Vacation rentals in Chester Gap

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Top-rated vacation rentals in Chester Gap

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Guesthouse in Flint Hill

4.97 out of 5 average rating, 148 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 11 – 18

ﺩ.ﺇ471 per night
Guest favorite

Cabin in Front Royal

4.99 out of 5 average rating, 183 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!

Sep 15 – 22

ﺩ.ﺇ793 per night
Guest favorite

Cabin in Linden

4.92 out of 5 average rating, 101 reviews

Hidden Gem on Hidden Valley Lane

Full relax at this unique and tranquil getaway. Cute cabin in a park like setting with a wood burning fire place. A pond and lake view(mostly 3 seasons of the year). There is a hammock and a rope swing to enjoy. Trampoline for the kids. Starlink internet!!! Hike to a natural spring and a small creek that feeds Rappahanock river. Go fishing, hike the Appalachian trails near by or enjoy the list of local wineries. Front Royal is only 15 minutes away as well as Skyline Caverns and Skyline drive.

Sep 22 – 29

ﺩ.ﺇ716 per night

Popular amenities for Chester Gap vacation rentals

Other great vacation rentals in Chester Gap

Guest favorite

Cottage in Woodstock

4.98 out of 5 average rating, 172 reviews

Cottage on Boxwood Lane

Aug 28 – Sep 4

ﺩ.ﺇ345 per night
Guest favorite

Home in Linden

4.96 out of 5 average rating, 108 reviews

Pet Friendly Mountain Home w/hot tub near wineries

Feb 23 – Mar 2

ﺩ.ﺇ966 per night
Guest favorite

Campsite in Front Royal

4.99 out of 5 average rating, 96 reviews

Blue Mountain Hideaway Boutique Camping Experience

Aug 14 – 21

ﺩ.ﺇ646 per night
Guest favorite

Cottage in Warrenton

4.97 out of 5 average rating, 257 reviews

The Soper House-A Quaint & Lovely Country Getaway

Nov 14 – 21

ﺩ.ﺇ427 per night
Guest favorite

Yurt in Etlan

4.95 out of 5 average rating, 189 reviews

Peaceful Secluded Old Rag Retreat

Aug 12 – 19

ﺩ.ﺇ461 per night
Guest favorite

Cottage in Bentonville

4.97 out of 5 average rating, 464 reviews

The Cottage

Nov 4 – 11

ﺩ.ﺇ803 per night
Guest favorite

Cabin in Linden

4.96 out of 5 average rating, 230 reviews

Beau Ridge Cabin.

Sep 24 – Oct 1

ﺩ.ﺇ745 per night
Guest favorite

Chalet in Chester Gap

4.97 out of 5 average rating, 39 reviews

NEW Hike Wine & Dine! Shenandoah NP & Top Wineries

Oct 19 – 26

ﺩ.ﺇ1,749 per night
Guest favorite

Home in Front Royal

4.96 out of 5 average rating, 92 reviews

Cozy house in Shenandoah N.P. City of Front Royal

May 2 – 9

ﺩ.ﺇ479 per night
Guest favorite

Guesthouse in Flint Hill

4.97 out of 5 average rating, 88 reviews

Summer kitchen guesthouse at Caledonia Farm 1812

Aug 11 – 18

ﺩ.ﺇ503 per night
Guest favorite

Guesthouse in Front Royal

4.9 out of 5 average rating, 77 reviews

Cozy Shenandoah River Cabin (10min to Nat’l Park!)

Jun 4 – 11

ﺩ.ﺇ512 per night
Guest favorite

Guest suite in Front Royal

4.92 out of 5 average rating, 73 reviews

Shenandoah Mountain House (Thunder Chalet)

Jun 24 – Jul 1

ﺩ.ﺇ481 per night

Destinations to explore