Book Holiday Homes in Charlestown
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Featured Holiday Homes in Charlestown

Charming shotgun home, in the heart of Louisville!

Enchanting, energizing, and enjoyable!

The Curated Chateau—Minutes from Louisville

Derby Cigar & Bourbon Lounge Group Stays in Louisville Kentucky

Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.

Spacious and Beautiful home near downtown Louisville, Kentucky.

3 Bed, 3 Bath Loft in Downtown Louisville! Amazing River Views! Private Deck!

Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!

ꕥLuxꕥHeated* Pool/Hot Tub/Gamerooms/Firepit/Outdoor Shower/Bunks
Charlestown 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 Charlestown vacation homes are the perfect way for you to wing it.
Holiday houses in Charlestown 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 Charlestown 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 Charlestown adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Charlestown 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 Charlestown 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.
Charlestown Holiday Homes essential information
Accommodation | 960 Holiday Homes |
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Lowest Price | AU$104 |
Highest Price | AU$1,915 |
Popular accommodation | Charming shotgun home, in the heart of Louisville!, Enchanting, energizing, and enjoyable!, The Curated Chateau—Minutes from Louisville, Derby Cigar & Bourbon Lounge Group Stays in Louisville Kentucky, Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard. , Spacious and Beautiful home near downtown Louisville, Kentucky., 3 Bed, 3 Bath Loft in Downtown Louisville! Amazing River Views! Private Deck!, Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!, ꕥLuxꕥHeated* Pool/Hot Tub/Gamerooms/Firepit/Outdoor Shower/Bunks |
Holiday Homes in Charlestown
Top Locations for Holiday Homes in Charlestown
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Radisson Hotel Louisville North

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Derby City Gaming & Hotel - A Churchill Downs Property
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^Subject to availability and chosen travel dates.