Book Holiday Homes in Charles Town

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Featured Holiday Homes in Charles Town

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

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

Harpers Ferry WV
With a stay at this vacation home in Harpers Ferry, you'll be a 3-minute walk from Potomac River and within a 5-minute drive of Chesapeake and Ohio Canal.
Opens in a new windowRiverside cottage, minutes from historic Harpers Ferry! Private river access!
Terra Alta - Incredible River Views and Hot Tub!

Terra Alta - Incredible River Views and Hot Tub!

Charles Town WV
The price is AU$616 per night from 8 Jan to 9 Jan
AU$616
8 Jan - 9 Jan 2026
includes taxes & fees
Located in Charles Town, this vacation home is on a river, within a 15-minute drive of Shenandoah River and Shannondale Springs Wildlife Management Area.
Opens in a new windowTerra Alta - Incredible River Views and Hot Tub!
Gruner Bungalow at Otium Cellars

Gruner Bungalow at Otium Cellars

Purcellville VA
Located in Purcellville, this vacation home is in a rural location, a 3-minute drive from Franklin Park and 7 minutes from Fireman's Field.
Opens in a new windowGruner Bungalow at Otium Cellars
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Pets? YES! Hot Tub ★ Gym ★ Firepit ★ Game Room ★ Path to Winery

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

Delaplane VA
Located in Delaplane, this vacation home is in a rural location, within a 15-minute walk of Barrel Oak Winery and Blue Valley Vineyard And Winery.
Opens in a new windowPets? YES! Hot Tub ★ Gym ★ Firepit ★ Game Room ★ Path to Winery
Cozy Cabin w/ Hot Tub & Fire Pit perfect for up to 8 people

Cozy Cabin w/ Hot Tub & Fire Pit perfect for up to 8 people

Harpers Ferry WV
With a stay at this vacation home in Harpers Ferry, you'll be a 3-minute walk from Shannondale Springs Wildlife Management Area and within a 5-minute drive of ...
Opens in a new windowCozy Cabin w/ Hot Tub & Fire Pit perfect for up to 8 people
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Harpers Ferry WV
Located in Harpers Ferry, this vacation home is in the mountains, within a 5-minute drive of Shenandoah River and Bolivar Community Park.
Opens in a new windowLarge Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Harpers Ferry WV
The price is AU$948 per night from 26 Dec to 27 Dec
AU$948
26 Dec - 27 Dec
includes taxes & fees
Located in Harpers Ferry, this vacation home is on a river, within a 5-minute drive of Bolivar Community Park and Shenandoah River.
Opens in a new windowHot Tub, Campfire Ring, Convenient Location, Large Groups!!
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry

Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry

Harpers Ferry WV
The price is AU$767 per night from 22 Dec to 23 Dec
AU$767
22 Dec - 23 Dec
includes taxes & fees
Located in Harpers Ferry, this vacation home is in the mountains, within a 5-minute drive of Shenandoah River and Shannondale Springs Wildlife Management ...
Opens in a new windowCharming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
Historic Queen Anne Family Home w Modern Comforts

Historic Queen Anne Family Home w Modern Comforts

Harpers Ferry WV
The price is AU$587 per night from 4 Jan to 5 Jan
AU$587
4 Jan - 5 Jan 2026
includes taxes & fees
With a stay at this vacation home in Harpers Ferry, you'll be within a 5-minute walk of Harpers Ferry Children's Park and Storer College Campus.
Opens in a new windowHistoric Queen Anne Family Home w Modern Comforts
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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
267 Holiday Homes
Lowest Price
AU$109
Highest Price
AU$948
Popular accommodation
Riverside cottage, minutes from historic Harpers Ferry! Private river access!, Terra Alta - Incredible River Views and Hot Tub!, Gruner Bungalow at Otium Cellars, Pets? YES! Hot Tub ★ Gym ★ Firepit ★ Game Room ★ Path to Winery, Cozy Cabin w/ Hot Tub & Fire Pit perfect for up to 8 people, Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex, Hot Tub, Campfire Ring, Convenient Location, Large Groups!!, Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry, Historic Queen Anne Family Home w Modern Comforts

Top trending hotels in Charles Town

Hampton Inn & Suites Charles Town

Hampton Inn & Suites Charles Town

2.5 out of 5
157 Pimlico Dr Charles Town WV
Fully refundableReserve now, pay when you stay
The price is AU$193 per night from 11 Jan to 12 Jan
AU$193
11 Jan - 12 Jan 2026
includes taxes & fees
A stay at Hampton Inn & Suites Charles Town places you in the heart of Charles Town, within a 5-minute drive of Hollywood Casino at Charles Town Races and Old ...
Opens in a new windowHampton Inn & Suites Charles Town
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 AU$113 per night from 28 Dec to 29 Dec
AU$113
28 Dec - 29 Dec
includes taxes & fees
Located in Charles Town, Days Inn by Wyndham Charles Town/Harpers Ferry is in the entertainment district, within a 15-minute walk of Charles Town Library and ...
Opens in a new windowDays Inn by Wyndham Charles Town/Harpers Ferry
Rodeway Inn & Suites - Charles Town, WV

Rodeway Inn & Suites - Charles Town, WV

2 out of 5
741 E Washington St Charles Town WV
The price is AU$109 per night from 4 Jan to 5 Jan
AU$109
4 Jan - 5 Jan 2026
includes taxes & fees
With a stay at Rodeway Inn & Suites Charles Town in Charles Town, you'll be in the business district, within a 15-minute walk of Charles Town Library and Hollywood ...
Opens in a new windowRodeway Inn & Suites - Charles Town, WV
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Holiday Inn Express Charles Town by IHG

Holiday Inn Express Charles Town by IHG

2.5 out of 5
681 Flowing Springs Rd Charles Town WV
Fully refundable
The price is AU$183 per night from 28 Dec to 29 Dec
AU$183
28 Dec - 29 Dec
includes taxes & fees
Located in Charles Town, Holiday Inn Express Charles Town by IHG is in a rural location, within a 5-minute drive of Hollywood Casino at Charles Town Races and ...
Opens in a new windowHoliday Inn Express Charles Town by IHG
Don't see what you're looking for?
See all available properties in Charles Town
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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.