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Charlestown, IN vacation rentals
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Best Vacation rentals and Airbnb offers in Charlestown, IN

Compare Vacation Rentals for Families in Charlestown, IN

These kid-friendly vacation rentals in Charlestown, IN keep you close to top city attractions for a stress-free family vacation.

️Stay At Peppermint Cottage - Norton Commons -Walk Eat & Shop- Free Breakfast - Charlestown, IN
10 158 reviews
Charlestown, IN
08/20 – 08/23
$577/nighttotal: $1731 (3 )

️Stay At Peppermint Cottage - Norton Commons -Walk Eat & Shop- Free Breakfast

3 3
apartment , Prospect
This Prospect vacation rental is conveniently located within two miles of Chamberlain Pointe and Old Brownsboro Crossing shopping centers and Norton Brownsboro Hospital, and within three miles of Paddock Shops and The Summit.
This 1,580-square-foot house features three bedrooms, a fully equipped kitchen with a dishwasher, a private spa, a fitness center, and a relaxing outdoor space with a garden—perfect for families or groups of up to six guests.
Evergreen: Work Friendly & Near Downtown - Charlestown, IN
9.0 32 reviews
Charlestown, IN
08/20 – 08/23
$411/nighttotal: $1233 (3 )

Evergreen: Work Friendly & Near Downtown

3 3
apartment , Jeffersonville
This Jeffersonville vacation home, located within six miles of Clark Memorial Hospital, the Howard Steamboat Museum, Derby Dinner Playhouse, Atlantis Waterpark, and Falls of the Ohio State Park, offers convenient access to major attractions.
This 2,650-square-foot house features four bedrooms, three bathrooms, sleeps ten guests, and includes amenities such as a fully equipped kitchen, free Wi-Fi, a terrace, and barbecue grills.
Watch Hill Manor Bourbon Commons - Charlestown, IN
Charlestown, IN
08/20 – 08/23
$1112/nighttotal: $3336 (3 )

Watch Hill Manor Bourbon Commons

4 3
house , Prospect
Watch Hill Manor Bourbon Commons, a Louisville house rental in Prospect, Kentucky, offers convenient access to attractions like the Muhammad Ali Center, Kentucky Center for the Performing Arts, and Louisville Slugger Museum Factory, all within a 14-mile radius. This 2400-square-foot property boasts two bedrooms, three bathrooms, sleeps up to 15 guests, and includes a private pool, tennis court, and fully equipped kitchen.
King Bed With Backyard Oasis - Charlestown, IN
Charlestown, IN
08/20 – 08/23
$254/nighttotal: $762 (3 )

King Bed With Backyard Oasis

2 3
apartment , New Albany
This 1880s shotgun-style house in New Albany is located 5.9 miles from downtown Louisville and 11 miles from the KY Expo Center.
This pet-friendly rental offers 2 bedrooms and 1 bathroom accommodating up to 4 guests, featuring a hot tub, fire pit, gazebo, and a gourmet-ready kitchen.

Best Charlestown, IN vacation rentals with parking

Townhouse Mins To Uofl & Churchill Downs/hot Tub - Charlestown, IN
9.4 13 reviews
Charlestown, IN
08/20 – 08/23
$194/nighttotal: $582 (3 )

Townhouse Mins To Uofl & Churchill Downs/hot Tub

3 3
apartment , Jeffersonville
This Jeffersonville vacation home boasts a central location, within 3 miles of the Ohio River, the Howard Steamboat Museum, and Clark Memorial Hospital, and within 6 miles of the KFC Yum! Center and Schimpff's Confectionery.
This three-bedroom house comfortably sleeps seven guests and features a fully equipped kitchen with a fridge, microwave, and dishwasher, a Jacuzzi, a patio, free WiFi, and BBQ grills, perfect for families or small groups exploring Jeffersonville's attractions.
Dog-friendly Home W/ Yard, 6 Mi To Louisville! - Charlestown, IN
10 1 review
Charlestown, IN
08/20 – 08/23
$217/nighttotal: $651 (3 )

Dog-friendly Home W/ Yard, 6 Mi To Louisville!

3 3
house , New Albany
This New Albany house rental is conveniently located six miles from downtown Louisville, offering easy access to attractions like the Kentucky Center for the Performing Arts and Louisville International Airport (12 miles away).
The 1400-square-foot home features three bedrooms, two bathrooms, and accommodates up to nine guests, boasting a fenced backyard, fully equipped kitchen, free Wi-Fi, and outdoor dining area.
The Lyric 185 - Norton Commons - Charlestown, IN
10 23 reviews
Charlestown, IN
08/20 – 08/23
$314/nighttotal: $942 (3 )

