Photo by Mark Wilcoxson

Search Vacation Homes in Charlestown

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 21 - Nov 23
In two months
Jan 2 - Jan 4
In three months
Jan 30 - Feb 1
In four months
Feb 27 - Mar 1

Vacation Homes in Charlestown

Fridge, microwave, oven, stovetop
Emerald Lake Retreat Charlestown
Emerald Lake Retreat Charlestown
10.0 out of 10, Exceptional, (3)
"Roomy, clean, nice setting in nice neighborhood."
United States
David P.
$405 nightly
The price is $458
Nov 8 - Nov 9
Total with taxes and fees
Emerald Lake Retreat Charlestown
Interior
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
10.0 out of 10, Exceptional, (11)
"We enjoyed the spacious rooms, quick access to local restaurants and how well equipped the space was. Our host Tiffinie was super responsive and helpful. The entry stairs were a little challenging after a full day of exploring but manageable. The apartment was located on a historical block with cool old houses Next-door. Overall a really terrific stay!"
United States
Shelly D.
$130 nightly
The price is $147
Nov 9 - Nov 10
Total with taxes and fees
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Fridge, microwave, oven, stovetop
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
9.8 out of 10, Exceptional, (59)
"My husband and I enjoyed this sweet country retreat. The peaceful setting encouraged much relaxation and long conversations. Perfect weekend."
United States
Rita G.
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
Fridge, microwave, oven, stovetop
Modern Nature Cabin | Private Escape in the Forest
Modern Nature Cabin | Private Escape in the Forest
9.8 out of 10, Exceptional, (7)
"Every thing was very nice!"
United States
Tom F.
$200 nightly
The price is $211
Nov 11 - Nov 12
Total with taxes and fees
Modern Nature Cabin | Private Escape in the Forest
Fridge, microwave, oven, stovetop
New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!
New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!
10.0 out of 10, Exceptional, (22)
"Clean fantastic property, great communication, easy walk to Churchill Downs!"
United States
Benjamin W.
$179 nightly
The price is $208
Nov 9 - Nov 10
Total with taxes and fees
New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!
Exterior
Cozy home in St. Matthews, 2 bedrooms, 2 bathrooms
Cozy home in St. Matthews, 2 bedrooms, 2 bathrooms
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.
$211 nightly
The price is $245
Nov 9 - Nov 10
Total with taxes and fees
Cozy home in St. Matthews, 2 bedrooms, 2 bathrooms
Private kitchen
Putt Putt House by Louisville Walking Bridge
Putt Putt House by Louisville Walking Bridge
2.0 star property
10.0 out of 10, Exceptional, (9)
"We stayed for 3 days while our granddaughter was in a basketball tournament. It worked out great for us, we had no problems at all. Clean, convenient and close to everything. If we come back next year we’ll try to stay there again."
United States
Ron R.
$260 nightly
The price is $294
Nov 11 - Nov 12
Total with taxes and fees
Putt Putt House by Louisville Walking Bridge
Terrace/patio
The Chestnut - Nulu
The Chestnut - Nulu
2.0 star property
9.8 out of 10, Exceptional, (25)
"Had a great time"
United States
Tracey Y.
$166 nightly
The price is $193
Nov 9 - Nov 10
Total with taxes and fees
The Chestnut - Nulu
5 bedrooms, internet
5BR Very Spacious Home! Perfect for Family!
5BR Very Spacious Home! Perfect for Family!
9.2 out of 10, Wonderful, (18)
"My company stayed here during a work trip and we liked it so much we extended our stay. Great area with lots to do!"
United States
Kalvin W.
$411 nightly
The price is $428
Nov 10 - Nov 11
Total with taxes and fees
5BR Very Spacious Home! Perfect for Family!
TV
Charming Home w Fenced Backyard and Free Parking
Charming Home w Fenced Backyard and Free Parking
2.0 star property
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.
$264 nightly
The price is $281
Nov 9 - Nov 10
Total with taxes and fees
Charming Home w Fenced Backyard and Free Parking
Exterior detail
Close to Everything in Louisville!!!
Close to Everything in Louisville!!!
9.4 out of 10, Exceptional, (36)
"Very clean and nice place close to the exposition center would stay there again."
United States
jaggers959
$218 nightly
The price is $253
Nov 10 - Nov 11
