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
Stay at this vacation home in Louisville. Enjoy free WiFi, a garden, and patios. Popular attractions Churchill Downs and Fourth Street Live! are located ...
Charming shotgun home, in the heart of Louisville!
Enchanting, energizing, and enjoyable!

Enchanting, energizing, and enjoyable!

Buckner
Stay at this vacation home in Buckner. Enjoy a fitness center, a garden, and a pool table. Popular attractions Open Range Sports and Yew Dell Botanical Gardens ...
Enchanting, energizing, and enjoyable!
The Curated Chateau—Minutes from Louisville

The Curated Chateau—Minutes from Louisville

New Albany
Book a stay at this family-friendly vacation home in New Albany. Enjoy free WiFi, a water park, and patios. Popular attractions Louisville Slugger Museum and ...
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
Stay at this vacation home in Louisville. Enjoy air conditioning. Popular attractions Fourth Street Live! and KFC Yum Center are located nearby.
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
Stay at this vacation home in New Albany. Enjoy free WiFi, a garden, and patios. Popular attractions Louisville Slugger Museum and KFC Yum Center are located ...
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 NZ$485 per night from 3 Apr to 4 Apr
NZ$485
includes taxes & fees
3 Apr - 4 Apr
Stay at this vacation home in Jeffersonville. Enjoy air conditioning. Popular attractions Louisville Waterfront Park and KFC Yum Center are located nearby.
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
Stay at this vacation home in Louisville. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Louisville Slugger Museum and KFC Yum ...
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 NZ$2,099 per night from 7 Apr to 8 Apr
NZ$2,099
includes taxes & fees
7 Apr - 8 Apr
Book a stay at this family-friendly vacation home in Louisville. Enjoy free WiFi, a water park, and a fitness center. Popular attractions Springhurst Towne Center ...
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
Stay at this vacation home in New Albany. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Louisville Slugger Museum and KFC Yum Center ...
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
961 Holiday Homes
Lowest Price
NZ$115
Highest Price
NZ$2,099
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
Fully refundableReserve now, pay when you stay
The price is NZ$115 per night from 3 Apr to 4 Apr
NZ$115
includes taxes & fees
3 Apr - 4 Apr
Stay at this 3-star business-friendly hotel in Clarksville. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the clean rooms and the overall ...
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 NZ$330 per night from 18 Apr to 19 Apr
NZ$330
includes taxes & fees
18 Apr - 19 Apr
Book a stay at this spa hotel in Louisville. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the restaurant and the helpful staff in ...
Galt House Hotel Trademark Collection by Wyndham
Omni Louisville Hotel

Omni Louisville Hotel

4 out of 5
400 S. 2nd Street, Louisville, KY
The price is NZ$347 per night from 18 Apr to 19 Apr
NZ$347
includes taxes & fees
18 Apr - 19 Apr
Stay at this 4-star spa hotel in Louisville. Enjoy a full-service spa, 3 restaurants, and 3 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
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 NZ$239 per night from 8 Apr to 9 Apr
NZ$239
includes taxes & fees
8 Apr - 9 Apr
Stay at this 4-star hotel in Louisville. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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.