South Shore Holidays

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    Save up to S$134 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

Top hotels in South Shore

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
The price is S$131 per night from 1 Sept to 2 Sept
S$131
1 Sept - 2 Sept
includes taxes & 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 19 Aug, 2025

Fairfield Inn & Suites By Marriott Ashland
Knights Inn Ashland

Knights Inn Ashland

1.5 out of 5
7216 Sr 60, Ashland, KY
Fully refundableReserve now, pay when you stay
The price is S$92 per night from 7 Sept to 8 Sept
S$92
7 Sept - 8 Sept
includes taxes & 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 9 Aug, 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
The price is S$226 per night from 6 Sept to 7 Sept
S$226
6 Sept - 7 Sept
includes taxes & fees
9/10 Wonderful! (633 reviews)
New Family Getaway Spot
"Amazing and private resort that is kid friendly!"

Reviewed on 19 Aug, 2025

Carter Caves State Resort Park
See all 140 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 holiday package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a holiday to South Shore costs! Our packages simplify travel planning and maximise 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 holiday 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 holiday 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 holiday as a package?
Expedia holiday 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 customised South Shore holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday 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 favourite 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 accommodation: After you've nailed down your trip dates and duration, lock in the right South Shore holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.