Book Holiday Homes in Charles Town

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Featured Holiday Homes in Charles Town

Breathtaking views  with an  indoor private pool, come escape with us

Breathtaking views with an indoor private pool, come escape with us

Bluemont
Stay at this vacation home in Bluemont. Enjoy private pools, a fitness center, and a garden. Our guests praise the pool and the helpful staff in our reviews. ...
Breathtaking views with an indoor private pool, come escape with us
Charming "Cream of the Crop" Cape ~❤️of Middletown

Charming "Cream of the Crop" Cape ~❤️of Middletown

Middletown
The price is NZ$551 per night from 6 Jan to 7 Jan
NZ$551
includes taxes & fees
6 Jan - 7 Jan 2025
Stay at this vacation home in Middletown. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Orchid Cellar Winery and ...
Charming "Cream of the Crop" Cape ~❤️of Middletown
Terra Alta - Incredible River Views and Hot Tub!

Terra Alta - Incredible River Views and Hot Tub!

Charles Town
The price is NZ$1,133 per night from 26 Dec to 27 Dec
NZ$1,133
includes taxes & fees
26 Dec - 27 Dec
Book a stay at this family-friendly vacation home in Charles Town. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Hollywood Casino ...
Terra Alta - Incredible River Views and Hot Tub!
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Charles Town Home w/ Private Pool & Hot Tub

Charles Town Home w/ Private Pool & Hot Tub

Charles Town
Book a stay at this family-friendly vacation home in Charles Town. Enjoy private pools, patios, and cable/satellite TV service. Popular attractions Hollywood ...
Charles Town Home w/ Private Pool & Hot Tub
 Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!

Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!

Marshall
Book a stay at this business-friendly vacation home in Marshall. Enjoy free WiFi, a garden, and concierge services. Popular attractions Upperville Park and Glenwood ...
Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!
YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated  Sunny Luxurious Indoor

YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor

Middleburg
Stay at this vacation home in Middleburg. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Greenhill Winery & Vineyards and Red Fox ...
YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor
Charming 3-Bedroom Home in Harpers Ferry Historic District: Walk to Attractions!

Charming 3-Bedroom Home in Harpers Ferry Historic District: Walk to Attractions!

Harpers Ferry
Stay at this vacation home in Harpers Ferry. Enjoy free WiFi, an in-room coffeemaker, and in-room fireplaces. Popular attractions Appalachian Trail Conservancy ...
Charming 3-Bedroom Home in Harpers Ferry Historic District: Walk to Attractions!
Riverside cottage, minutes from historic Harpers Ferry!  Private river access!

Riverside cottage, minutes from historic Harpers Ferry! Private river access!

Harpers Ferry
The price is NZ$390 per night from 26 Dec to 27 Dec
NZ$390
includes taxes & fees
26 Dec - 27 Dec
Stay at this vacation home in Harpers Ferry. Enjoy free WiFi, patios, and an in-room coffeemaker. Our guests praise the helpful staff in our reviews. Popular ...
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

Harpers Ferry
Stay at this vacation home in Harpers Ferry. Enjoy free WiFi, a garden, and patios. Popular attractions John Brown Wax Museum and John Brown's Fort are located ...
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
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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.

Charles Town 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 Charles Town vacation homes are the perfect way for you to wing it.

Holiday houses in Charles Town 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 Charles Town 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 Charles Town adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Charles Town 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 Charles Town 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.

Charles Town Holiday Homes essential information

Accommodation
223 Holiday Homes
Lowest Price
NZ$133
Highest Price
NZ$1,133
Popular accommodation
Breathtaking views with an indoor private pool, come escape with us, Charming "Cream of the Crop" Cape ~❤️of Middletown, Terra Alta - Incredible River Views and Hot Tub!, Charles Town Home w/ Private Pool & Hot Tub, Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!, YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor, Charming 3-Bedroom Home in Harpers Ferry Historic District: Walk to Attractions!, Riverside cottage, minutes from historic Harpers Ferry! Private river access!, Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

Top trending hotels in Charles Town

The Inn at Charles Town

The Inn at Charles Town

3 out of 5
100 Hollywood Dr, Charles Town, WV
Fully refundableReserve now, pay when you stay
The price is NZ$236 per night from 1 Jan to 2 Jan
NZ$236
includes taxes & fees
1 Jan - 2 Jan 2025
Stay at this 3-star business-friendly hotel in Charles Town. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
The Inn at Charles Town
Rodeway Inn & Suites - Charles Town, WV

Rodeway Inn & Suites - Charles Town, WV

2 out of 5
741 E Washington St, Charles Town, WV
Fully refundableReserve now, pay when you stay
The price is NZ$135 per night from 25 Dec to 26 Dec
NZ$135
includes taxes & fees
25 Dec - 26 Dec
Book a stay at this business-friendly motel in Charles Town. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Rodeway Inn & Suites - Charles Town, WV
Home2 Suites by Hilton Charles Town

Home2 Suites by Hilton Charles Town

3 out of 5
70 Jefferson Crossing Way, Charles Town, WV
Fully refundableReserve now, pay when you stay
The price is NZ$285 per night from 1 Jan to 2 Jan
NZ$285
includes taxes & fees
1 Jan - 2 Jan 2025
Stay at this 3-star business-friendly hotel in Charles Town. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Home2 Suites by Hilton Charles Town
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Days Inn by Wyndham Charles Town/Harpers Ferry

Days Inn by Wyndham Charles Town/Harpers Ferry

2 out of 5
642 E Washington Street, Charles Town, WV
Fully refundableReserve now, pay when you stay
The price is NZ$133 per night from 6 Jan to 7 Jan
NZ$133
includes taxes & fees
6 Jan - 7 Jan 2025
Book a stay at this business-friendly hotel in Charles Town. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Days Inn by Wyndham Charles Town/Harpers Ferry
Don't see what you're looking for?
See all available properties in Charles Town
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.