Book Holiday Homes in Chester Gap

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Chester Gap

Secluded River Cabin Getaway (Masten Cabin)

Secluded River Cabin Getaway (Masten Cabin)

Strasburg VA
With a stay at this vacation home in Strasburg, you'll be in the mountains, just steps from George Washington National Forest and a 2-minute drive from Shenandoah ...
Opens in a new windowSecluded River Cabin Getaway (Masten Cabin)
Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal

Front Royal VA
The price is AU$314 per night from 22 Mar to 23 Mar
AU$314
22 Mar - 23 Mar
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.
Opens in a new windowMountain View Bungalow in Front Royal
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains

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

Markham VA
With a stay at this vacation home, you'll be centrally located in Linden, within a 15-minute drive of Naked Mountain Winery & Vineyards and Aspen Dale Winery ...
Opens in a new windowBeautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains
Save an average of 15% on thousands of hotels when you're signed in
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 VA
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.
Opens in a new windowCharming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly
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 VA
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.
Opens in a new windowLone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub
Riverfront Retreat

Riverfront Retreat

MAURERTOWN, VA
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 ...
Opens in a new windowRiverfront Retreat
The Nest at Chester Gap

The Nest at Chester Gap

Chester Gap VA
With a stay at this vacation home in Chester Gap, you'll be in the mountains, within a 15-minute drive of Shenandoah National Park and Chester Gap Cellars.
Opens in a new windowThe Nest at Chester Gap
Tranquil Cardinal Hill Cabin- Perfect for Relaxation & Exploration. Pet Friendly

Tranquil Cardinal Hill Cabin- Perfect for Relaxation & Exploration. Pet Friendly

Sperryville VA
With a stay at this vacation home in Sperryville, you'll be within a 15-minute drive of Copper Fox Distillery and River District Arts.
Opens in a new windowTranquil Cardinal Hill Cabin- Perfect for Relaxation & Exploration. Pet Friendly
Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views

Strasburg VA
The price is AU$442 per night from 20 Apr to 21 Apr
AU$442
20 Apr - 21 Apr
includes taxes & fees
Located in Strasburg, this vacation home is within a 5-minute drive of George Washington National Forest and Shenandoah River.
Opens in a new windowNewly renovated Farm cottage with Mountain views
Don't see what you're looking for?
See all available properties in Chester Gap
View all properties
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
158 Holiday Homes
Lowest Price
AU$122
Highest Price
AU$442
Popular accommodation
Secluded River Cabin Getaway (Masten Cabin), Mountain View Bungalow in Front Royal, Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains , Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly, Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub, Riverfront Retreat , The Nest at Chester Gap, Tranquil Cardinal Hill Cabin- Perfect for Relaxation & Exploration. Pet Friendly, Newly renovated Farm cottage with Mountain views

Top trending hotels in Chester Gap

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

2.5 out of 5
195 Kernstown Commons Blvd Winchester VA
Fully refundable
The price is AU$157 per night from 7 Apr to 8 Apr
AU$157
7 Apr - 8 Apr
includes taxes & fees
Located in Winchester, Comfort Inn & Suites Winchester is in a shopping district, within a 10-minute drive of The Kernstown Battlefield and Shenandoah ...
Opens in a new windowComfort Inn & Suites Winchester
Hampton Inn Front Royal

Hampton Inn Front Royal

2.5 out of 5
9800 Winchester Rd Front Royal VA
Fully refundableReserve now, pay when you stay
The price is AU$161 per night from 29 Mar to 30 Mar
AU$161
29 Mar - 30 Mar
includes taxes & fees
With a stay at Hampton Inn Front Royal in Front Royal, you'll be in a national park, within a 15-minute drive of Shenandoah National Park and Shenandoah ...
Opens in a new windowHampton Inn Front Royal
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 out of 5
21 Signal Knob Dr Strasburg VA
Fully refundableReserve now, pay when you stay
The price is AU$122 per night from 30 Mar to 31 Mar
AU$122
30 Mar - 31 Mar
includes taxes & fees
With a stay at Ramada by Wyndham Strasburg/Shenandoah Valley in Strasburg, you'll be in the mountains, just steps from Hupp's Hill Civil War Park and a 3-minute ...
Opens in a new windowRamada by Wyndham Strasburg/Shenandoah Valley
Save an average of 15% on thousands of hotels when you're signed in
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$140 per night from 30 Mar to 31 Mar
AU$140
30 Mar - 31 Mar
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 ...
Opens in a new windowCountry Inn & Suites by Radisson, Winchester, VA
Don't see what you're looking for?
See all available properties in Chester Gap
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.