
Holiday rentals in Chester Gap
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Top-rated holiday rentals in Chester Gap
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A Great Getaway — Foxglove Retreat
Nestled in the Blue Ridge Mountains, "Foxglove Retreat" offers you complete privacy and beautiful vista views of the Shenandoah Valley. Equipped with all the necessities for a relaxed and luxurious experience, the "Foxglove Retreat" is sure to become one of your favorite destinations. "Foxglove Retreat" is ideally located near popular tourist destinations, restaurants and wineries. The Bears Den Trail Center is walking distance for those who would like to explore the beauty of the Blue Ridge Mountains on foot. For those who seek nearby shopping and sightseeing, the quaint village of Middleburg is to the southeast and has many antique shops and elegant boutiques nestled in its historic buildings. To the east is the town of Leesburg featuring the upscale Leesburg Corner Premium Outlets and the Leesburg Farmers’ Market. To the west is the Old Town of Winchester where you will discover charming shops, restaurants, galleries, centuries-old architecture, and historical landmarks.

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

Shenandoah Stargazer with Sauna
Stargazer is the perfect place to get away from it all! The stillness and serenity of being nestled in a bird and wildlife sanctuary is so good for your soul. Watch the sunrise from a hanging basket chair at 2700 feet of elevation, or wait for moonrise and toast spectacular star views! Relax in the sauna after a day filled with hiking and an al fresco meal on the deck. Roast s’mores at the deck fire table or over the side yard fire pit. There's magic in the air at this mountaintop retreat!

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

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.

The Soper House-A Quaint & Lovely Country Getaway
The Soper House is a 1,000 sq.ft. ranch-style home with 3 bedrooms & 1 bath perfectly situated on a 5 acre farmette. Located in Fauquier County, VA. also known as Hunt, Horse & Wine country, each of the bedrooms uniquely displaying these historical themes. This charming cottage has a fully functional eat-in kitchen, a living room & a mudroom with W/D for your use. There are a few neighbors that are visible & we live in the adjacent property & can be easily available.

Cozy Cabin on the river
Enjoy your stay at River's Grace Cabin with the beautiful view of the Shenandoah River from the dock along with fishing, canoeing, tubing or just sit by the campfire relaxing and making smores. Only 10 minutes from our wonderful Luray Caverns and downtown shopping stores and even enjoy the Beautiful Skyline Drive with many overlook views, hiking trials and the beauty of natures deer and bear .. enjoy the country life, make some wonderful memories to last a lifetime.

Bear Mountain Lodge
Bear Mountain Lodge is in the Shenandoah mountains, less than 10 minutes to the Skyline Drive - Front Royal entrance. Enjoy hiking trails, the Shenandoah River, wineries, and all of what Front Royal has to offer. Secluded property offers privacy and peace and quiet. Wifi, Cable TV, toilet paper, paper towels, shower towels, pillows, and sheets are provided. Hot Tub! Both Kuerig and drip coffee machines available. Everyday kitchen essentials included.

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.

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.

Hidden in Shenandoah Valley|Pool|Pets|Fire Pit
Hidden in the Valley sits on 30 private, wooded acres adjoining the George Washington National Forest. This remote property offers a pool, fire pit and foot trails throughout, perfect for your furry companions! If you’re looking for a true escape to nature, surrounded by Virginia’s best hiking trails, wildlife and clear, starry night skies, Hidden in the Valley is the getaway for you!
Popular amenities for Chester Gap holiday rentals
Other great holiday rentals in Chester Gap

The Hayloft

CloudPointe Retreat

River House

Old Rag Cottage - sunny 2 bedroom near everything

New! Zen Cabin in the Clouds

Eagle Roost

The Ladybug Retreat

Luxury Riverfront Home Getaway with Hot Tub
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- Shenandoah National Park
- Luray Caverns
- Stone Tower Winery
- Bryce Resort
- Early Mountain Winery
- Great Falls Park
- Cacapon Resort State Park
- Prince Michel Winery
- Tysons Corner Center
- George Mason University
- Jiffy Lube Live
- Big Cork Vineyards
- Harpers Ferry National Historical Park
- Sky Meadows State Park
- Shenandoah River Outfitters
- James Madison University
- Cooter's Place
- Mosaic District
- Bluemont Vineyard
- White Lotus Eco Spa Retreat
- Antietam National Battlefield
- Reston Town Center
- James Madison's Montpelier
- Skyline Caverns