The Lyric 185 - Norton Commons

2 3
apartment , Prospect
This Prospect apartment rental is conveniently located within three miles of Chamberlain Pointe, Old Brownsboro Crossing, Paddock Shops, Summit Shopping Center, and Norton Brownsboro Hospital.
This 1300-square-foot, three-bedroom, two-bathroom unit sleeps five guests and features a fully equipped kitchen, in-unit laundry, a fireplace, free Wi-Fi, a terrace, and access to a swimming pool, fitness center, and tennis court.
Beach Vibe 2 Miles To Whiskey Row Main Street Louisville Bourbon City Museum Row - Charlestown, IN
10 11 reviews
Charlestown, IN
08/20 – 08/23
$145/nighttotal: $435 (3 )

Beach Vibe 2 Miles To Whiskey Row Main Street Louisville Bourbon City Museum Row

1 3
apartment , Clarksville
This 1-bedroom, 1-bathroom apartment in Clarksville offers a relaxing coastal vibe just 2.7 miles from Downtown Louisville. With a user rating of "excellent," it comfortably accommodates up to 4 guests and provides access to local attractions like the Bourbon Experience and the lively food and entertainment scenes of Jeffersonville and New Albany.
The apartment features a fully equipped kitchen, essential amenities, and a guest host upstairs for assistance. It is pet-friendly and offers internet access for convenience.

Frequently Asked Questions about vacation rentals in Charlestown, IN

  • Which walking or cycling routes are the best in Charlestown, IN?

    The Charlestown State Park has some great trails for both walking and cycling. The Silver Creek Trail is a paved path that goes through the park and is perfect for a leisurely stroll or bike ride. If you're looking for something a little more challenging, the Blue Trail is a 10-mile loop that goes through the woods and along the creek.
  • What are the best Airbnb and vacation rentals in Charlestown, IN?

    Quarry Eight, Charlestown Gem - Whole House Rental and Pet-friendly Emerald Lake Retreat In Charlestown are the most popular Airbnb and vacation rentals in Charlestown, IN among travelers.

  • What sports or outdoor activites can visitors enjoy in and around Charlestown, IN?

    Charlestown is a great place for outdoor activities. You can go hiking, biking, fishing, and kayaking in the Charlestown State Park. The Silver Creek is a popular spot for canoeing and kayaking. If you're looking for something a little more adrenaline-pumping, the nearby Lucas Oil Raceway hosts a variety of racing events throughout the year.
  • What are the most popular Airbnbs in Charlestown, IN?

    Among the Airbnbs in Charlestown, IN, Quarry Eight, Charlestown Gem - Whole House Rental and Test House are the most popular ones.

  • What other towns or cities can be easily accessed from Charlestown, IN?

    Charlestown is conveniently located near Louisville, Kentucky, which is just a short drive away. You can also easily get to New Albany, Indiana, and Jeffersonville, Indiana, both of which are within a 30-minute drive. If you're looking for a day trip, you can even head to Indianapolis, Indiana, which is about a two-hour drive.
  • What are the best rentals for families and kids in Charlestown, IN?

    187 M² House ∙ 4 Bedrooms ∙ 8 Guests and Charlestown 3/2 With Bonus Room -Whole House Rental - Pets Allowed are the best vacation rentals for families and kids in Charlestown, IN.

  • What amenities are commonly available in vacation rentals in Charlestown, IN?

    Vacation rentals in Charlestown typically offer basic amenities like a kitchen, bathroom, and bedrooms. Many also have laundry facilities, a patio or deck, and access to a swimming pool. Some rentals may also have additional features like a hot tub or fireplace.
  • What are the best rentals or Airbnbs with a jacuzzi in Charlestown, IN?

    The best vacation rental or Airbnb with a jacuzzi in Charlestown, IN is Test House.

Destinations nearby

Choose the Right Vacation Rentals with a Terrace in Charlestown, IN

Start your morning right with a vacation rental in Charlestown, IN featuring a private balcony and stunning views.

The Norton Commons Luxe - Charlestown, IN
9.9 100 reviews
Charlestown, IN
08/20 – 08/23
$731/nighttotal: $2193 (3 )

The Norton Commons Luxe

4 3
apartment , Fincastle
This luxurious apartment is located in the Norton Commons neighborhood of Louisville, Kentucky, a short drive from downtown and close to the scenic Ohio River. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
This spacious 5-bedroom home comfortably sleeps 12 guests and offers a large open floor plan with high-end decor. Enjoy a fully equipped kitchen, a basement bar/entertainment area with a pool table and arcade games, a hot tub, and a comfortable outdoor patio.
Park Place Lodge - Stay Play Celebrate - Sleeps 34 - Charlestown, IN
10 7 reviews
Charlestown, IN
08/20 – 08/23
$2933/nighttotal: $8799 (3 )

