Book Holiday Homes in Chester Gap
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Featured Holiday Homes in Chester Gap

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains

Secluded River Cabin Getaway (Masten Cabin)

5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine

Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!

Pets? YES! Hot Tub ★ Gym ★ Firepit ★ Game Room ★ Path to Winery

Fall Getaway on the Shenandoah River near Luray, VA highspeed WiFi

Waterfront Log Home Hot Tub Flat yard w/ Volleyball Fire Pit & Tubes for Floating

Riverfront Retreat
Chester Gap Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chester Gap vacation homes are the perfect way for you to wing it.
Holiday houses in Chester Gap let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chester Gap in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chester Gap adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chester Gap with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chester Gap vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Chester Gap Holiday Homes essential information
Accommodation | 149 Holiday Homes |
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Lowest Price | NZ$169 |
Highest Price | NZ$1,160 |
Popular accommodation | Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly, Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains , Secluded River Cabin Getaway (Masten Cabin), 5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine, Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!, Pets? YES! Hot Tub ★ Gym ★ Firepit ★ Game Room ★ Path to Winery, Fall Getaway on the Shenandoah River near Luray, VA highspeed WiFi, Waterfront Log Home Hot Tub Flat yard w/ Volleyball Fire Pit & Tubes for Floating, Riverfront Retreat |
Top trending hotels in Chester Gap

Modern Mountain Retreat w/ Deck + Hot Tub!

Comfort Inn & Suites

DoubleTree by Hilton Front Royal Blue Ridge Shadows

Country Inn & Suites by Radisson, Winchester, VA
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.