Charlestown Vacation Rentals

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Our top choices for Charlestown vacation rentals

Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Charlestown
10.0 out of 10, Exceptional, (17 reviews)
"House was cozy, and host was responsive. Rooms were clean and welcoming. A lovely place to stay."
United States
Alec S.
The price is CA $149
CA $223 total
includes taxes & fees
Jun 2 - Jun 3
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

Emerald Lake Retreat Charlestown

Emerald Lake Retreat Charlestown
Charlestown
10.0 out of 10, Exceptional, (3 reviews)
"Roomy, clean, nice setting in nice neighborhood."
United States
David P.
The price is CA $178
CA $649 total
includes taxes & fees
May 10 - May 11
Emerald Lake Retreat Charlestown

Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance

Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance
Louisville
9.8 out of 10, Exceptional, (144 reviews)
"Very nice couple , will stay there again"
United States
Bryan S.
The price is CA $348
CA $554 total
includes taxes & fees
May 26 - May 27
Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance

Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!

Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!
Jeffersontown
9.6 out of 10, Exceptional, (32 reviews)
"We had a wonderful experience. The house was great and had everything we needed. Everything was clean and well maintained. The host was very friendly, responsive, and flexible, which we really appreciated. Would definitely stay again!"
United States
Dieudonne N.
The price is CA $491
CA $1,015 total
includes taxes & fees
May 10 - May 11
Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!

Historic stone cabin near Bourbon Trail on private 13 acre estate property!

Historic stone cabin near Bourbon Trail on private 13 acre estate property!
Louisville
10.0 out of 10, Exceptional, (20 reviews)
"Everything was outstanding!"
United States
John W.
The price is CA $244
CA $388 total
includes taxes & fees
May 13 - May 14
Historic stone cabin near Bourbon Trail on private 13 acre estate property!

3.7 Acre Estate w/ Heated Pool, 5 Kings-2 Game Rms

3.7 Acre Estate w/ Heated Pool, 5 Kings-2 Game Rms
La Grange
10.0 out of 10, Exceptional, (21 reviews)
"We had a wonderful stay!"
United States
Katie H.
The price is CA $338
CA $1,224 total
includes taxes & fees
May 17 - May 18
3.7 Acre Estate w/ Heated Pool, 5 Kings-2 Game Rms

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
9.8 out of 10, Exceptional, (80 reviews)
"We brought a large group to a conference in Louisville and it was perfect to have all of us stay together. It was a historic house, full of charm. Only negative was the warm water ran out quickly with so many people."
United States
Benjamin T.
The price is CA $876
CA $1,705 total
includes taxes & fees
May 11 - May 12
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!

Charming house in one of Louisville's most coveted neighborhoods NO CLEANING FEE

Charming house in one of Louisville's most coveted neighborhoods NO CLEANING FEE
Louisville
10.0 out of 10, Exceptional, (82 reviews)
"Host was accommodating and welcoming. "
United States
Bobbie S.
The price is CA $259
CA $343 total
includes taxes & fees
May 12 - May 13
Charming house in one of Louisville's most coveted neighborhoods NO CLEANING FEE

Charming 3BR w Large Yard Walk to Downtown

Charming 3BR w Large Yard Walk to Downtown
Jeffersonville
9.6 out of 10, Exceptional, (29 reviews)
"We enjoyed our stay"
United States
Jennifer L.
The price is CA $316
CA $782 total
includes taxes & fees
May 10 - May 11
Charming 3BR w Large Yard Walk to Downtown

Stunning Victorian Home - prime location minutes from Louisville

Stunning Victorian Home - prime location minutes from Louisville
Jeffersonville
9.8 out of 10, Exceptional, (27 reviews)
"We really enjoyed our stay. Close to everything!"
United States
cheryl n.
The price is CA $314
CA $803 total
includes taxes & fees
May 17 - May 18
Stunning Victorian Home - prime location minutes from Louisville

Victorian Center Jeffersonville

Victorian Center Jeffersonville
Jeff
9.4 out of 10, Exceptional, (54 reviews)
"House was beautiful! We were in town for the Kentucky Derby, so everything was higher than normal, but this house was still reasonable compared to others. Location was great! Nice neighborhood within walking distance to restaurants and the river. Very peaceful and not at all concerned with safety. The upstairs suite was huge! Tons of room and everything we needed."
United States
Randi
The price is CA $265
CA $483 total
includes taxes & fees
May 11 - May 12
Victorian Center Jeffersonville

A Cozy Cottage Near the Heart of All Louisville Attractions!

