Charlestown Vacation Packages
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Your Charlestown Vacation
From its rich history to its coastal scenery and beyond, there's loads to love about Charlestown. Discover the wonders of this fascinating city with a Charlestown vacation package that's tailor-made for you. If visiting the sights is a must during your trip to Charlestown, make sure you stop by well-known attractions like Charlestown State Park and Charlestown Family Activities Park. Expedia is here to help you escape your daily routine. Tailor your vacation to Charlestown to suit your travel style, whatever that may be.
Top Charlestown Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Louisville Mall of St. Matthews
St. Matthews
Price was CA $1,390, price is now CA $1,097 per person
CA $1,097
per person
Mar 18 - Mar 24
found 6 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Louisville (SDF)
9.4/10 Exceptional! (835 reviews)
Room was spotless, amenities was up to date, and the location was perfect....... Will be booking here again!
Reviewed on Feb 1, 2026
Louisville Marriott Downtown
Downtown Louisville
Price was CA $2,073, price is now CA $1,479 per person
CA $1,479
per person
Mar 18 - Mar 24
found 6 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Louisville (SDF)
9/10 Wonderful! (1,003 reviews)
Room was spotless. Staff was top notch. Amenities as expected but I did expect a microwave in the room. There wasn't one. 9/10 experience. Will definitely book again!
Reviewed on Jan 16, 2026
Galt House Hotel Trademark Collection by Wyndham
Downtown Louisville
Price was CA $1,734, price is now CA $1,308 per person
CA $1,308
per person
Mar 18 - Mar 24
found 6 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Louisville (SDF)
9/10 Wonderful! (3,770 reviews)
Nice room, comfortable bed, large fridge for a hotel.room.
Reviewed on Feb 8, 2026
The Grady
Downtown Louisville
Price was CA $2,163, price is now CA $1,661 per person
CA $1,661
per person
Mar 18 - Mar 24
found 6 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Louisville (SDF)
9.4/10 Exceptional! (1,001 reviews)
Property was very well taken care of and unique. Staff was friendly and helpful. Room was very nice and the price was great!
Reviewed on Feb 3, 2026
Derby City Gaming & Hotel - A Churchill Downs Property
Price was CA $5,891, price is now CA $4,695 per person
CA $4,695
per person
Apr 30 - May 3
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Louisville (SDF)
9.4/10 Exceptional! (1,606 reviews)
Beautiful room, beautiful atmosphere. Staff was wonderful.
Reviewed on Feb 7, 2026
Charlestown Hotel Deals
Galt House Hotel Trademark Collection by Wyndham
140 North Fourth Street Louisville KY
Fully refundableReserve now, pay when you stay
The price is CA $213 per night from Feb 17 to Feb 18
CA $213
CA $251 total
Feb 17 - Feb 18
includes taxes & fees
8.8/10 Excellent! (4,047 reviews)
Overall good experience. The renovated rooms are so much nicer than the previous rooms. The Galt House is in a great location and parking is easy-in, easy-out. On the unfortunate side for us: the bedroom in our executive suite was very cold and the beds were uncomfortable with loud, rustling thin ...
Reviewed on Feb 7, 2026
Omni Louisville Hotel
400 S. 2nd Street Louisville KY
Fully refundableReserve now, pay when you stay
The price is CA $283 per night from Feb 9 to Feb 10
CA $283
CA $333 total
Feb 9 - Feb 10
includes taxes & fees
9.2/10 Wonderful! (1,777 reviews)
All good
Reviewed on Feb 5, 2026
Radisson Hotel Louisville North
505 Marriott Drive Clarksville IN
Fully refundableReserve now, pay when you stay
The price is CA $81 per night from Mar 11 to Mar 12
CA $81
CA $91 total
Mar 11 - Mar 12
includes taxes & fees
6.8/10 (2,769 reviews)
Everything in the room worked everything was clean and spotless the staff was very sweet especially Miss Jenny thank you Ms Jenny the pool was clean although it was a little cold but that was just because the ceiling fan was on and it's kind of an open pool but we enjoyed every moment. We will be ...
Reviewed on Feb 1, 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
