South Boston Vacations from $467

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The Latest South Boston vacation packages

Price found within the past 48 hours. Click for updated prices.
Louisville Marriott Downtown

Louisville Marriott Downtown

4 out of 5
Downtown Louisville
Price was $600, price is now $467 per person
$467
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
9/10 Wonderful! (1,005 reviews)
clean facility and rooms staff

Reviewed on May 10, 2026

Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

3.5 out of 5
Shively
Price was $676, price is now $494 per person
$494
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
8.6/10 Excellent! (1,011 reviews)
Front desk was super. The breakfast was good. It was noisy but it was Kentucky derby week.

Reviewed on May 12, 2026

Holiday Inn Louisville Airport South by IHG

Holiday Inn Louisville Airport South by IHG

3 out of 5
Price was $888, price is now $668 per person
$668
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
8.8/10 Excellent! (882 reviews)
The room was clean and the staff was wonderful

Reviewed on May 11, 2026

Hotel Distil, Autograph Collection

Hotel Distil, Autograph Collection

4 out of 5
Downtown Louisville
Price was $661, price is now $533 per person
$533
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
9.6/10 Exceptional! (465 reviews)
Love staying here when we are in Louisville.

Reviewed on May 2, 2026

Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
Fairgrounds
Price was $1,040, price is now $844 per person
$844
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
8.8/10 Excellent! (1,366 reviews)
Very clean room. The staff was very polite checking in and out. Hotel was perfect for my one night stay.

Reviewed on May 13, 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
$78 nightly
The price is $88 total per night from May 19 to May 20
$88 total
May 19 - May 20
Total with taxes and fees
8.4/10 Very Good! (1,008 reviews)
Had a fantastic stay at this location. Front desk attendant was very professional, room was spacious and clean, shower had great water pressure and temperature. I would be happy to stay here again.

Reviewed on May 6, 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
$116 nightly
The price is $130 total per night from May 25 to May 26
$130 total
May 25 - May 26
Total with taxes and fees
8.8/10 Excellent! (695 reviews)
Everything was very comfortable. Would suggest this location to any one

Reviewed on May 8, 2026

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

Travelodge by Wyndham Sellersburg / Louisville North

2 out of 5
7618 Old State Road 60 Sellersburg IN
6.8/10 (727 reviews)
Great place, Great location !! Owner and staff are awesome. Breakfast could be a bit better, but it was ok. Very nice stay and very affordable !!

Reviewed on May 11, 2026

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Travelodge by Wyndham Sellersburg / Louisville North
See all 79 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 $467 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.