South Shore Vacations from $700

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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.
Super 8 by Wyndham Grayson
DoubleTree by Hilton Huntington
Knights Inn Ashland
Rodeway Inn
Holiday Inn Express & Suites Ironton by IHG
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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
$89 nightly
The price is $98 total per night from Nov 4 to Nov 5
$98 total
Nov 4 - Nov 5
Total with taxes and fees
9/10 Wonderful! (465 reviews)
"Very convenient to the Highway. Property lacked sufficient parking and the grounds had minimal landscaping, etc, but the room was very clean and comfortable. I thought the rate was a bit high for the property, but I would stay here again."

Reviewed on Oct 30, 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
$132 nightly
The price is $154 total per night from Nov 15 to Nov 16
$154 total
Nov 15 - Nov 16
Total with taxes and 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
Fully refundableReserve now, pay when you stay
$64 nightly
The price is $71 total per night from Nov 5 to Nov 6
$71 total
Nov 5 - Nov 6
Total with taxes and fees
9/10 Wonderful! (375 reviews)
"Not pet friendly and needs new management."

Reviewed on Nov 1, 2026

Greenbo Lake 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.

Find the Best South Shore Vacation Packages

South Shore Essential Information

Language
English
Currency
U.S dollars
Population
1,100
Max Temp Winter
40ºF
Max Temp Summer
85ºF

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Frequently asked questions

What's included in a South Shore vacation package?
A South Shore vacation package lets you combine round-trip flights, hotel stays, and rental cars. Many hotels in South Shore offer free breakfast, providing a convenient start to your day. Most properties also include free parking, making it easy to explore the surrounding natural attractions.

Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
How can I save money on a South Shore vacation package?
When you bundle, you can save up to 30%*. To save money on a South Shore package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What are the top things to do in South Shore?
A South Shore vacation offers a variety of outdoor activities and family-friendly attractions, making it an ideal outdoor and nature destination. Consider these top sights for your trip:

Browse and book things to do in South Shore on Expedia.
Do you need to rent a car in South Shore, or is public transport enough?
For a South Shore vacation package, a rental car is highly recommended to fully explore this outdoor and nature destination. Attractions like Greenbo Lake State Resort Park (about 10 miles away) and Carter Caves State Park (about 19 miles away) are spread out, making a car essential for convenient access. While some areas like the Boneyfiddle Commercial District (about 4 miles from central South Shore) might be walkable, a car offers the flexibility to visit various state parks and other sights at your own pace. South Shore vacation packages with flights typically do not include ground transportation, so arranging a rental car is a practical choice for your trip.
Can I change or cancel my South Shore vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking South Shore vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later South Shore vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your South Shore vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to South Shore?
To find last-minute vacation packages to South Shore, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on South Shore vacation packages?
Free cancellation on a South Shore vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a South Shore vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your South Shore getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my South Shore vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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