Book Holiday Homes in Charlestown

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Featured Holiday Homes in Charlestown

Charming shotgun home, in the heart of Louisville!

Charming shotgun home, in the heart of Louisville!

Louisville
With a stay at this vacation home in Louisville (Merriwether), you'll be within a 5-minute drive of University of Louisville and Fourth Street Live!.
Charming shotgun home, in the heart of Louisville!
Enchanting, energizing, and enjoyable!

Enchanting, energizing, and enjoyable!

Buckner
When you stay at this vacation home in Buckner, you'll be within a 10-minute drive of Wendell Moore Park and Reformatory Lake.
Enchanting, energizing, and enjoyable!
The Curated Chateau—Minutes from Louisville

The Curated Chateau—Minutes from Louisville

New Albany
With a stay at this vacation home, you'll be centrally located in New Albany, within a 10-minute drive of Louisville Slugger Museum and Kentucky International ...
The Curated Chateau—Minutes from Louisville
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Derby Cigar & Bourbon Lounge Group Stays in Louisville Kentucky

Derby Cigar & Bourbon Lounge Group Stays in Louisville Kentucky

Louisville
The price is AU$929 per night from 14 Apr to 15 Apr
AU$929
includes taxes & fees
14 Apr - 15 Apr
With a stay at this vacation home in Louisville (Shelby Park), you'll be within a 5-minute drive of University of Louisville and Fourth Street Live!.
Derby Cigar & Bourbon Lounge Group Stays in Louisville Kentucky
Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.

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

New Albany
The price is AU$329 per night from 8 Apr to 9 Apr
AU$329
includes taxes & fees
8 Apr - 9 Apr
With a stay at this vacation home in New Albany, you'll be within a 10-minute drive of Fourth Street Live! and Louisville Slugger Museum.
Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.
Spacious and Beautiful home near downtown Louisville, Kentucky.

Spacious and Beautiful home near downtown Louisville, Kentucky.

Jeffersonville
The price is AU$445 per night from 5 Apr to 6 Apr
AU$445
includes taxes & fees
5 Apr - 6 Apr
With a stay at this vacation home in Jeffersonville, you'll be within a 10-minute drive of KFC Yum Center and Kentucky International Convention Center.
Spacious and Beautiful home near downtown Louisville, Kentucky.
3 Bed, 3 Bath Loft in Downtown Louisville! Amazing River Views! Private Deck!

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

Louisville
With a stay at this vacation home in Louisville (Downtown Louisville), you'll be a 3-minute walk from Louisville Slugger Museum and 8 minutes by foot from KFC ...
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!

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

Louisville
The price is AU$1,915 per night from 7 Apr to 8 Apr
AU$1,915
includes taxes & fees
7 Apr - 8 Apr
A stay at this vacation home places you in the heart of Louisville, within a 5-minute drive of Springhurst Towne Center Shopping Center and Paddock Shops.
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
ꕥLuxꕥHeated* Pool/Hot Tub/Gamerooms/Firepit/Outdoor Shower/Bunks

ꕥLuxꕥHeated* Pool/Hot Tub/Gamerooms/Firepit/Outdoor Shower/Bunks

New Albany
With a stay at this vacation home in New Albany, you'll be within a 15-minute drive of KFC Yum Center and Louisville Waterfront Park.
ꕥLuxꕥHeated* Pool/Hot Tub/Gamerooms/Firepit/Outdoor Shower/Bunks
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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.

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
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

Top trending hotels in Charlestown

Radisson Hotel Louisville North

Radisson Hotel Louisville North

3 out of 5
505 Marriott Drive, Clarksville, IN
The price is AU$104 per night from 6 Apr to 7 Apr
AU$104
includes taxes & fees
6 Apr - 7 Apr
When you stay at Radisson Hotel Louisville North in Clarksville, you'll be on a lake, within a 5-minute drive of Louisville Waterfront Park and KFC Yum ...
Radisson Hotel Louisville North
Galt House Hotel Trademark Collection by Wyndham

Galt House Hotel Trademark Collection by Wyndham

4 out of 5
140 North Fourth Street, Louisville, KY
The price is AU$298 per night from 18 Apr to 19 Apr
AU$298
includes taxes & fees
18 Apr - 19 Apr
Galt House Hotel Trademark Collection by Wyndham is in the heart of Louisville, within a 5-minute walk of KFC Yum Center and Kentucky International Convention ...
Galt House Hotel Trademark Collection by Wyndham
Omni Louisville Hotel

Omni Louisville Hotel

4 out of 5
400 S. 2nd Street, Louisville, KY
Fully refundableReserve now, pay when you stay
The price is AU$313 per night from 18 Apr to 19 Apr
AU$313
includes taxes & fees
18 Apr - 19 Apr
With a stay at Omni Louisville Hotel, you'll be centrally located in Louisville, steps from Fourth Street Live! and 4 minutes by foot from Kentucky International ...
Omni Louisville Hotel
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Derby City Gaming & Hotel -  A Churchill Downs Property

Derby City Gaming & Hotel - A Churchill Downs Property

4 out of 5
4520 Poplar Level Rd, Louisville, KY
Fully refundableReserve now, pay when you stay
The price is AU$215 per night from 8 Apr to 9 Apr
AU$215
includes taxes & fees
8 Apr - 9 Apr
When you stay at Derby City Gaming & Hotel - A Churchill Downs Property in Louisville, you'll be near the airport, within a 10-minute drive of Kentucky Exposition ...
Derby City Gaming & Hotel - A Churchill Downs Property
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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.