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Charlestown Vacation Packages

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Charlestown Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
Price was $685, price is now $559 per person
$559
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Louisville (SDF)
Book a stay at this business-friendly hotel in Louisville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Kentucky Kingdom and L&N Federal Credit Union Stadium are located nearby.
Good price close to airport. Parking was hard to find.

Reviewed on Sep 15, 2026

The Reserve on Main

The Reserve on Main

4 out of 5
Save 100% on your flight
Price was $4,442, price is now $3,488 per person
$3,488
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Louisville (SDF)
Stay at this aparthotel in Louisville. Enjoy free WiFi, onsite spa services, and cable TV channels. Popular attractions Louisville Slugger Museum and KFC Yum Center are located nearby.

Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

3.5 out of 5
Price was $899, price is now $719 per person
$719
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
Book a stay at this business-friendly hotel in Louisville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Churchill Downs and L&N Federal Credit Union Stadium are located nearby.
The room was clean, bed was comfortable. The staff at the desk was friendly. My only complaint was that one elevator was down. We were on the fifth floor and the hotel was very busy for Labor Day weekend so we ended up using the stairs a lot. It seems to me that there should be a service elevator as well as two guest elevators.

Reviewed on Sep 14, 2026

Hotel Distil, Autograph Collection

Hotel Distil, Autograph Collection

4 out of 5
Price was $920, price is now $749 per person
$749
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Houston (IAH) to Louisville (SDF)
Book a stay at this business-friendly hotel in Louisville. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions KFC Yum Center and Louisville Slugger Museum are located nearby.

The Purple Martin

The Purple Martin

2 out of 5
Price was $1,023, price is now $833 per person
$833
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Louisville (SDF)
Book a stay at this golf hotel in Prospect. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Chamberlain Pointe Shopping Center and Old Brownsboro Crossing Shopping Center are located nearby.
Amazing property… I would come back in a heartbeat!

Reviewed on Jun 19, 2025

Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Price was $872, price is now $712 per person
$712
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
Book a stay at this business-friendly hotel in Louisville. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions KFC Yum Center and Louisville Slugger Museum are located nearby.

The Grady

The Grady

4 out of 5
Price was $877, price is now $717 per person
$717
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
Stay at this hotel in Louisville. Enjoy free WiFi, breakfast (surcharge), and valet parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Louisville Slugger Museum and KFC Yum Center are located nearby.

Louisville Marriott Downtown

Louisville Marriott Downtown

4 out of 5
Price was $960, price is now $789 per person
$789
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
Book a stay at this business-friendly hotel in Louisville. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions KFC Yum Center and Whiskey Row are located nearby.
The staff was amazing and the hotel was very nice and clean however, the biggest issues was the hotel was incredibly hot everywhere! The ladies restrooms were like saunas and it was difficult to maintain a decent temperature. The hotel really needs to address the temperature issues.

Reviewed on Sep 14, 2026

Charlestown Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

3.5 out of 5
Shively
Price was $899, price is now $719 per person
$719
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
Moxy Louisville Downtown

Moxy Louisville Downtown

3.5 out of 5
Downtown Louisville
Price was $1,010, price is now $809 per person
$809
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Louisville (SDF)
Hotel Distil, Autograph Collection

Hotel Distil, Autograph Collection

4 out of 5
Downtown Louisville
Price was $920, price is now $749 per person
$749
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Houston (IAH) to Louisville (SDF)
The Purple Martin

The Purple Martin

2 out of 5
Price was $1,023, price is now $833 per person
$833
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Louisville (SDF)

Charlestown Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Brown Hotel

The Brown Hotel

4.5 out of 5
Downtown Louisville
Price was $819, price is now $631 per person
$631
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Louisville (SDF)
The Grady

The Grady

4 out of 5
Downtown Louisville
Price was $921, price is now $690 per person
$690
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Louisville (SDF)
Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Downtown Louisville
Price was $847, price is now $644 per person
$644
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Louisville (SDF)
stayAPT Suites Louisville North-Clarksville

stayAPT Suites Louisville North-Clarksville

4 out of 5
Price was $856, price is now $664 per person
$664
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Louisville (SDF)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Breeze Airways
Thu, Nov 12 - Sun, Nov 15
TPA
Tampa Intl.
SDF
Louisville Intl.
$203 Roundtrip, found 22 hours ago
$203
Roundtrip
found 22 hours ago
Select Breeze Airways flight, departing Thu, Nov 12 from Tampa Intl. to Louisville Intl., returning Sun, Nov 15, priced at $203 found 22 hours ago
Southwest Airlines
Tue, Oct 6 - Wed, Oct 14
LGA
LaGuardia
SDF
Louisville Intl.
$209 Roundtrip, found 21 hours ago
$209
Roundtrip
found 21 hours ago
Select Southwest Airlines flight, departing Tue, Oct 6 from LaGuardia to Louisville Intl., returning Wed, Oct 14, priced at $209 found 21 hours ago
Bargain Flight
Thu, Nov 19 - Tue, Dec 8
MSP
Minneapolis - St. Paul Intl.
SDF
Louisville Intl.
$233 Roundtrip, found 21 hours ago
$233
Roundtrip
found 21 hours ago
Select Bargain Flight flight, departing Thu, Nov 19 from Minneapolis - St. Paul Intl. to Louisville Intl., returning Tue, Dec 8, priced at $233 found 21 hours ago
Bargain Flight
Mon, Nov 23 - Tue, Dec 8
DFW
Dallas-Fort Worth Intl.
SDF
Louisville Intl.
$253 Roundtrip, found 5 days ago
$253
Roundtrip
found 5 days ago
Select Bargain Flight flight, departing Mon, Nov 23 from Dallas-Fort Worth Intl. to Louisville Intl., returning Tue, Dec 8, priced at $253 found 5 days ago