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

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

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

Luray
When you a stay at this vacation home in Luray, you'll be on the waterfront, just steps from George Washington National Forest and Shenandoah River.
Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!
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Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal

Front Royal
The price is AU$369 per night from 25 Aug to 26 Aug
AU$369
25 Aug - 26 Aug
includes taxes & fees
With a stay at this vacation home in Front Royal, you'll be within a 10-minute drive of Shenandoah National Park and Shenandoah River.
Mountain View Bungalow in Front Royal
Rivers Edge Retreat with spectacular water views, Full kitchen, Games,  Fishing

Rivers Edge Retreat with spectacular water views, Full kitchen, Games, Fishing

Front Royal
With a stay at this vacation home in Front Royal, you'll be on the waterfront, within a 15-minute drive of Shenandoah National Park and Shenandoah River.
Rivers Edge Retreat with spectacular water views, Full kitchen, Games, Fishing
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
On the river ~ hot tub ~ serene river views ~ fire pit

On the river ~ hot tub ~ serene river views ~ fire pit

Strasburg
With a stay at this vacation home in Strasburg, you'll be just steps from George Washington National Forest and Shenandoah River.
On the river ~ hot tub ~ serene river views ~ fire pit
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!
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!
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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
166 Holiday Homes
Lowest Price
AU$115
Highest Price
AU$369
Popular accommodation
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly, Secluded River Cabin Getaway (Masten Cabin), Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!, Mountain View Bungalow in Front Royal, Rivers Edge Retreat with spectacular water views, Full kitchen, Games, Fishing, Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub, On the river ~ hot tub ~ serene river views ~ fire pit, Linden Family Home w/ Yard < 5 Mi to Wineries!, Modern Mountain Retreat w/ Deck + Hot Tub!

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
The price is AU$115 per night from 1 Sept to 2 Sept
AU$115
1 Sept - 2 Sept
includes taxes & fees
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 Winchester

Comfort Inn & Suites Winchester

2.5 out of 5
195 Kernstown Commons Blvd, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is AU$162 per night from 17 Aug to 18 Aug
AU$162
17 Aug - 18 Aug
includes taxes & fees
Located in Winchester, Comfort Inn & Suites Winchester is in a shopping district, a 3-minute drive from Appleland Sports Center and 6 minutes from The Kernstown ...
Comfort Inn & Suites Winchester
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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
The price is AU$159 per night from 13 Aug to 14 Aug
AU$159
13 Aug - 14 Aug
includes taxes & fees
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
Don't see what you're looking for?
See all available properties in Chester Gap
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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.