South Boston Vacations from $445
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The Latest South Boston Vacation Packages
- Holiday Inn Express Louisville Airport Expo Center by IHG
Jan 13 - Jan 17Holiday Inn Express Louisville Airport Expo Center by IHG + Flight
Hayfield Dundee4 nights2.5 star property8.6/10 - Excellent (1,001 reviews)"Upon entering the property the desk clerk was courteous however I had 2 rooms and they were separated. When walking to the rooms I noticed footprints on the floor and those same footprints were there when I checked out. There appeared to be a permanent ring around the bathtub in one of the rooms and the other room had a bottle top on the floor in a corner. It appears the cleaning staff are not really thorough. I will not return to this location."Reviewed November 5, 2026Roundtrip • Miami (MIA) - Louisville (SDF)MIA - SDF • Nonstop SDF - FLL • Nonstop$561$445found 6 hours agoper traveler - Pillow and Paddock B&B
Dec 11 - Dec 14Pillow and Paddock B&B + Flight
La Grange3 nights3.5 star property10/10 - Exceptional (52 reviews)"Courteous staff and the room was outstanding. It was our second stay at the inn. Everything is first class. We highly recommend it."Reviewed December 22, 2025Roundtrip • Miami (MIA) - Louisville (SDF)FLL - SDF • Nonstop SDF - FLL • Nonstop - The Purple Martin
Dec 11 - Dec 14The Purple Martin + Flight
Prospect3 nights2.0 star property10/10 - Exceptional (2 reviews)"Amazing property… I would come back in a heartbeat! "Reviewed June 19, 2025Roundtrip • Miami (MIA) - Louisville (SDF)FLL - SDF • Nonstop SDF - FLL • Nonstop - Crowne Plaza Louisville Airport Expo Ctr by IHG
Jan 13 - Jan 17Crowne Plaza Louisville Airport Expo Ctr by IHG + Flight
Fairgrounds4 nights3.5 star property8.8/10 - Excellent (1,950 reviews)"I’ve stayed here 5 times for work. Very convenient. The wait staff at the breakfast rush is extremely inconsistent with what is or isn’t included with the breakfast vouchers but that’s likely just due to turn over. Every morning we’ve had someone new."Reviewed November 5, 2026Roundtrip • Miami (MIA) - Louisville (SDF)MIA - SDF • Nonstop SDF - FLL • Nonstop$714$524found 6 hours agoper traveler - Cottonwood Airport & Expo Hotel Louisville
Jan 13 - Jan 17Cottonwood Airport & Expo Hotel Louisville + Flight
Shively4 nights3.5 star property8.8/10 - Excellent (1,002 reviews)Roundtrip • Miami (MIA) - Louisville (SDF)MIA - SDF • Nonstop SDF - FLL • Nonstop$598$454found 6 hours agoper traveler
South Boston Hotel Deals
SureStay by Best Western Salem
SureStay by Best Western Salem
Holiday Inn Express & Suites Scottsburg by IHG
Holiday Inn Express & Suites Scottsburg by IHG
Hampton Inn & Suites Scottsburg
Hampton Inn & Suites Scottsburg"Staff was amazing and very helpful wished the pool was heated but did not effect my overall stay"
"We have stayed at this Knights Inn many times.The property managers have always been very pleasant when checking in.They have always answered any questions we may have."
"We had a very pleasant stay and the owner was very polite. Would definitely come back!"
"I really enjoyed my stay there I will definitely be back if I’m in the area friendly staff excellent service and breakfast quite and peaceful nice place for a little getaway"
Ramada by Wyndham Sellersburg/Louisville North
Ramada by Wyndham Sellersburg/Louisville North"Very clean property, very friendly staff!"
Frequently Asked Questions
How much does a South Boston vacation package cost?
Offering excellent value package deals from $445 on Expedia, you'll be thrilled with how little a vacation to South Boston costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to South Boston?
You're likely to find lower prices and better availability in November, December and January. Take a look at our cheap South Boston vacation packages and you could land some great off-season deals.
How many days is enough for South Boston?
The ideal duration of your South Boston vacation depends on what you'd like to see and do. Generally, a few days to a week will give you enough time to visit all the major sights and discover some hidden gems along the way.
How to find the best South Boston package deals?
Use Expedia's filter tool to help you find some great South Boston package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or search for South Boston package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a South Boston vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking stays and flights individually. Better still, you can personalize your South Boston escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to South Boston?
Land incredible discounts by reserving your flights in advance with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu South Boston getaway.
Does Expedia offer Book Now, Pay Later South Boston vacation packages?
Jet off on your perfect escape to South Boston with help from Expedia's Book Now, Pay Later vacations. No need to save up or hold off until your next paycheck — we've teamed up with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans mean you can split the cost over 3, 6 or 12 months. With no hidden or late payment fees, you can easily budget for your trip and snag great deals while they last.