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Our top choices for Charlestown vacation homes

Emerald Lake Retreat Charlestown

Charlestown
10.0 out of 10, Exceptional, (3)
"This a great place for families to gather. It's very spacious and clean and comfortable. And though it's in a quiet and peaceful area with a small lake at the base of the property, places to eat and get groceries are just a short drive away. There's a wonderful seating area around a firepit, too!"
United States
Kelly P.
The price is AED 422
AED 1,656 total
includes taxes & fees
12 Dec - 13 Dec
Emerald Lake Retreat Charlestown

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

Charlestown
10.0 out of 10, Exceptional, (12)
"The property was clean and quiet. Great location in a nice residential neighborhood. Very close to Charlestown State Park where we did some hiking."
United States
Chris S.
The price is AED 349
AED 540 total
includes taxes & fees
10 Dec - 11 Dec
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE

Pendleton
9.8 out of 10, Exceptional, (62)
"Came to the area for a funeral. Worked out great for our needs. Alecia was quick to respond any time we called. Enjoyed it. "
United Kingdom
Clyde C.
The price is AED 323
AED 858 total
includes taxes & fees
13 Dec - 14 Dec
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE

New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!

South Louisville
10.0 out of 10, Exceptional, (22)
"We were just passing through, it was perfect place our family of five. We were looking for something besides a hotel and the price was so reasonable. Owner was very nice!"
United States
Carla H.
The price is AED 151
AED 644 total
includes taxes & fees
15 Dec - 16 Dec
New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!

Cozy home in St. Matthews, 2 bedrooms, 2 bathrooms

St. Matthews
9.0 out of 10, Wonderful, (6)
"Stayed for a friends wedding at Whitehall. Location was great and we were able to walk to a handful of restaurants and coffee shops "
United States
Natalie H.
The price is AED 281
AED 978 total
includes taxes & fees
10 Dec - 11 Dec
Cozy home in St. Matthews, 2 bedrooms, 2 bathrooms

Modern Nature Cabin | Private Escape in the Forest

Hanover
9.8 out of 10, Exceptional, (7)
"Very nice facility and relaxing setting . "
United States
Robert V.
The price is AED 381
AED 880 total
includes taxes & fees
23 Dec - 24 Dec
Modern Nature Cabin | Private Escape in the Forest

Lumos Stays: 65" 4K TV, memory foam, kid-friendly

Bon Air
10.0 out of 10, Exceptional, (5)
"This was a very pleasant and comfortable stay at this home! I thoroughly enjoyed the decor, and everything was clean and well-maintained. Overall, it was a great stay."
United States
Brionna W.
The price is AED 403
AED 1,201 total
includes taxes & fees
16 Dec - 17 Dec
Lumos Stays: 65" 4K TV, memory foam, kid-friendly

Private Home Close to Zoo, U of L, Churchill Downs

Poplar Level
9.6 out of 10, Exceptional, (19)
"I love this property! Great neighborhood near the park and zoo, comfortable beds, and a nice living room to hang out in. Very charming older home"
United States
Rosemary P.
The price is AED 290
AED 1,103 total
includes taxes & fees
10 Dec - 11 Dec
Private Home Close to Zoo, U of L, Churchill Downs

The Burnt Barrel | New HotTub & Grill | Backyard!

2.0 star property
Germantown
10.0 out of 10, Exceptional, (1)
"Excellent walking to different little shops. Super decorated inside and out. Loved the hot tub. Would stay again! "
United States
kevin m.
The price is AED 363
AED 851 total
includes taxes & fees
10 Dec - 11 Dec
The Burnt Barrel | New HotTub & Grill | Backyard!

Stylish House Walking Distance from the Fun of the Highlands!

Phoenix Hill
9.6 out of 10, Exceptional, (24)
"We enjoyed our stay. The place was just as advertised. The host was so helpful and easy to reach. "
United States
Trena D.
The price is AED 312
AED 801 total
includes taxes & fees
10 Dec - 11 Dec
Stylish House Walking Distance from the Fun of the Highlands!

Southern Family Charmer - Perfect Space & Location with style and comfort!

