South Boston Vacations from $753

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The Latest South Boston vacation packages

Price found within the past 48 hours. Click for updated prices.
Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

3.5 out of 5
Shively
Price was $1,000, price is now $753 per person
$753
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
8.6/10 Excellent! (1,007 reviews)

The Purple Martin

The Purple Martin

2 out of 5
Price was $1,071, price is now $814 per person
$814
per person
Sep 19 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Louisville (SDF)
10/10 Exceptional! (2 reviews)
Amazing property… I would come back in a heartbeat!

Reviewed on Jun 19, 2025

The Grady

The Grady

4 out of 5
Downtown Louisville
Price was $1,550, price is now $1,182 per person
$1,182
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Louisville (SDF)
9.4/10 Exceptional! (1,015 reviews)

Galt House Hotel Trademark Collection by Wyndham

Galt House Hotel Trademark Collection by Wyndham

4 out of 5
Downtown Louisville
Price was $1,037, price is now $838 per person
$838
per person
Oct 20 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Louisville (SDF)
9/10 Wonderful! (4,213 reviews)
We liked the convenience to the KFC Yum Center, but were disappointed with the cleanliness. Our whole floor and room smelled bad. Skittles on the floor in our room. No in room instructions on how to operate the atypical hvac thermostat (had to call for assistance) or television (normal operational buttons didn’t even work). No information in room about on site amenities, restaurants, etc. so we had to keep bothering the staff with basic questions. The staff were responsive and helpful, but overall quality of hotel was less than we were expecting.

Reviewed on Aug 4, 2026

Moxy Louisville Downtown

Moxy Louisville Downtown

3.5 out of 5
Downtown Louisville
Price was $1,122, price is now $911 per person
$911
per person
Sep 23 - Sep 26
found 20 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
9.2/10 Wonderful! (805 reviews)
Man, honestly, it’s clean. They just don’t have anything like zero amenities.

Reviewed on Aug 2, 2026

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South Boston Hotel Deals

Ramada by Wyndham Sellersburg/Louisville North

Ramada by Wyndham Sellersburg/Louisville North

2.5 out of 5
360 Triangle Dr Sellersburg IN
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $95 total per night from Aug 6 to Aug 7
$95 total
Aug 6 - Aug 7
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
"Everything was great. All the normal things. Good size breakfast area. Would stay there again if in the area."

Reviewed on Aug 2, 2026

Ramada by Wyndham Sellersburg/Louisville North
Holiday Inn Express & Suites Scottsburg by IHG

Holiday Inn Express & Suites Scottsburg by IHG

2.5 out of 5
200 S Beechwood Ave Scottsburg IN
Fully refundable
$117 nightly
The price is $131 total per night from Aug 22 to Aug 23
$131 total
Aug 22 - Aug 23
Total with taxes and fees
Holiday Inn Express & Suites Scottsburg by IHG
Hampton Inn & Suites Scottsburg

Hampton Inn & Suites Scottsburg

2.5 out of 5
1535 W Mcclain Ave Scottsburg IN
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $127 total per night from Aug 10 to Aug 11
$127 total
Aug 10 - Aug 11
Total with taxes and fees
Hampton Inn & Suites Scottsburg
See all 82 properties in South Boston
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.

Find the Best South Boston Vacation Packages

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 $753 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.