial Hospital. Tucked in a quiet cul-de-sac, it features a queen bed and full-size floor mattress with fresh linens, fast Wi-Fi, Smart TV, stocked bathroom, and light cooking setup. After a day of hiking or sightseeing, unwind by the fire pit or enjoy a quiet evening on your private patio.

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.

Cedarbank • Cabin in Virginia Wine Country

Come visit Virginia wine country and nearby Shenandoah National Park in this modern log cabin. The Cedarbank cabin carries all the conveniences of modern living including updated kitchen and WiFi. Though the grounds are only an hour from Washington DC, Cedarbank feels like a world apart, providing relaxing views and 7 tranquil acres for the perfect rejuvenating country escape. SEE NOTES ABOUT OUR AMENITIES