South Boston Vacation Packages
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Top South Boston Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Grady
Downtown Louisville
CA $850
per person
Nov 27 - Nov 30
found 16 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Louisville (SDF)
9.4/10 Exceptional! (1,008 reviews)
Very thin walls; I could hear the folks next door talking. There is no iron or ironing board in the room; you need to request one from the front desk. The front desk was very helpful in getting it to me.
Reviewed on Oct 1, 2026
The Duke Hotel
Downtown Louisville
CA $865
per person
Nov 27 - Nov 30
found 16 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Louisville (SDF)
8.2/10 Very good! (23 reviews)
Check in was difficult because there are two separate buildings and I was not given a room number or door code or instructions about which building I was supposed to be in.
The hotel spammed my email with literally 18 messages most of which were redundant and others which had links that didn’t work.
The actual room was fine and in a nice area. Unfortunately for me, my particular room was directly above a bar that played loud thumping music past 2:30 in the morning on a Monday. I asked the bar if they would turn it down but they didn’t care and acted like I was crazy for asking. I couldn’t sleep. They should never put guests in this room.
Parking is included but you have to register with the adjacent lot which requires you pay a fee which will be refunded eventually. They didn’t refund my fee and actually charged me an additional fee which I didn’t authorize. It took a lot of time and patience to get them to refund both charges.
This place ruined my stay in Louisville, and further troubled me after I got home. I think Expedia should take them off their listing. 0/10.
Reviewed on Sep 19, 2026
Ready to book your vacation to South Boston?
South Boston Hotel Deals
Ramada by Wyndham Sellersburg/Louisville North
360 Triangle Dr Sellersburg IN
Fully refundableReserve now, pay when you stay
CA $121
CA $137 total
Nov 2 - Nov 3
includes taxes & fees
Holiday Inn Express & Suites Scottsburg by IHG
200 S Beechwood Ave Scottsburg IN
Fully refundable
CA $155
CA $174 total
Oct 25 - Oct 26
includes taxes & fees
8.8/10 Excellent! (739 reviews)
"In the hallway that goes to the rooms on the floor, I stayed on black mold was growing all over the ceiling. Only one elevator was working out of 3 during the sold out concert that was sat right next to the hotel."
Reviewed on Sep 29, 2026
HavenPointe Inn & Suites
300 N Gardner St Scottsburg IN
CA $102
CA $118 total
Oct 4 - Oct 5
includes taxes & fees
8.8/10 Excellent! (676 reviews)
"The shower could use handrails as the floor seemed slick. We put a towel down on the shower floor and everything was fine."
Reviewed on Oct 2, 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.
Frequently asked questions
How much does a South Boston vacation package cost?
You can snap up a vacation package to this popular destination from CA $777 on Expedia. But how much your vacation to South Boston costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to South Boston?
If you're hoping to score a cheap South Boston vacation package, consider visiting in January, February and March. You'll generally find lower prices on hotels and flights during these months — ideal for a budget-friendly break.
How many days is enough for South Boston?
The ideal length of your South Boston vacation depends on what you'd like to see and do. Typically, a few days to a week will give you enough time to check out all the top sights and explore some hidden spots along the way.
How to find the best South Boston package deals?
Start your search for a South Boston package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select some filters, like "Popular locations" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal South Boston package deal right away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your South Boston getaway off to a flying start.
Is it cheaper to book a South Boston vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component separately. And you'll still enjoy the flexibility to create a customized South Boston vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to South Boston?
If you've got your South Boston travel dates locked in, book as soon as you can to snap up some incredible deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to South Boston?
- Choose when to go: Check your calendar and get your bags packed. Your preferred season and the activities on offer will also help you decide when to vacation in South Boston.
- Figure out your budget: Ensure you have enough money to cover everything from meals and transportation to activities and airfares. Your accommodations will probably be the largest expense during your trip to South Boston.
- Decide how long to go away for: Now that you're more familiar with South Boston, you can work out the ideal length of your vacation. Pull together a draft plan and allocate enough time to get through everything on your must-do list.
- Combine your accommodations and airfare: Once you've settled on your trip dates and duration, lock in the right South Boston vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
