South Boston Vacations from ￥87,651

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The Latest South Boston Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
Fairgrounds
per person
Aug 30 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
8.8/10 Excellent! (637 reviews)
Great experience. Very big and busy hotel but had a great experience. Hotel smelled great. The staff was very friendly and kind. The beds and pillows were so comfy. I would definitely recommend this hotel and I would love to stay here again.

Reviewed on Jul 22, 2025

Louisville Marriott Downtown

Louisville Marriott Downtown

4 out of 5
Downtown Louisville
per person
Aug 30 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
9/10 Wonderful! (1,003 reviews)
Beautiful hotel and excellent service. Location is great too. Will stay at the Marriott when back in Louisville

Reviewed on Jul 5, 2025

The Grady

The Grady

4 out of 5
Downtown Louisville
per person
Aug 30 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
9.4/10 Exceptional! (994 reviews)
Every time I stay in Louisville, I stay at The Grady!

Reviewed on Jul 23, 2025

Hotel Distil, Autograph Collection

Hotel Distil, Autograph Collection

4 out of 5
Downtown Louisville
per person
Aug 30 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
9.6/10 Exceptional! (389 reviews)
Clean, classy with an excellent bar/restaurant!!

Reviewed on Jul 14, 2025

21c Museum Hotel Louisville

21c Museum Hotel Louisville

4.5 out of 5
Downtown Louisville
per person
Aug 30 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
9.2/10 Wonderful! (1,000 reviews)
The staff was great, ver helpful with answering questions about the city. Restaurant had good food and atmosphere. Loved being surrounded by so many wonderful works of art. We would definitely stay again... it's such a vibe.

Reviewed on Jul 20, 2025

Find the Best South Boston Vacation Packages

South Boston Hotel Deals

Ramada by Wyndham Sellersburg/Louisville North

Ramada by Wyndham Sellersburg/Louisville North

2.5 out of 5
360 Triangle Dr, I-65 Exit 9, Sellersburg, IN
Fully refundableReserve now, pay when you stay
The price is ￥11,713 per night from Jul 27 to Jul 28
￥11,713
￥13,235 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
"Great experience and good people"

Reviewed on Jul 18, 2025

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
The price is ￥15,100 per night from Aug 3 to Aug 4
￥15,100
￥16,912 total
Aug 3 - Aug 4
includes taxes & fees
8.6/10 Excellent! (624 reviews)
"As expected."

Reviewed on Jul 15, 2025

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
The price is ￥12,087 per night from Aug 18 to Aug 19
￥12,087
￥13,537 total
Aug 18 - Aug 19
includes taxes & fees
8.4/10 Very Good! (932 reviews)
"Clean friendly staff for most part! Great management! Beds very comfortable nice shower rooms are big overall great place!"

Reviewed on Jul 19, 2025

Hampton Inn & Suites Scottsburg
See all 77 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.

Frequently asked questions

How much does a South Boston vacation package cost?
Offering excellent value package deals from ￥87,651 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 can usually find reduced prices and greater availability in January, February and March. Check out our cheap South Boston vacation packages and you could get some excellent off-season deals.
How many days is enough for South Boston?
Usually, a handful of days is enough to explore the top sights during your South Boston vacation. However, if you prefer to have some time to kick back or go on day tours, think about extending your itinerary.
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.
How to plan a trip to South Boston?

  1. Choose your dates: The things you'd like to do in South Boston and your preferred season will help you decide when to get away.
  2. Set a budget: Consider costs such as flights, food and transportation when working out how much to put aside for your trip to South Boston. Then, select a hotel that matches your budget, whether that's an economical option or a more upscale retreat.
  3. Decide how long to go for: Now that you're more familiar with South Boston, you can figure out the right length of your vacation. Put together a rough plan and allocate enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a customized South Boston vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.