Vacation rentals in Chester Gap

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Top-rated vacation rentals in Chester Gap

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Guest favorite

Cottage in Markham

4.94 out of 5 average rating, 103 reviews

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!

Jan 8 – 15

G$59,617 GYD per night

Guest favorite

Guesthouse in Flint Hill

4.97 out of 5 average rating, 151 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.

Sep 4 – 11

G$27,026 GYD per night

Guest favorite

Cabin in Front Royal

4.99 out of 5 average rating, 187 reviews

Valley View Cabin

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!

Oct 19 – 26

G$45,176 GYD per night

Guest favorite

Guesthouse in Marshall

5.0 out of 5 average rating, 103 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!

Oct 8 – 15

G$25,420 GYD per night

Guest favorite

Cottage in Winchester

4.9 out of 5 average rating, 101 reviews

Lockley Cottage at Historic Perry Farm

Peace and tranquility await you at a quaint cottage on historic Perry Farm, where the original 19th century farmhouse still stands today. Stroll several acres of land and enjoy pastoral views while you unwind at this peaceful historic property in the hills of northern Shenandoah Valley. This rural retreat is easily accessed from I-81 and located a short 10-minute drive from historic downtown Winchester. Enjoy local wineries, breweries, farm markets, and the renowned Apple Blossom Festival.

Jul 19 – 26

G$15,556 GYD per night

Guest favorite

Home in Edinburg

4.98 out of 5 average rating, 360 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.

Sep 16 – 23

G$22,345 GYD per night

Guest favorite

Cottage in Bentonville

4.97 out of 5 average rating, 471 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 3 – 10

G$43,782 GYD per night

Guest favorite

Place to stay in Bentonville

4.98 out of 5 average rating, 390 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 26 – Apr 2

G$33,540 GYD per night

Guest favorite

Apartment in The Plains

4.98 out of 5 average rating, 451 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.

Oct 8 – 15

G$18,418 GYD per night

Guest favorite

Farm stay in Warrenton

4.98 out of 5 average rating, 527 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.

Aug 7 – 14

G$24,425 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.

Nov 24 – Dec 1

G$77,555 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!

Jul 7 – 14

G$36,273 GYD per night