Vacation rentals in Chester Gap

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Top-rated vacation rentals in Chester Gap

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Guest favorite

Guesthouse in Flint Hill

4.97 out of 5 average rating, 150 reviews

Three Meadows Farm, outdoor views, great location

As you approach the driveway on the private lane, you'll be welcomed by beautiful meadows and rolling hills. Set on 10 acres in a shaded, forest of mature trees it's comfortable year round. There are beautiful mountain views from several locations on the property. It's peaceful and quiet here most of the time. We're conveniently located just minutes from Flint Hill, not much farther to Washington VA, Sperryville and Front Royal. It's a two bedroom/one bathroom apartment above a detached garage.

Oct 8 – 13

€ 177 per night

Guest favorite

Cabin in Front Royal

4.88 out of 5 average rating, 329 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!

Jan 22 – 29

€ 224 per night

Guest favorite

Guesthouse in Marshall

5.0 out of 5 average rating, 101 reviews

Moon Hold Cottage - Retreat, Refresh, Recharge

Unplug from city life and venture out to our small organic farm. Spend a night or two in the private guest cottage while enjoying nearby vineyards and restaurants. Spend the day browsing in the local antique shops or relax on the farm and watch nature's display (butterflies, birds, an occasional critter.) We may be working in the garden or putting up hay. We're always glad to share a bit of the harvest when the vegetables are ripe, so you can take some home to enjoy. All are welcome here!

Jul 2 – 9

€ 121 per night

Guest favorite

Place to stay in Bentonville

4.98 out of 5 average rating, 386 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. A large front porch with swing is waiting for you. @walnuthillcabin

Mar 19 – 26

€ 186 per night

Guest favorite

Apartment in The Plains

4.98 out of 5 average rating, 447 reviews

Rose End

Need to social distance? Our quiet country studio is far enough from Washington DC to get away without being gone. Ideal for grabbing some space, a long run, a bike ride, or visiting local wineries. The Appalachian Trail is just a stone's throw away. We respect your privacy. No smoking is allowed and internet access is from your own hot-spot. The studio includes a satellite TV, refrigerator, microwave, and coffee maker. The queen-size bed and skylight make Rose End a cozy escape.

Aug 15 – 22

€ 90 per night

Guest favorite

Cottage in Warrenton

4.97 out of 5 average rating, 260 reviews

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.

Oct 2 – 9

€ 133 per night

Guest favorite

Farm stay in Warrenton

4.98 out of 5 average rating, 521 reviews

Winters Retreat Farm Cottage - Entire house

Need a change of view? Unplug, and relax in this private cottage. Watch for deer, turkeys and maybe even a bear in the field from the sun room, or take a hike around the homestead. Centered in Fauquier's wine country it is ideal for the weekend escape, and day trips West to the mountains, East to DC or points south. Perfect for those extra reunion family members, wedding guest accommodations, or the "Hafeway overnighter" traveling North or South.

Sep 28 – Oct 5

€ 120 per night

Guest favorite

Chalet in Front Royal

4.96 out of 5 average rating, 179 reviews

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.

Jan 21 – 28

€ 375 per night

Guest favorite

Apartment in Bentonville

4.98 out of 5 average rating, 238 reviews

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!

Aug 21 – 28

€ 180 per night

Guest favorite

Cabin in Front Royal

4.98 out of 5 average rating, 101 reviews

Luxury Lodge with Fire Pit & Hot Tub in Shenandoah

Welcome to Wildflower Lodge, your luxury getaway nestled on 3 acres, just 5 minutes from Shenandoah National Park and Skyline Drive. An hour and a half from Washington DC, our modern lodge is perfect for family and friends. Enjoy a fully enclosed backyard, and explore local wineries, breweries, and Shenandoah Valley's outdoor attractions.d Offering comfort and adventure, it's the ideal spot for those seeking to relax or explore the great

Mar 25 – Apr 1

€ 507 per night

Guest favorite

Cabin in Linden

4.96 out of 5 average rating, 230 reviews

Beau Ridge Cabin.

Cozy VIRGINIA WINE COUNTRY MOUNTAINTOP cabin with breathtaking views of the SHENANDOAH VALLEY, beautiful sunsets, starry nights, abundant wildlife and flora. Planning to elope or renew your vows??? Valley Vows can accommodate you at the cabin, just bring your marriage license. Concerns of traveling BEAU RIDGE CABIN is thoroughly cleaned and sanitized following Airbnb's strict, new enhanced COVID -19 protocol.

Sep 11 – 18

€ 231 per night

Guest favorite

Home in Front Royal

4.99 out of 5 average rating, 148 reviews

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.

Feb 17 – 24

€ 321 per night