Total with taxes and fees
Close to Everything in Louisville!!!
Exterior
Cozy Home | Walk to Churchill & Cardinal Stadium!
Cozy Home | Walk to Churchill & Cardinal Stadium!
2.0 star property
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.
$270 nightly
The price is $287
Nov 9 - Nov 10
Total with taxes and fees
Cozy Home | Walk to Churchill & Cardinal Stadium!
Exterior
Cozy Tiny House in Scottsburg
Cozy Tiny House in Scottsburg
10.0 out of 10, Exceptional, (1)
"Cute, clean, and comfortable stay! Great communication with host! "
United States
Teresa B.
$151 nightly
The price is $169
Nov 15 - Nov 16
Total with taxes and fees
Cozy Tiny House in Scottsburg
Fridge, microwave, oven, stovetop
Quiet Upper Highlands 1 Block to Bardstown Road
Quiet Upper Highlands 1 Block to Bardstown Road
10.0 out of 10, Exceptional, (36)
"Beautiful home, great hosts, easy access to everything "
United States
Tracy L.
$319 nightly
The price is $366
Nov 18 - Nov 19
Total with taxes and fees
Quiet Upper Highlands 1 Block to Bardstown Road
Terrace/patio
DerbyCity Getaway | Hot Tub | Near Churchill Downs
DerbyCity Getaway | Hot Tub | Near Churchill Downs
8.4 out of 10, Very Good, (6)
"Awesome place to stay! Kind of a sketchy neighborhood but the place makes up for itself. Tall fence surrounding the backyard where you can park your car, locked gate as well. In the back is a very nice lounging area with a beautiful kind of glow in the dark mural, and then you can’t get any better than a hot tub. Thanks for the awesome stay!"
United States
Joshua R.
$170 nightly
The price is $189
Dec 2 - Dec 3
Total with taxes and fees
DerbyCity Getaway | Hot Tub | Near Churchill Downs
Outdoor dining
Charming house in one of Louisville's most coveted neighborhoods
Charming house in one of Louisville's most coveted neighborhoods
10.0 out of 10, Exceptional, (76)
"Really enjoyed our time in Louisville and at this VRBO."
United States
Alyssa S.
$247 nightly
The price is $286
Nov 11 - Nov 12
Total with taxes and fees
Charming house in one of Louisville's most coveted neighborhoods
Fridge, microwave, oven, stovetop
Close to Expo Ctr, UofL, Walk to bars, shops!
Close to Expo Ctr, UofL, Walk to bars, shops!
10.0 out of 10, Exceptional, (68)
"Lovely property in a nice neighborhood that reminded us of Soulard in STL"
United States
Emily B.
$166 nightly
The price is $192
Nov 9 - Nov 10
Total with taxes and fees
Close to Expo Ctr, UofL, Walk to bars, shops!
Game room
Prime Location | Spacious 3-BR First Floor Unit!
Prime Location | Spacious 3-BR First Floor Unit!
2.0 star property
8.0 out of 10, Very Good, (1)
"Excellent property, quiet and enjoyable"
United States
Blane W.
$234 nightly
The price is $249
Nov 10 - Nov 11
Total with taxes and fees
Prime Location | Spacious 3-BR First Floor Unit!
Fridge, microwave, oven, stovetop
Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.
Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.
10.0 out of 10, Exceptional, (31)
"Easy check in. Very clean. Attentive host. Will definitely rent again. "
United States
Lenor M.
$175 nightly
The price is $198
Dec 1 - Dec 2
Total with taxes and fees
Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.
Fridge, microwave, oven, stovetop
Walk to EVERYTHING! Steps to Restaurants/Shopping/Nightlife! ~Bardstown Rd /4ppl
Walk to EVERYTHING! Steps to Restaurants/Shopping/Nightlife! ~Bardstown Rd /4ppl
10.0 out of 10, Exceptional, (3)
"This was a great jumping off point for our adventures around Louisville!"
United States
Allison M.
$169 nightly
The price is $196
Nov 9 - Nov 10
Total with taxes and fees
Walk to EVERYTHING! Steps to Restaurants/Shopping/Nightlife! ~Bardstown Rd /4ppl
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.
View all properties
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

Holiday Inn Express & Suites Louisville Downtown by IHG

Holiday Inn Express & Suites Louisville Downtown by IHG

10/10 Excellent
"The front staff was amazing, so helpful and accommodating. The room was clean"
Lisa 2-night trip
Posted 1 day ago
Holiday Inn Express & Suites Louisville Downtown by IHG

Find out more about Charlestown

Charlestown Vacation Homes information

Number of reviews
407
Accommodation
930 Vacation Homes
Lowest Price
$147
Highest Price
$458

Explore a world of travel with Expedia