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
Stay at this vacation home in Rileyville. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Chalybeate Spring and Elkwallow Picnic ...
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

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

Markham
Book a stay at this family-friendly vacation home in Linden. Enjoy free WiFi, a garden, and patios. Popular attractions Tuckers Lane Trailhead and Fox Meadow ...
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains
Secluded River Cabin Getaway (Masten Cabin)

Secluded River Cabin Getaway (Masten Cabin)

Strasburg
Stay at this vacation home in Strasburg. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Secret Passage Ranch and Strasburg Museum are ...
Secluded River Cabin Getaway (Masten Cabin)
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5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine

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

Delaplane
Book a stay at this family-friendly vacation home in Delaplane. Enjoy free WiFi, a garden, and a pool table. Popular attractions RdV Vineyards and Aspen Dale ...
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!

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

Luray
Book a stay at this family-friendly vacation home in Luray. Enjoy free WiFi, a water park, and a garden. Popular attractions Chalybeate Spring and Fort Valley ...
Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!
Pets? YES! Hot Tub ★ Gym ★ Firepit ★ Game Room ★ Path to Winery

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

Delaplane
Book a stay at this family-friendly vacation home in Delaplane. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Blue Valley Vineyard And ...
Pets? YES! Hot Tub ★ Gym ★ Firepit ★ Game Room ★ Path to Winery
Fall Getaway on the Shenandoah River near Luray, VA highspeed WiFi

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

Rileyville
Book a stay at this family-friendly vacation home in Rileyville. Enjoy a water park, a garden, and a pool table. Popular attractions Chalybeate Spring and Fort ...
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

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

Maurertown
The price is NZ$1,160 per night from 6 Apr to 7 Apr
NZ$1,160
includes taxes & fees
6 Apr - 7 Apr
Stay at this vacation home in Maurertown. Enjoy free WiFi, patios, and an in-room coffeemaker. Our guests praise the helpful staff in our reviews. Popular attractions ...
Waterfront Log Home Hot Tub Flat yard w/ Volleyball Fire Pit & Tubes for Floating
Riverfront Retreat

Riverfront Retreat

MAURERTOWN,
Stay at this vacation home in Maurertown. Enjoy free WiFi, a garden, and patios. Popular attractions Shenandoah County Park and Woodstock Tower Observation Site ...
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
149 Holiday Homes
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!

Modern Mountain Retreat w/ Deck + Hot Tub!

Chester Gap
Book a stay at this family-friendly vacation home in Chester Gap. Enjoy patios, cable/satellite TV service, and in-room washers/dryers. Popular attractions Chester ...
Modern Mountain Retreat w/ Deck + Hot Tub!
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
195 Kernstown Commons Blvd, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is NZ$169 per night from 6 Apr to 7 Apr
NZ$169
includes taxes & fees
6 Apr - 7 Apr
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Comfort Inn & Suites
DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows

4 out of 5
111 Hospitality Drive, Front Royal, VA
Fully refundableReserve now, pay when you stay
The price is NZ$217 per night from 13 Apr to 14 Apr
NZ$217
includes taxes & fees
13 Apr - 14 Apr
Stay at this 4-star golf hotel in Front Royal. Enjoy free WiFi, free parking, and a golf course. Our guests praise the helpful staff and the clean rooms in our ...
DoubleTree by Hilton Front Royal Blue Ridge Shadows
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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 NZ$169 per night from 10 Apr to 11 Apr
NZ$169
includes taxes & fees
10 Apr - 11 Apr
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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.

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