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 12 – 19

G$26,842 GYD per night

Guest favorite

Guesthouse in Marshall

5.0 out of 5 average rating, 102 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!

Aug 19 – 26

G$25,848 GYD per night

Guest favorite

Home in Edinburg

4.98 out of 5 average rating, 353 reviews

Jay Birds Nest - Pet Friendly

Welcome to Jay Birds nest, located in the historic town of Edinburg, Virginia. Just 1.5 miles from I-81. Fully equipped with all the comforts of home and gorgeous mountain views. Enjoy having the entire house to yourself with sleeping for 6 with 2 queen bedrooms and 1 full bedroom and one full bath. Plenty of parking with room for two cars, one under a car port. Have your morning coffee in the relaxing sunroom or in the outdoor seating area. Just a quick walk away from the Shenandoah River.

Mar 2 – 9

G$22,014 GYD per night

Guest favorite

Cottage in Bentonville

4.97 out of 5 average rating, 469 reviews

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.

Mar 4 – 11

G$43,807 GYD per night

Guest favorite

Place to stay in Bentonville

4.98 out of 5 average rating, 387 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

Nov 27 – Dec 4

G$34,665 GYD 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 2 – 9

G$18,415 GYD per night

Guest favorite

Cottage in Warrenton

4.97 out of 5 average rating, 262 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.

Aug 25 – Sep 1

G$24,236 GYD per night

Guest favorite

Cabin in Lost River

4.96 out of 5 average rating, 112 reviews

Rustic and stylish mountain getaway

The Little Black Cabin is everything you've been dreaming about for your cozy mountain getaway! Take in sweeping views, curl up by the fireplace, or make s'mores at the fire pit. Whip up a gourmet meal in the small but well-appointed kitchen. Three dining areas offer options for dinner -- or a remote office, thanks to wifi. Sample nearby hiking, yoga, and farmers' market. We're a little rustic (no TV, AC, microwave, laundry or dishwasher) and a lot stylish!

Dec 30 – Jan 6

G$20,195 GYD per night

Guest favorite

Farm stay in Warrenton

4.98 out of 5 average rating, 525 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 2 – 9

G$23,808 GYD per night

Guest favorite

Chalet in Front Royal

4.96 out of 5 average rating, 180 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.

Apr 1 – 8

G$70,345 GYD per night

Guest favorite

Apartment in Bentonville

4.98 out of 5 average rating, 239 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!

Sep 18 – 25

G$35,790 GYD per night

Guest favorite

Guesthouse in Warrenton

4.98 out of 5 average rating, 251 reviews

The Alton Cottage -a luxury country retreat

The Alton Cottage is a charming, newly refurbished 1820s guest house- formerly a summer kitchen to the original farm house. Views are of rolling fields and their bovine occupants. We are within 30 minutes of almost 20 wineries and another 20 breweries, 5 min to Airlie, and only 5 mi to Old Town Warrenton. We are also close to several antique stores, farmers markets and Shenandoah National Park. We strive to make every guests stay special.

Jun 11 – 18

G$28,995 GYD per night