South Boston Vacations from $348
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The Latest South Boston vacation packages
Price found within the past 48 hours. Click for updated prices.
The Brown Hotel
Downtown Louisville
$365
per person
Oct 23 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Louisville (SDF)
9.4/10 Exceptional! (1,289 reviews)
Got there late. Will say that the front desk staff was nice and check in and bar was nice enough to give us silverware for our leftovers. We did need to request a fridge to our room, but staff was super nice about it and brought it quickly with no extra charge. I thought the room would be bigger though. Room was small. Didn't feel luxurious, felt like just a bedroom in my home. Nothing special. Bed was TERRIBLE. Super hard bed. Felt like I was sleeping on a rod. A sofa pull out couch might have been better. No room service menu provided. Last time I stayed you were able to put a breakfast room request form on the door for the next morning. That was a bummer. Bathroom was nice though. Probably a one and done stay. The room really wasn't worth the price.
Reviewed on Sep 18, 2026
The Trail Hotel
$607
per person
Oct 23 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Louisville (SDF)
9.2/10 Wonderful! (318 reviews)
This was advertised as a HOTEL….. this is MOST DEFINITELY NOT A HOTEL. This is a glorified motel- did not appreciate the accommodation situation, lack of ease to access our room, size of room, layout of room was a typical motel. Did not like at all!
This is false advertising when it’s offered as a Hotel and when you show up to find out it’s a motel, but the reservation is non refundable.
Reviewed on Sep 18, 2026
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Ramada by Wyndham Sellersburg/Louisville North
360 Triangle Dr Sellersburg IN
Fully refundableReserve now, pay when you stay
$84 nightly
$95 total
Sep 21 - Sep 22
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
"Overall not bad, clean and quiet. Disappointing that at price you pay you have to join the rewards program to get free internet or pay almost $5 to use it."
Reviewed on Sep 18, 2026
Holiday Inn Express & Suites Scottsburg by IHG
200 S Beechwood Ave Scottsburg IN
Fully refundable
$102 nightly
$114 total
Oct 18 - Oct 19
Total with taxes and fees
HavenPointe Inn & Suites
300 N Gardner St Scottsburg IN
$82 nightly
$91 total
Sep 21 - Sep 22
Total with taxes and fees
8.8/10 Excellent! (666 reviews)
"This is a freshly remodeled facility that is very clean. The staff was excellent also. I would highly recommend this property to anyone."
Reviewed on Sep 14, 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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South Boston Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Louisville Intl. Airport (SDF) |
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Frequently asked questions
How much does a South Boston vacation package cost?
Offering excellent value package deals from $348 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.