Photo by Mark Wilcoxson

Holiday Homes in Charlestown

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
12 Sept - 14 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov
In four months
19 Dec - 21 Dec

Featured Holiday Homes in Charlestown

Our top choices for Charlestown holiday homes

Bourbon Trail Retreat 5 King Beds Sleeps 18 Gated Private Family-Friendly
Microwave, oven, stovetop, dishwasher

Bourbon Trail Retreat 5 King Beds Sleeps 18 Gated Private Family-Friendly

10.0 out of 10, Exceptional, (1)
"This post will be long. My family and I were completely surprised by the beauty of this property. The intentionality of the bedrooms, interior decorations, the size of the property , so we all could stretch out. I am thoroughly impressed. We will be back."
Bourbon Trail Retreat 5 King Beds Sleeps 18 Gated Private Family-Friendly
✪Heated Pool, Firepit, Bikes, Grill, Pets✪
Fridge, microwave, oven, stovetop

✪Heated Pool, Firepit, Bikes, Grill, Pets✪

8.6 out of 10, Excellent, (17)
"Thank you for sharing your lovely home with us. The pool was a hit with the kids and we had a wonderful time relaxing and enjoying our vacation. Thank you for being such gracious hosts and providing us with a comfortable and enjoyable stay. We hope to visit again in the future!"
The price is AU$571
includes taxes & fees
15 Sept - 16 Sept
✪Heated Pool, Firepit, Bikes, Grill, Pets✪
Close to Everything in Louisville!!!
Exterior detail

Close to Everything in Louisville!!!

9.4 out of 10, Exceptional, (33)
"Very clean and nice place close to the exposition center would stay there again."
The price is AU$429
includes taxes & fees
10 Sept - 11 Sept
Close to Everything in Louisville!!!
Stay on Broadway - Sleeps 10, Hot Tub, Walkable!
Exterior

Stay on Broadway - Sleeps 10, Hot Tub, Walkable!

9.0 out of 10, Wonderful, (7)
"Visit to celebrate my wife’s commencement, we all enjoyed our stay very much"
Stay on Broadway - Sleeps 10, Hot Tub, Walkable!
Spectacular waterfront house!
Outdoor spa tub

Spectacular waterfront house!

9.6 out of 10, Exceptional, (78)
"We had a great time and loved the view of the river! "
Spectacular waterfront house!
Relaxing Country Getaway
Interior

Relaxing Country Getaway

9.4 out of 10, Exceptional, (36)
"Wonderful stay, very private. Cozy place perfect for couples looking to unwind. Would stay again."
Relaxing Country Getaway
The Caldwell - Germantown Highlands
Fridge, microwave, oven, stovetop

The Caldwell - Germantown Highlands

10.0 out of 10, Exceptional, (30)
"Nice house for our weekend stay. We would book again! "
The price is AU$298
includes taxes & fees
10 Sept - 11 Sept
The Caldwell - Germantown Highlands
New! The Old Timer - 5BR/4.5BA - Hot Tub! Historic!
TV, table football, offices

New! The Old Timer - 5BR/4.5BA - Hot Tub! Historic!

9.4 out of 10, Exceptional, (30)
"Great location and awesome place to stay. We all had a great time!"
New! The Old Timer - 5BR/4.5BA - Hot Tub! Historic!
Louisville's Best Area, Walk to All!
Exterior

Louisville's Best Area, Walk to All!

9.8 out of 10, Exceptional, (177)
"A beautiful, well maintained and clean home. The owners were responsive, friendly and helpful. I would absolutely stay here again."
Louisville's Best Area, Walk to All!
Family Friendly, Historic Mansion Row, **5 min from Louisville!**
Lobby

Family Friendly, Historic Mansion Row, **5 min from Louisville!**

10.0 out of 10, Exceptional, (39)
"Convent and accommodation was excellent for 10 "
Family Friendly, Historic Mansion Row, **5 min from Louisville!**
☆Stunning Derby Home☆ 5 KING BEDS, HOT TUB,FIREPIT
Fridge, coffee/tea maker, cookware/dishes/utensils

