Paintsville Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Paintsville
Days Inn by Wyndham Paintsville
512 S Mayo Trail Paintsville KY
Fully refundableReserve now, pay when you stay
S$102
11 Aug - 12 Aug
includes taxes & fees
Ramada Hotel & Conference Center by Wyndham Paintsville
624 James Trimble Blvd Paintsville KY
Fully refundableReserve now, pay when you stay
S$166
16 Aug - 17 Aug
includes taxes & fees
8.8/10 Excellent! (607 reviews)
"Very nice hotel with clean rooms and friendly staff members."
Reviewed on 5 Aug, 2026
Downtown Paintsville Vacation Rental!
217 3rd St Paintsville KY
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.
Stay near popular Paintsville attractions
Walking Bridge
10.0/10 (4 reviews)
The world's longest plastic-deck pedestrian bridge spans 420 feet across River, Kentucky. Stroll this engineering marvel for serene views and a peaceful escape from the everyday bustle.
U. S. 23 Country Music Highway Museum
6.0/10 (8 reviews)
This Eastern Kentucky shrine celebrates country music legends like Loretta Lynn and The Judds with personal memorabilia. Catch weekly "Front Porch Pickin'" sessions for authentic local bluegrass.
Preston Park
Preston Park offers a serene retreat with its central gazebo, fountain, and vibrant seasonal flower beds in Paintsville. Enjoy a peaceful afternoon stroll while admiring the meticulously maintained gardens.
Mayo Mansion
The Mayo Mansion stands as a testament to Kentucky's coal heritage with its grand Classical Revival architecture. Tour this 43-room historical residence by appointment to glimpse early 20th-century opulence.
Paintsville ARH Hospital
If Paintsville ARH Hospital is what brings you to town, hopefully you'll have a chance to explore more of Paintsville.
Swamp Branch Trailhead
Gateway to the scenic Dawkins Line Rail Trail, this trailhead connects visitors to eastern Kentucky's natural splendour. Hikers and cyclists traverse picturesque bridges and paths once used by the historic railway.
Paintsville Golf Course
5.6/10 (9 reviews)
Historic Paintsville Golf Course challenges players with rolling fairways and dramatic river crossings. Experience one of Eastern Kentucky's first 18-hole courses, featuring a swinging bridge over the Big Sandy River.
Johnson County Public Library
This community hub houses rich local history collections and offers diverse educational programmes for all ages. Explore the genealogy section or join a gentle yoga session in this welcoming space for lifelong learning.
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?
- 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.
- 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.
- 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.
- 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.