Park Place Lodge - Stay Play Celebrate - Sleeps 34

9 3
chalet , Jeffersonville
This Jeffersonville lodge is situated near leisure parks, offering a 14-minute walk to the Ohio River and a 5-minute drive to the Big Four Bridge.
This family-friendly chalet boasts 10,000 square feet of space, accommodating up to 34 guests with 10 bedrooms and 9 bathrooms, and features a fully equipped kitchen, complimentary Wi-Fi, and an on-site fitness center.
Unique Riverfront Gaffney Lux Home! Scenic Views - Charlestown, IN
10 1 review
Charlestown, IN
08/20 – 08/23
$986/nighttotal: $2958 (3 )

Unique Riverfront Gaffney Lux Home! Scenic Views

4 3
apartment , Glenview
This historic estate is located in Louisville's Glenview Estates neighborhood, offering direct Ohio River waterfront access and is a short drive from downtown Louisville attractions, including Churchill Downs and distilleries.
This 5010 square foot house features four king bedrooms with ensuite bathrooms, gourmet kitchens, expansive terraces, and includes full access to the Louisville Thoroughbred Society Members-Only club for up to 8 guests.
Family Resort Home With Heated Pool And Games - Charlestown, IN
Charlestown, IN
08/20 – 08/23
$1266/nighttotal: $3798 (3 )

Family Resort Home With Heated Pool And Games

5 3
apartment , Jeffersonville
This spacious 5-bedroom, 4-bathroom Jeffersonville vacation home offers exclusive access to a fenced backyard with a heated saltwater pool and pool house, located just 10 miles from downtown Louisville attractions like the KFC Yum Center and the Louisville Slugger Museum, and within 5 miles of theme parks such as Kentucky Kingdom and the Louisville Zoo. This 3220 square foot residence accommodates up to 20 guests with amenities including a full kitchen, air conditioning, and parking, while offering opportunities for outdoor adventures like hiking and boating in the surrounding area.

Discover Pet-Friendly Vacation Rentals in Charlestown, IN

Experience a pet-friendly stay in Charlestown, IN with vacation rentals located steps away from city dog parks and walking trails.

Charming House, Sleeps Plenty With Hot Tub And Large Backyard And Fire Pit - Charlestown, IN
9.6 5 reviews
Charlestown, IN
08/20 – 08/23
$289/nighttotal: $867 (3 )

Charming House, Sleeps Plenty With Hot Tub And Large Backyard And Fire Pit

2 3
apartment , Jeffersonville
This Jeffersonville house rental is conveniently located a 4-minute drive from the Ohio River and a 5-minute drive from the Big Four Bridge, offering easy access to downtown Louisville attractions.
This two-bedroom, one-bathroom home sleeps seven guests and features a fully equipped kitchen with microwave, washer/dryer, a Jacuzzi, and a relaxing outdoor space with a patio and hot tub; free Wi-Fi is also included.
3807 Hamburg Pike,new Home 2025, Perfect For A Family ,With A Jacuzzi Hot Tub, - Charlestown, IN
10 7 reviews
Charlestown, IN
08/20 – 08/23
$295/nighttotal: $885 (3 )

3807 Hamburg Pike,new Home 2025, Perfect For A Family ,With A Jacuzzi Hot Tub,

3 3
apartment , Jeffersonville
This Jeffersonville apartment rental is conveniently located near the Kentucky Exposition Center (a 15-minute drive) and the KFC Yum! Center (an 8-minute drive), offering easy access to major Louisville attractions.
This three-bedroom, two-bathroom unit sleeps six guests and boasts a fully equipped kitchen, in-unit laundry, a Jacuzzi, and a private terrace—all within a pet-friendly setting with on-site parking and grilling facilities.
Equus: Work Friendly & Near Downtown - Charlestown, IN
9.0 6 reviews
Charlestown, IN
08/20 – 08/23
$354/nighttotal: $1062 (3 )

Equus: Work Friendly & Near Downtown

3 3
apartment , Jeffersonville
This Jeffersonville vacation home is conveniently located within 6 miles of Kentuckiana Medical Center and Clark Memorial Hospital, and within 9 miles of Louisville attractions such as the KFC Yum Center and the Howard Steamboat Museum.
This 1,320-square-foot house features three bedrooms, two bathrooms, and accommodates up to six guests, offering free Wi-Fi, in-house laundry, and a fully equipped kitchen with a refrigerator, microwave, dishwasher, oven, and stovetop.
The Pilots Pad - Charlestown, IN
9.9 56 reviews
Charlestown, IN
08/20 – 08/23
$215/nighttotal: $645 (3 )

The Pilots Pad

2 3
apartment , Sellersburg
The Pilots Pad is a charming farmhouse located in Clarksville, Indiana, just minutes from Sellersburg and a short drive from Louisville, Kentucky. This accommodation consistently receives excellent ratings for its cleanliness, location, and overall experience.
The Pilots Pad is a two-bedroom home with a daybed and trundle in the game room, comfortably sleeping six guests. The farmhouse features a fully equipped kitchen, a relaxing garden, and a game room equipped with ping pong and board games, perfect for family fun.
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