A Cozy Cottage Near the Heart of All Louisville Attractions!
Cloverleaf
10.0 out of 10, Exceptional, (390 reviews)
"Wonderful little place to stay for a weekend. 10/10 recommend staying here. Quiet and serene, and the hosts have thought of everything- very nicely equipped!"
United States
Amanda E.
The price is CA $197
CA $262 total
includes taxes & fees
May 12 - May 13
A Cozy Cottage Near the Heart of All Louisville Attractions!

Cozy Cottage on Spring---Centrally Located and 10 mins from downtown Louisville

Cozy Cottage on Spring---Centrally Located and 10 mins from downtown Louisville
New Albany
10.0 out of 10, Exceptional, (56 reviews)
"This house was perfect and Molly is an exceptional host! "
United States
Julie T.
The price is CA $277
CA $579 total
includes taxes & fees
May 11 - May 12
Cozy Cottage on Spring---Centrally Located and 10 mins from downtown Louisville

Carriage House, 7 minutes from downtown Louisville

Carriage House, 7 minutes from downtown Louisville
louisville
10.0 out of 10, Exceptional, (56 reviews)
"Amazing host! Great place to stay."
United States
Robert M.
The price is CA $185
CA $333 total
includes taxes & fees
May 10 - May 11
Carriage House, 7 minutes from downtown Louisville

Spectacular waterfront house!

Spectacular waterfront house!
Prospect
9.6 out of 10, Exceptional, (92 reviews)
"The home was great, the host was very responsive."
United States
jasmine p.
The price is CA $376
CA $767 total
includes taxes & fees
Jun 9 - Jun 10
Spectacular waterfront house!

Great Location-5 Bd/3 Ba-Near Expo/UL/Fair/YUM/Zoo

Great Location-5 Bd/3 Ba-Near Expo/UL/Fair/YUM/Zoo
Louisville
10.0 out of 10, Exceptional, (8 reviews)
"We had a great stay. House was as advertised, clean, and great location. Would stay again."
United States
Robert T.
The price is CA $447
CA $831 total
includes taxes & fees
Jun 8 - Jun 9
Great Location-5 Bd/3 Ba-Near Expo/UL/Fair/YUM/Zoo

Uptown Class

Uptown Class
New Albany
10.0 out of 10, Exceptional, (18 reviews)
"Great property. Good location. "
United States
Damont P.
The price is CA $171
CA $571 total
includes taxes & fees
May 10 - May 11
Uptown Class

Chestnut Street Charmer-Walk to Louisville!

Chestnut Street Charmer-Walk to Louisville!
Jeffersonville
10.0 out of 10, Exceptional, (15 reviews)
"The house was clean and spacious. A great place to stay while in town for a family gathering."
United States
Connie D.
The price is CA $205
CA $448 total
includes taxes & fees
May 10 - May 11
Chestnut Street Charmer-Walk to Louisville!

Near Highways and a 20 Min Drive to Louisville's Main Attractions

Near Highways and a 20 Min Drive to Louisville's Main Attractions
Louisville
10.0 out of 10, Exceptional, (53 reviews)
"Great place!"
United States
Nakoma F.
The price is CA $234
CA $537 total
includes taxes & fees
May 17 - May 18
Near Highways and a 20 Min Drive to Louisville's Main Attractions

Urban Explorer Pad | Near Downtown + Yard

Urban Explorer Pad | Near Downtown + Yard
Jeffersonville
9.0 out of 10, Wonderful, (43 reviews)
"Amazing stay, would stay again any time! Host was easy to communicate with and home was clean when we arrived and had everything needed for a wonderful stay!"
United States
Cameron J.
The price is CA $249
CA $467 total
includes taxes & fees
May 10 - May 11
Urban Explorer Pad | Near Downtown + Yard
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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Top Charlestown Hotel Reviews

Find out more about Charlestown

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Charlestown. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Charlestown?

Yes, we give you a choice of vacation rentals in Charlestown close to Charlestown Family Activities Park, or you can choose a more remote option if you'd like a relaxing place to stay. Charlestown is known for its riverfront.

What are some of the best vacation home rentals that Charlestown has to offer?

Newly renovated 4BR CozySuites: This vacation home rental outside Charlestown is equipped with a garden, air-conditioning, and free WiFi to help you feel comfortable during your stay. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Charlestown?

With 5 Expedia vacation rentals, you're sure to find just the right place for your Charlestown stay.

What can I see and do in Charlestown?

Ohio River Valley and Woodford Farms Family Park are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Charlestown Family Activities Park. Other places in town to visit include Charlestown State Park and Rose Island.

What are vacation rentals like in Charlestown?

Vacation rentals are private properties you can stay in for a short or long stay in Charlestown. Vacation rentals feature amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a family trip or a small group gathering.