Paintsville Holidays

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Paintsville

Ramada Hotel & Conference Center by Wyndham Paintsville
Ramada Hotel & Conference Center by Wyndham Paintsville
2.5 out of 5
624 James Trimble Blvd, Hwy 321 & James Trimble Blvd, Paintsville, KY
Fully refundableReserve now, pay when you stay
The price is S$157 per night from 13 Jul to 14 Jul
S$157
13 Jul - 14 Jul
includes taxes & fees
8.6/10 Excellent! (494 reviews)
"Nice room. Comfortable bed"

Reviewed on 11 Jun, 2025

Ramada Hotel & Conference Center by Wyndham Paintsville
Days Inn by Wyndham Paintsville
Days Inn by Wyndham Paintsville
2 out of 5
512 S Mayo Trail, Paintsville, KY
Fully refundableReserve now, pay when you stay
The price is S$96 per night from 24 Jun to 25 Jun
S$96
24 Jun - 25 Jun
includes taxes & fees
7.4/10 Good! (463 reviews)
"It was a Nice Hotel to sleep in for just passing thur"

Reviewed on 19 Jun, 2025

Days Inn by Wyndham Paintsville
Downtown Paintsville Vacation Rental!
Downtown Paintsville Vacation Rental!
3 out of 5
Paintsville
Get rates
Downtown Paintsville Vacation Rental!
See all 57 properties in Paintsville
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 Paintsville holiday package cost?
You'll find cheap prices on Expedia for your Paintsville getaway. However, factors like your choice of hotel, the season and length of stay will influence how much your holiday to Paintsville costs.
What are the cheapest months to go to Paintsville?
You can usually find lower rates and greater availability in December, January and February. Explore our cheap Paintsville holiday packages and you could land some excellent off-season deals.
How many days is enough for Paintsville?
With a well-planned itinerary, you can easily tick off the top Paintsville sights in a handful of days. But if you want to discover lesser-known spots or take day trips, think about booking your Paintsville holiday for longer.
Is it worth booking a holiday package to Paintsville?
Well known for its hiking, nature and walking trails, a Paintsville holiday offers something for everyone. Be sure to visit major sights like Paintsville Country Club and Paintsville Golf Course, and consider renting a car for day trips to experience even more.
How to find the best Paintsville package deals?
Begin your search for a Paintsville package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Paintsville package deal straight away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Paintsville getaway off to a flying start.
Is it cheaper to book a Paintsville holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll usually land a better deal than booking each component individually. And you'll still enjoy the freedom to create a customised Paintsville holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Paintsville?
Enjoy incredible discounts by booking your flights in advance with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for an impromptu Paintsville break.
How to plan a trip to Paintsville?

  1. Pick the ideal time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to travel to Paintsville.
  2. Budget wisely: In addition to the price of your accommodation, you should factor in other expenses. These include transportation, food and flights. Also, put aside a little extra for unexpected expenses that may crop up during your trip to Paintsville.
  3. Decide how long to go away for: Now that you're up to speed on Paintsville, you can figure out the ideal length of your holiday. Create a rough plan and allocate enough time to get through everything on your must-do list.
  4. Bundle your airfare and accommodation: Once you've settled on your dates and duration, book the right Paintsville 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.