Schnitzelburg
10.0 out of 10, Exceptional, (22)
"We had a great stay in Louisville. The property was beautiful, and location was perfect. "
United States
Kelsea Y.
The price is AED 343
AED 1,059 total
includes taxes & fees
10 Dec - 11 Dec
Southern Family Charmer - Perfect Space & Location with style and comfort!

Close to Everything in Louisville!!!

Camp Taylor
9.4 out of 10, Exceptional, (37)
"Matches the description and photos "
United States
Angela C.
The price is AED 349
AED 946 total
includes taxes & fees
10 Dec - 11 Dec
Close to Everything in Louisville!!!

Fam & Business Stay | Cozy Home in Prime Location!

2.0 star property
Smoketown Jackson
10.0 out of 10, Exceptional, (2)
"Great location for our stay while attending the state fair. Fit all of us perfectly. Beautifully remodeled 20th century home. Host was amazing. "
United States
Le Ann G.
The price is AED 275
AED 823 total
includes taxes & fees
10 Dec - 11 Dec
Fam & Business Stay | Cozy Home in Prime Location!

⭐Fully fenced yard⭐4 car driveway⭐firepit⭐central location⭐basement⭐

Avondale Melbourne Heights
9.6 out of 10, Exceptional, (49)
"Great home with plenty of bedrooms and beds. "
United States
Megan D.
The price is AED 459
AED 1,445 total
includes taxes & fees
16 Dec - 17 Dec
⭐Fully fenced yard⭐4 car driveway⭐firepit⭐central location⭐basement⭐

The Rose & Pine Cottage in Phoenix Hill

Phoenix Hill
8.8 out of 10, Excellent, (18)
"Place was clean, the neighborhood was ok, good communication with host."
United States
Teresa B.
The price is AED 227
AED 732 total
includes taxes & fees
17 Dec - 18 Dec
The Rose & Pine Cottage in Phoenix Hill

Charming 3BR Home | Near Louisville Attractions!

2.0 star property
South Louisville
10.0 out of 10, Exceptional, (1)
"House was clean with all appliances functioning well. Host was responsive. The property was described well. The location was ideal for a visit to Churchill Downs or to attend a Louisville football game. "
United States
Claude M.
The price is AED 389
AED 963 total
includes taxes & fees
15 Dec - 16 Dec
Charming 3BR Home | Near Louisville Attractions!

Stylish Jeffersonville Home - Mins from Louisville

Jeffersonville
9.0 out of 10, Wonderful, (20)
"This was a great place for us to stay for an event at the expedition center. Close to the highway for quick access to the city. "
United States
Chad L.
The price is AED 289
AED 1,161 total
includes taxes & fees
7 Jan - 8 January 2026
Stylish Jeffersonville Home - Mins from Louisville

Carriage House, 7 minutes from downtown Louisville

louisville
10.0 out of 10, Exceptional, (46)
"Located near lovely parks on the river. There is very little traffic in this area, yet you are close to downtown.We've stayed here twice because it is so clean, comfortable, stylish, and relaxing. "
United States
Debbie B.
The price is AED 496
AED 887 total
includes taxes & fees
10 Dec - 11 Dec
Carriage House, 7 minutes from downtown Louisville

Cozy Home | Walk to Churchill & Cardinal Stadium!

2.0 star property
Wilder Park
10.0 out of 10, Exceptional, (1)
"The property had 3 nice size bedrooms and 1-1/2 baths with a modern kitchen and nice layout. I appreciated the quiet neighborhood and off road parking."
United States
Lise M.
The price is AED 363
AED 970 total
includes taxes & fees
15 Dec - 16 Dec
Cozy Home | Walk to Churchill & Cardinal Stadium!

Steps to Restaurants, Nightlife, Shops- PacMan/King Bed/Bardstown Rd/Highlands

Louisville
10.0 out of 10, Exceptional, (10)
"My family of four (boys 9 and 11) were in town for a week to visit family. Great stay, clean place, wonderfully helpful and responsive owner. "
United States
Matthew B.
Steps to Restaurants, Nightlife, Shops- PacMan/King Bed/Bardstown Rd/Highlands
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