South Shore Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

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.

Ready to book your vacation to South Shore?

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South Shore Hotel Deals

Days Inn by Wyndham Grayson

Days Inn by Wyndham Grayson

650 CW Stevens Blvd Grayson KY
Fully refundableReserve now, pay when you stay
CA $127
CA $140 total
Oct 11 - Oct 12
includes taxes & fees
9/10 Wonderful! (449 reviews)
"This is my regular place to stay when traveling to Illinois. Kathy at the front desk always makes me feel like I am coming home. Rooms are always clean and cozy."

Reviewed on Oct 7, 2026

Days Inn by Wyndham Grayson
Delta Hotels by Marriott Ashland Downtown

Delta Hotels by Marriott Ashland Downtown

1441 Winchester Avenue Ashland KY
Fully refundableReserve now, pay when you stay
CA $188
CA $219 total
Nov 1 - Nov 2
includes taxes & fees
Delta Hotels by Marriott Ashland Downtown
Greenbo Lake State Resort Park

Greenbo Lake State Resort Park

965 Lodge Rd Greenup KY
CA $91
CA $101 total
Oct 29 - Oct 30
includes taxes & fees
Greenbo Lake State Resort Park
See all 162 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations
Golf Vacations
Golf Vacations
Luxury Vacations
Luxury Vacations
Romantic Vacations
Romantic Vacations
Ski Vacations
Ski Vacations

Frequently asked questions

How much does a South Shore vacation package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a vacation to South Shore costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to South Shore?
To pick up cheap South Shore vacation packages, plan your getaway outside of busy periods like public holidays and major festivals. You'll generally find lower prices and better availability in the off-season or when it's less busy.
How many days is enough for South Shore?
Typically, a handful of days is enough to visit the main sights during your South Shore vacation. But if you prefer to have some time to rest or go on day tours, consider extending your trip.
How to find the best South Shore package deals?
Finding a cheap South Shore package deal is easy with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can tailor your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to view the most economical South Shore package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a South Shore vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking flights and stays separately. Better still, you can tailor your South Shore escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to South Shore?
If you've got your South Shore travel dates finalized, book as soon as you can to snap up some fantastic deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for travelling on a whim.
How to plan a trip to South Shore?
  1. Choose your dates: What you want to do in South Shore and your favourite season will help you decide when to go.
  2. Figure out your budget: Make sure you have enough money to cover everything from food and transportation to experiences and flights. Your accommodations will probably be the largest expense during your trip to South Shore.
  3. Work out your trip length: Consider how long you want to spend exploring South Shore. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to find a South Shore vacation package that brings all your bookings together.

Explore a world of travel with Expedia

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