Search Deals onCharlestown Vacation Packages
Charlestown Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Caesars Southern Indiana Hotel & Casino - A Caesars Rewards Destination
Price was $856, price is now $761 per person
$761
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
Book a stay at this spa hotel in Elizabeth. Enjoy free parking, a full-service spa, and 3 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Horseshoe Southern Indiana Casino and Waverly Hills Sanatorium are located nearby.
Louisville Marriott Downtown
Price was $1,131, price is now $985 per person
$985
per person
Nov 29 - Dec 2
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.
Didn’t like the many homeless people right outside on the sidewalk.
Reviewed on Oct 1, 2026
Hotel Distil, Autograph Collection
Price was $1,235, price is now $1,088 per person
$1,088
per person
Nov 29 - Dec 2
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, a rooftop terrace, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Whiskey Row and KFC Yum Center are located nearby.
Great hotel, right in the middle of the city.
Reviewed on Sep 27, 2026
The Brown Hotel
Price was $975, price is now $871 per person
$871
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
Book a stay at this luxury 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 Whiskey Row are located nearby.
The Grady
Price was $1,100, price is now $990 per person
$990
per person
Nov 29 - Dec 2
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.
Great place to stay in downtown Louisville. Staff is always friendly and helpful.
Reviewed on Oct 2, 2026
Pillow and Paddock B&B
Price was $1,482, price is now $1,353 per person
$1,353
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
Stay at this B&B in La Grange. Enjoy free WiFi, breakfast (surcharge), and onsite spa services. Popular attractions Lagrange Quarry and Walsh Park are located nearby.
Courteous staff and the room was outstanding. It was our second stay at the inn. Everything is first class. We highly recommend it.
Reviewed on Dec 22, 2025
Cottonwood Airport & Expo Hotel Louisville
Price was $896, price is now $818 per person
$818
per person
Nov 29 - Dec 2
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.
Friendly staff, clean lobby and room was big and comfortable.
Reviewed on Oct 2, 2026
Moxy Louisville Downtown
Price was $971, price is now $889 per person
$889
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
Book a stay at this family-friendly hotel in Louisville. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Whiskey Row and KFC Yum Center are located nearby.
Charlestown Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Charlestown Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Thu, Nov 5 - Thu, Nov 19
TPA
Tampa Intl.
SDF
Louisville Intl.
$168 Roundtrip, found 21 hours ago
$168
Roundtrip
found 21 hours ago
Mon, Dec 7 - Wed, Dec 9
MSP
Minneapolis - St. Paul Intl.
SDF
Louisville Intl.
$220 Roundtrip, found 1 day ago
$220
Roundtrip
found 1 day ago
Mon, Nov 23 - Tue, Dec 8
DFW
Dallas-Fort Worth Intl.
SDF
Louisville Intl.
$270 Roundtrip, found 4 days ago
$270
Roundtrip
found 4 days ago
Tue, Nov 3 - Sat, Nov 14
BOS
Logan Intl.
SDF
Louisville Intl.
$277 Roundtrip, found 4 days ago
$277
Roundtrip
found 4 days ago
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