☆Stunning Derby Home☆ 5 KING BEDS, HOT TUB,FIREPIT

9.0 out of 10, Wonderful, (33)
"Relaxing, fun time with family. Back yard is a treasure. "
The price is AU$607
includes taxes & fees
2 Sept - 3 Sept
☆Stunning Derby Home☆ 5 KING BEDS, HOT TUB,FIREPIT
Parklike Estate in the Heart of Louisville w/Pool and Gardens -- Family Friendly
Fridge, microwave, oven, stovetop

Parklike Estate in the Heart of Louisville w/Pool and Gardens -- Family Friendly

10.0 out of 10, Exceptional, (137)
"The property is fabulous! Our group absolutely loved the stay. we liked the property so much that we found ourselves cutting our visits throughout Kentucky short to get back to the house to enjoy the accommodation. "
Parklike Estate in the Heart of Louisville w/Pool and Gardens -- Family Friendly
Germantown - Perfect for Groups
Fridge, microwave, oven, stovetop

Germantown - Perfect for Groups

9.8 out of 10, Exceptional, (18)
"Home met our needs for a long weekend trip with 4 adults. Beds were all comfortable and neighborhood is quiet and central. Didn't meet "excellent" expectation due to several cosmetic repairs that are needed."
Germantown - Perfect for Groups
Historic District Townhouse in City's BEST Location
Fridge, microwave, oven, stovetop

Historic District Townhouse in City's BEST Location

9.8 out of 10, Exceptional, (198)
"Would definitely stay again, very ideal location for visiting Louisville. "
Historic District Townhouse in City's BEST Location
3-story Bourbon Luxe Historic Retreat 2 mi to Whiskey Row-NULU
4 bedrooms, desk, iron/ironing board, travel cot

3-story Bourbon Luxe Historic Retreat 2 mi to Whiskey Row-NULU

10.0 out of 10, Exceptional, (81)
"House is gorgeous. Proximity to downtown is great. Owners were very communicative and helpful. Can’t find anything bad to say at all. "
3-story Bourbon Luxe Historic Retreat 2 mi to Whiskey Row-NULU
Wanderlust - Hot tub / fire pit - Location!
Outdoor spa tub

Wanderlust - Hot tub / fire pit - Location!

9.8 out of 10, Exceptional, (7)
"4 guys in our group. We all had big comfy beds and enjoyed the hot tub and fire pit outside. Would recommend!"
Wanderlust - Hot tub / fire pit - Location!
Charming home in the heart of the city!
Terrace/patio

Charming home in the heart of the city!

9.8 out of 10, Exceptional, (9)
"Cozy house with modern updates & a great location. House is bigger on the inside than it looks and was able to accommodate all of us. The owner communicated everything in a timely matter and made sure everything was smooth. Would stay here again!"
The price is AU$486
includes taxes & fees
10 Sept - 11 Sept
Charming home in the heart of the city!
The Bonnycastle Massive 6BR New Orleans Themed Speakeasy, Bourbon Game Room & Hot Tub & Playground
Exterior

The Bonnycastle Massive 6BR New Orleans Themed Speakeasy, Bourbon Game Room & Hot Tub & Playground

10.0 out of 10, Exceptional, (27)
"We had the house for a wedding weekend in Louisville. The location was great, one block walk to Bardstown Road. We were three couples and had more than enough space. We had no complaints and would stay again. "
The Bonnycastle Massive 6BR New Orleans Themed Speakeasy, Bourbon Game Room & Hot Tub & Playground
Cozy Cottage on Spring---Centrally Located and 10 mins from downtown Louisville
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (40)
"We were in the Louisville area for our daughter’s graduation. This home worked out great for our stay. We would stay here again in the future."
The price is AU$597
includes taxes & fees
8 Sept - 9 Sept
Cozy Cottage on Spring---Centrally Located and 10 mins from downtown Louisville
The Riverside Retreat - Your Coastal Getaway
Terrace/patio

The Riverside Retreat - Your Coastal Getaway

9.6 out of 10, Exceptional, (48)
"This is a great place to say that is very quiet and peaceful! Perfect for a weekend getaway!"
The Riverside Retreat - Your Coastal Getaway
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Charlestown Hotel Reviews

Find out more about Charlestown

Find out more about Charlestown

Charlestown Holiday Homes information

Number of reviews
272
Accommodation
977 Holiday Homes
Lowest Price
AU$298
Highest Price
AU$607

Explore a world of travel with Expedia

Explore a world of travel with Expedia