Book Holiday Homes in Chester Gap

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Featured Holiday Homes in Chester Gap

Secluded River Cabin Getaway (Masten Cabin)

Secluded River Cabin Getaway (Masten Cabin)

Strasburg
With a stay at this vacation home in Strasburg, you'll be in the mountains, just a 1-minute walk from George Washington National Forest and 10 minutes by foot ...
Secluded River Cabin Getaway (Masten Cabin)
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

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

Rileyville
With a stay at this vacation home in Rileyville, you'll be on the waterfront, within a 15-minute drive of Luray Caverns and Warehouse Art Gallery.
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly
Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views

Strasburg
Located in Strasburg, this vacation home is within a 5-minute drive of George Washington National Forest and Shenandoah River.
Newly renovated Farm cottage with Mountain views
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Cozy Country Getaway in the Heart of Upperville

Cozy Country Getaway in the Heart of Upperville

Upperville
Located in Upperville, this vacation home is a 1-minute drive from Upperville Park and 8 minutes from Paris Barns.
Cozy Country Getaway in the Heart of Upperville
Cozy mountain retreat minutes to the river, Luray, and 25 to Shenandoah NP!

Cozy mountain retreat minutes to the river, Luray, and 25 to Shenandoah NP!

Luray
When you stay at this vacation home in Luray, you'll be steps from George Washington National Forest.
Cozy mountain retreat minutes to the river, Luray, and 25 to Shenandoah NP!
Historic Slate Hill School House in Fort Valley, Virginia

Historic Slate Hill School House in Fort Valley, Virginia

Fort Valley
With a stay at this vacation home in Fort Valley, you'll be in the mountains, just steps from George Washington National Forest and a 4-minute drive from Secret ...
Historic Slate Hill School House in Fort Valley, Virginia
Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub

Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub

Rileyville
Located in Rileyville, this vacation home is on a river, a 4-minute drive from Shenandoah River and 5 minutes from George Washington National Forest.
Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub
Linden Family Home w/ Yard < 5 Mi to Wineries!

Linden Family Home w/ Yard < 5 Mi to Wineries!

2 out of 5
Linden
Located in Linden, this vacation home is within a 15-minute walk of George Richard Thompson State Wildlife Management Area and Fox Meadow Winery.
Linden Family Home w/ Yard < 5 Mi to Wineries!
Riverfront Retreat

Riverfront Retreat

MAURERTOWN,
With a stay at this vacation home in Maurertown, you'll be on the waterfront, just steps from Shenandoah River and a 2-minute drive from George Washington National ...
Riverfront Retreat
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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
154 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Secluded River Cabin Getaway (Masten Cabin), Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly, Newly renovated Farm cottage with Mountain views , Cozy Country Getaway in the Heart of Upperville , Cozy mountain retreat minutes to the river, Luray, and 25 to Shenandoah NP! , Historic Slate Hill School House in Fort Valley, Virginia, Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub, Linden Family Home w/ Yard < 5 Mi to Wineries!, Riverfront Retreat

Top trending hotels in Chester Gap

Modern Mountain Retreat w/ Deck + Hot Tub!

Modern Mountain Retreat w/ Deck + Hot Tub!

Chester Gap
With a stay at this vacation home in Chester Gap, you'll be within a 15-minute drive of Shenandoah National Park and Chester Gap Cellars.
Modern Mountain Retreat w/ Deck + Hot Tub!
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 out of 5
21 Signal Knob Dr, GPS: 35 Brandy court, Strasburg, VA
Fully refundableReserve now, pay when you stay
With a stay at Ramada by Wyndham Strasburg/Shenandoah Valley in Strasburg, you'll be in the mountains, a 3-minute walk from Hupp's Hill Civil War Park and a ...
Ramada by Wyndham Strasburg/Shenandoah Valley
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
195 Kernstown Commons Blvd, Winchester, VA
Fully refundableReserve now, pay when you stay
When you stay at Comfort Inn & Suites in Winchester, you'll be in a shopping district, within a 5-minute drive of Appleland Sports Center and The Kernstown ...
Comfort Inn & Suites
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Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

3 out of 5
141 Kernstown Commons Blvd, Winchester, VA
Fully refundable
Located in Winchester, Country Inn & Suites by Radisson, Winchester, VA is a 5-minute drive from The Kernstown Battlefield and 6 minutes from Shenandoah ...
Country Inn & Suites by Radisson, Winchester, VA
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.