Holiday rentals in Chester Gap

COZY+SEXY Private Country Escape! HOT TUB & Views~

Look no further for privacy, intimacy, & fun~ Foxy is your perfect escape, located in the Shenandoah Valley & surrounded by a 1000 private acres but only 10 minutes from downtown Winchester. Offering a uniquely glamorous experience, surrounded by all the beauty of nature. Indulge in luxury & tranquility with amenities including your own private patio with hot tub and million dollar views of the Blue Ridge Mountains. Inside, a full chef's kitchen leading to a sexy, opulent master bedroom suite...

Pio- New cabin! Riverfront!

*Built in 2024 * No pets *On the Shenandoah River *River frontage *Stairs into water *Beautifully crafted cabin *4 beds *Electric fireplace *42” smart tv lvgrm, 32”smart tv Br1 *Starlink wifi *Use your streaming service *Cozy and inviting *Deck area with stools and other seating *Fire pit, surrounded by Adirondack chairs *Gas grill *35 min Shen. N. P/ Skyline Dr. *26 minutes to Kennedy Peak Trailhead *5 min to boat launch *29 minutes to groceries *Shop first *26 min to Luray Caverns

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!

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.

Bison Farm - Cabin "Brisa"

Bison Farm cabin in a very secluded section toward the back side of a 300 acre working bison farm. This is a tiny home Park Model with 400 sq. ft. and a nice spacious covered deck providing an outdoor living room. The kitchen has a 2-burner induction cook-top, a convection oven that is also a microwave and a small refrigerator and freezer two drawer unit that has decent space but is not a full sized appliance. Note: bison rotate pastures daily. Please don't expect them in your cabin view.

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

Little Green Cabin on the River

The Little Green Cabin is a beautifully renovated riverfront retreat nestled along one of the Seven Bends of the Shenandoah River between Strasburg and Woodstock—the perfect escape to relax, unwind, and enjoy the outdoors. INSIDE: Full kitchen, 4 beds, cozy furnishings, electric fireplace, Wi-Fi, and oversized windows and doors with plenty of natural light. OUTSIDE: Large screened-in deck, private river access, 2 fire pits, grill, picnic table, hammock, swing set, and horseshoe pit.

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.

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.

The Sparrow Luxury A-Frame w/Hot Tub in Shenandoah

Escape to The Sparrow, a newly built luxury A-Frame nestled in Virginia’s Shenandoah Valley, just a scenic drive from DC. This modern retreat features an African-inspired design, two bedrooms, a full kitchen, a fireplace, a private hot tub, a deck, a workspace, 4K TVs, and a PlayStation 5. Minutes from Luray Caverns, Skyline Drive, and Shenandoah National Park, it’s the perfect base for unforgettable adventure and relaxation.

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.

Mountaintop Retreat with Wood Fired Hot Tub

Doah House is a private retreat perched on a bluff atop the Blue Ridge, with wide views over the Shenandoah Valley. A calm container for rest and observation, the pace softens, shaped by small rituals: lighting the fire, soaking in the wood-fired tub, making coffee by hand. Weather moves through the trees, changing the light, the air, the sound. Each day feels different. The forest shifts, and you might, too.