South Boston Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to CA $1,096 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top South Boston Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Louisville Airport
Fairgrounds
Price was CA $1,000, price is now CA $691 per person
CA $691
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
9/10 Wonderful! (1,001 reviews)
Nice spacious rooms with comfy beds. Not a lot of food options for breakfast
Reviewed on Aug. 10, 2025
Crowne Plaza Louisville Airport Expo Ctr by IHG
Fairgrounds
Price was CA $1,036, price is now CA $747 per person
CA $747
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.8/10 Excellent! (795 reviews)
Second time staying here. Staff is helpful, parking is good, room was clean and comfortable. Easy access to get around town.
Reviewed on Sep. 1, 2025
Galt House Hotel Trademark Collection by Wyndham
Downtown Louisville
Price was CA $1,067, price is now CA $791 per person
CA $791
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
9/10 Wonderful! (3,563 reviews)
When staying at the Galt House, it is all about the location. The hotel is much bigger than I realized and would be an ideal place for a large convention. It is right at the heart of everything there is to do in Louisville and comes with a decent view of the Ohio River. We had a perfectly nice night at the Galt House and the price was very respectable. I wouldn't call it one of Louisville's "best" hotels, but it is definitely in the upper tier. We would definitely consider staying again.
Reviewed on Sep. 4, 2025
Homewood Suites by Hilton Louisville-East
Price was CA $941, price is now CA $745 per person
CA $745
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
9.6/10 Exceptional! (634 reviews)
We thoroughly enjoyed our stay at the Homewood Suites Louisville-East. The hotel was nice, clean and quiet and the staff were welcoming and friendly. Our room was a nice size and the bed was very comfortable. I would highly recommend.
Reviewed on Sep. 1, 2025
Embassy Suites Louisville Downtown
Downtown Louisville
Price was CA $992, price is now CA $785 per person
CA $785
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
9/10 Wonderful! (1,017 reviews)
Every person I came in contact with during my stay way excellent. The greatest staff ever.
I’ll be back for sure.
Reviewed on Sep. 3, 2025
South Boston Hotel Deals
Holiday Inn Express & Suites Scottsburg by IHG
200 S Beechwood Ave, Scottsburg, IN
Fully refundable
The price is CA $157 per night from Sep 7 to Sep 8
CA $157
CA $176 total
Sep 7 - Sep 8
includes taxes & fees
Ramada by Wyndham Sellersburg/Louisville North
360 Triangle Dr, I-65 Exit 9, Sellersburg, IN
Fully refundableReserve now, pay when you stay
The price is CA $110 per night from Sep 7 to Sep 8
CA $110
CA $125 total
Sep 7 - Sep 8
includes taxes & fees
Hampton Inn & Suites Scottsburg
1535 W Mcclain Ave, Scottsburg, IN
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from Sep 29 to Sep 30
CA $148
CA $165 total
Sep 29 - Sep 30
includes taxes & fees
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.
Other vacations you might like
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
