Paintsville Vacation Packages
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Your Paintsville Vacation
Our vacation packages to Paintsville provide endless opportunities to discover new sights, sounds and sensations. And with all the travel planning taken care of, you'll be free to enjoy your city escape without a worry in the world. Every trip to Paintsville needs a well-designed itinerary. Fill yours with major attractions such as U.S. 23 Country Music Highway Museum, Loretta Lynns Birthplace - Butcher Hollow and Paintsville Lake State Park. Expedia will help you escape your daily routine. Tailor your vacation to Paintsville to suit your style of travel, whatever that may look like.
Top Paintsville Vacation Deals
Price found within the past 48 hours. Click for updated prices.
GuestHouse Lexington
CA $1,323
per person
Oct 6 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Lexington (LEX)
8.4/10 Very good! (1,641 reviews)
Highly recommend for traveling families. Room was quiet and clean and well maintained. Staff was helpful. Breakfast was minimal and simple, but was good.
Reviewed on Aug 22, 2026
Elwood Hotel & Suites
CA $2,595
per person
Oct 6 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Lexington (LEX)
9.4/10 Exceptional! (1,132 reviews)
Great place to stay for moving our daughter in to UK. Convenient location, comfortable and clean room and hotel, friendly and helpful staff.
Reviewed on Aug 18, 2026
Ready to book your vacation to Paintsville?
Paintsville Hotel Deals
Days Inn by Wyndham Paintsville
512 S Mayo Trail Paintsville KY
Fully refundableReserve now, pay when you stay
CA $99
CA $110 total
Aug 25 - Aug 26
includes taxes & fees
Ramada Hotel & Conference Center by Wyndham Paintsville
624 James Trimble Blvd Paintsville KY
Fully refundableReserve now, pay when you stay
CA $163
CA $179 total
Aug 30 - Aug 31
includes taxes & fees
Budget Inn Express
709 S Mayo Trail Paintsville KY
CA $108
CA $120 total
Aug 24 - Aug 25
includes taxes & fees
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)
You can learn about the history of Paintsville with a visit to Walking Bridge. Discover the area's mountain views and countryside.
U. S. 23 Country Music Highway Museum
6.0/10 (8 reviews)
You can spend an afternoon studying the exhibits at U. S. 23 Country Music Highway Museum during your travels in Paintsville. Discover the area's mountain views and countryside.
Preston Park
Explore the great outdoors at Preston Park, a lovely green space in Paintsville. Stroll along the marina or discover the mountain views in this family-friendly area.
Paintsville Golf Course
5.6/10 (9 reviews)
Enjoy a round of golf in Paintsville at Paintsville Golf Course. Discover the area's mountain views and countryside.
Mayo Mansion
You can find out about the history of Paintsville with a stop at Mayo Mansion. Discover the mountain views and monuments in this family-friendly area.
Paintsville ARH Hospital
Though Paintsville ARH Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Paintsville while you are here.
Swamp Branch Trailhead
You can take time to visit Swamp Branch Trailhead during your travels to Paintsville. Discover the mountain views and monuments in this family-friendly area.
Johnson County Public Library
After visiting Johnson County Public Library, make a plan to see the other sights and activities in Paintsville. Wander the marina or discover the mountain views in this family-friendly area.
Frequently asked questions
How much does a Paintsville vacation package cost?
You'll find cheap prices from CA $1,323 on Expedia for your Paintsville escape. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Paintsville costs.
What are the cheapest months to go to Paintsville?
December, January and February are the best times to search for cheap Paintsville vacation packages. Choosing to travel in less busy periods means you'll typically find better prices on flights and hotels.
How many days is enough for Paintsville?
With a well-organized travel plan, you can easily hit the most popular Paintsville attractions in a handful of days. But if you'd like to discover hidden gems or go on day trips, think about booking your Paintsville vacation for longer.
Is it worth booking a vacation package to Paintsville?
Paintsville has everything you need for an amazing break — hiking, nature and walking trails are just the start. Whether you want to check out sights like Paintsville Country Club and Paintsville Golf Course, or venture off the beaten track, you'll find plenty to do on your Paintsville vacation.
How to find the best Paintsville package deals?
Landing a cheap Paintsville package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget range, apply some filters and see what's available. You can customize your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most economical Paintsville package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Paintsville vacation as a package?
You can enjoy significant savings on your next Paintsville retreat by booking a personalized vacation package. Check the "Package" heading, then enter your travel dates and destination to browse some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Paintsville?
Enjoy amazing discounts by booking your flights early with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for an impromptu Paintsville trip.
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 influence your decision on when to travel to Paintsville.
- Plan your budget wisely: On top of the cost of your stay, you should factor in other expenses. These include food, transportation and flights. Also, put aside some extra funds for unexpected expenses that may come up during your trip to Paintsville.
- Decide how many days away: Start by compiling a list of the activities and sights you'd like to experience in Paintsville. Then, estimate how long you'll need for each, along with any travel time.
- Combine your airfare and accommodations: After you've nailed down your travel dates and duration, book the right Paintsville vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
