South Shore Vacations

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  • Better together

    Save up to ₩1,660,000 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place

Find the Best South Shore Vacation Packages

South Shore Hotel Deals

Days Inn by Wyndham Grayson

Days Inn by Wyndham Grayson

2 out of 5
650 CW Stevens Blvd Grayson KY
Fully refundableReserve now, pay when you stay
The price is ₩119,225 per night from Nov 3 to Nov 4
₩119,225
₩131,429 total
Nov 3 - Nov 4
includes taxes & fees
9/10 Wonderful! (463 reviews)
"My daughter and I were doing a college visit and felt so at home at this Days Inn. The staff was so intent on making us feel safe and at home, even asking how the day went. The rooms and bathrooms were SPOTLESS… We will definitely be returning to this place again and again."

Reviewed on Oct 28, 2026

Days Inn by Wyndham Grayson
Delta Hotels by Marriott Ashland Downtown

Delta Hotels by Marriott Ashland Downtown

4 out of 5
1441 Winchester Avenue Ashland KY
Fully refundableReserve now, pay when you stay
The price is ₩159,452 per night from Oct 31 to Nov 1
₩159,452
₩185,921 total
Oct 31 - Nov 1
includes taxes & fees
Delta Hotels by Marriott Ashland Downtown
Greenbo Lake State Resort Park

Greenbo Lake State Resort Park

3 out of 5
965 Lodge Rd Greenup KY
The price is ₩85,681 per night from Nov 5 to Nov 6
₩85,681
₩94,455 total
Nov 5 - Nov 6
includes taxes & fees
Greenbo Lake State Resort Park
See all 163 properties in South Shore
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 Shore vacation package cost?
Offering great value package deals 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?
The off-season is the best time to visit South Shore if you're hoping to keep costs down. Another tip for finding cheap South Shore vacation packages? Try to avoid public holidays and any major festivals or events.
How many days is enough for South Shore?
The ideal length of your South Shore vacation depends on what you'd like to do and see. Generally, a handful of days to a week will give you plenty of time to visit all the leading sights and discover some hidden gems along the way.
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.
How to plan a trip to South Shore?

  1. Choose when to get away: Check your diary and get packing. Your favorite season and the type of activities available will also help you decide when to escape to South Shore.
  2. Budget wisely: In addition to the cost of your stay, you should factor in other expenses. These include food, transportation and flights. Also, put aside a little extra for unexpected expenses that could arise during your trip to South Shore.
  3. Determine how many days away: Start by compiling a list of the attractions you want to experience in South Shore. Then, estimate how long you'll need for each, along with any travel time.
  4. Combine your airfare and accommodations: After you've nailed down your trip dates and duration, lock in the right South Shore vacation package for you.

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