Olive Hill Holidays

Photo by Cat Sobral

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Top hotels in Olive Hill

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$227 per night from 6 Sept to 7 Sept
S$227
6 Sept - 7 Sept
includes taxes & fees
9/10 Wonderful! (634 reviews)
"This is an older property with all the charm you would expect. They have done a great job of upkeep, providing clean and comfortable rooms while still mixing in the feel of a cabin. Relaxing, safe, and beautiful. Will stay again!"

Reviewed on 24 Aug, 2025

Carter Caves State Resort Park
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$126 per night from 1 Sept to 2 Sept
S$126
1 Sept - 2 Sept
includes taxes & fees
Fairfield Inn & Suites By Marriott Ashland
Holiday Inn Express & Suites Ashland by IHG

Holiday Inn Express & Suites Ashland by IHG

2.5 out of 5
13131 Slone Court, Ashland, KY
Fully refundable
The price is S$171 per night from 5 Sept to 6 Sept
S$171
5 Sept - 6 Sept
includes taxes & fees
Holiday Inn Express & Suites Ashland by IHG
See all 136 properties in Olive Hill
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 an Olive Hill holiday package cost?
You can pick up a holiday package to this top destination on Expedia. But how much your holiday to Olive Hill costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Olive Hill?
December, January and February are great times to look for cheap Olive Hill holiday packages. Opting to travel in quieter months means you can typically find reduced prices on flights and hotels.
How many days is enough for Olive Hill?
Typically, a handful of days is enough to see the main attractions during your Olive Hill holiday. However, if you'd like to have time to unwind or go on day trips, think about extending your itinerary.
How to find the best Olive Hill package deals?
Use Expedia's filters to find some great Olive Hill package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Olive Hill package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your holiday package as soon as possible.
Is it cheaper to book an Olive Hill holiday as a package?
An Expedia holiday package could land you significant savings when compared to booking flights and stays separately. Better still, you can tailor your Olive Hill trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a holiday package to Olive Hill?
If you're planning a spur-of-the-moment Olive Hill trip, browse 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 hotels and flights by booking ahead.
How to plan a trip to Olive Hill?

  1. Choose when to go: Check your diary and get packing. Your preferred season and the activities on offer will also help you decide when to escape to Olive Hill.
  2. Plan your budget wisely: On top of the cost of your accommodation, you'll need to consider other expenses too. These include food, flights and transportation. Also, put aside a little extra for unexpected costs that could crop up during your trip to Olive Hill.
  3. Decide how long to go away for: Now that you're more familiar with Olive Hill, you can figure out the perfect length of your break. Create a rough itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your accommodation and airfare: After you've nailed down your trip dates and duration, lock in the perfect Olive Hill 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.