South Shore Vacations from $392

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Your South Shore Vacation

When you choose a South Shore vacation package, you can kick back and enjoy your escape to the fullest. Uncover the best parts of this fascinating city knowing that everything has been worked out in advance. If sightseeing is a priority during your trip to South Shore, be sure to find your way to well-known attractions like Shawnee State University and Philip Moore Jr. Stone House. Expedia can help you escape the everyday. Tailor your vacation to South Shore to match your travel style, whatever that may be.

The Latest South Shore vacation packages

Price found within the past 48 hours. Click for updated prices.
Knights Inn Ashland
Delta Hotels by Marriott Ashland Downtown
Days Inn by Wyndham Huntington
Holiday Inn Express & Suites Ironton by IHG
DoubleTree by Hilton Huntington
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South Shore Hotel Deals

Fairfield Inn & Suites By Marriott Ashland

Fairfield Inn & Suites By Marriott Ashland

2.5 out of 5
10945 Route 60, Ashland, KY
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $98 total per night from Aug 31 to Sep 1
$98 total
Aug 31 - Sep 1
Total with taxes and fees
8.2/10 Very Good! (679 reviews)
Overnight stay
"The room was clean ,we didn’t see any bugs like some other people said they had. Lady at the front desk was very polite. The breakfast was very good. We’ll be back"

Reviewed on Aug 19, 2025

Fairfield Inn & Suites By Marriott Ashland
Knights Inn Ashland

Knights Inn Ashland

1.5 out of 5
7216 Sr 60, Ashland, KY
$70 nightly
The price is $79 total per night from Aug 25 to Aug 26
$79 total
Aug 25 - Aug 26
Total with taxes and fees
6.8/10 (585 reviews)
"The only thing that I didn't care for was the fact that I was told there would be a pool and there wasn't, but they apologized and said what was wrong, greatly appreciated that"

Reviewed on Aug 9, 2025

Knights Inn Ashland
Carter Caves State Resort Park

Carter Caves State Resort Park

3 out of 5
344 Caveland Dr, Olive Hill, KY
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $95 total per night from Sep 22 to Sep 23
$95 total
Sep 22 - Sep 23
Total with taxes and fees
9/10 Wonderful! (633 reviews)
New Family Getaway Spot
"Amazing and private resort that is kid friendly!"

Reviewed on Aug 19, 2025

Carter Caves State Resort Park
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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Frequently asked questions

How much does a South Shore vacation package cost?
Offering great value package deals from $392 on Expedia, you'll be thrilled with how little a vacation to South Shore costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to South Shore?
January, February and April are great times to search for cheap South Shore vacation packages. Opting to travel in less busy periods means you can generally find lower prices on flights and hotels.
How many days is enough for South Shore?
Generally, a handful of days is enough to explore the top attractions during your South Shore vacation. However, if you'd like to have more time to relax or take day tours, consider extending your trip.
How to find the best South Shore package deals?
Finding a cheap South Shore package deal is a cinch with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget range, apply a couple of filters and see what's available. You can tweak your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most affordable South Shore package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a South Shore vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component individually. And you'll still get the freedom to create a customized South Shore vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to South Shore?
If you're considering a spontaneous South Shore adventure, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can find terrific deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later South Shore vacation packages?
Your South Shore getaway should be a relaxing escape from your busy life, not a reason for money worries. So to allow you a little more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.