Paintsville Vacations from $613
Book a Hotel + Flight or Car together to unlock savings
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.
The Latest Paintsville vacation packages
Price found within the past 48 hours. Click for updated prices.
1851 Historic Maple Hill Manor B&B
$665
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Lexington (LEX)
9.4/10 Exceptional! (645 reviews)
Maple Hill Manor is a very large (really! the ceilings are 14’ high throughout), beautiful B&B located in Kentucky’s bourbon country. The rooms are gorgeous, and the home—once used as a Civil War field hospital following the Battle of Perryville—has a long and storied history. Maple Hill stands out among other similarly historic B&Bs not just for its grand physical scale, but also for the friendliness of the owners and the fantastic food. Among all the historic B&Bs I’ve stayed at, Maple Hill has the best breakfast. They also serve homemade dessert in the evening, which is a fantastic touch. Animal lovers will appreciate that there are some friendly horses and donkeys on the grounds that enjoy attention from visitors. Maple Hill is about a 20-minute drive from dining options in nearby historic Bardstown.
Reviewed on Aug 28, 2026
Wildflower Ranch Inn
$640
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Lexington (LEX)
9.2/10 Wonderful! (24 reviews)
Carol and Rich were wonderful hosts!
They made sure we had everything we needed, were very accommodating, and served 5 star breakfasts. The pool was sublime, the sun room was magical. We can’t say enough about how special we felt during our stay!
Reviewed on Aug 17, 2026
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View all tripsStay 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 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.
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
Gateway to the scenic Dawkins Line Rail Trail, this trailhead connects visitors to eastern Kentucky's natural splendor. Hikers and cyclists traverse picturesque bridges and paths once used by the historic railroad.
Johnson County Public Library
This community hub houses rich local history collections and offers diverse educational programs for all ages. Explore the genealogy section or join a gentle yoga session in this welcoming space for lifelong learning.
Paintsville Hotel Deals
Days Inn by Wyndham Paintsville
512 S Mayo Trail Paintsville KY
Fully refundableReserve now, pay when you stay
$71 nightly
$79 total
Sep 12 - Sep 13
Total with taxes and fees
Ramada Hotel & Conference Center by Wyndham Paintsville
624 James Trimble Blvd Paintsville KY
Fully refundableReserve now, pay when you stay
$118 nightly
$130 total
Sep 13 - Sep 14
Total with taxes and fees
Budget Inn Express
709 S Mayo Trail Paintsville KY
Fully refundableReserve now, pay when you stay
$78 nightly
$86 total
Sep 10 - Sep 11
Total with taxes and 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.
Find the Best Paintsville Vacation Packages
Paintsville Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 4,200 |
Max Temp Winter | 45ºF |
Max Temp Summer | 85ºF |
Top Sights | Paintsville Lake State Park, Mountain HomePlace and Loretta Lynns Birthplace - Butcher Hollow |
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Frequently asked questions
How much does a Paintsville vacation package cost?
You'll find cheap prices from $613 on Expedia for your Paintsville getaway. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Paintsville costs.
What are the cheapest months to go to Paintsville?
November, December and January are the best times to look for cheap Paintsville vacation packages. Choosing to travel in less busy months means you'll typically find better prices on flights and accommodations.
How many days is enough for Paintsville?
With a well-organized travel plan, you can easily hit the top Paintsville attractions in a few days. But if you want to explore off the beaten track or take day trips, think about booking your Paintsville vacation for longer.
Is it worth booking a vacation package to Paintsville?
Whether you're looking to explore top sights such as Paintsville Country Club and Paintsville Golf Course on your Paintsville vacation, or coming for its excellent hiking, nature and walking trails, there's something for everyone here. With so many things to see and do, you'll quickly learn why so many families think Paintsville is a good vacation destination.
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 vacation as a package?
Expedia vacation 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 customized Paintsville vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation 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.
Does Expedia offer Book Now, Pay Later Paintsville vacation packages?
Jet off on your dream trip to Paintsville with our Book Now, Pay Later vacations. There's no need to scrimp and save or wait for your next paycheck — we've partnered with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to budget for your trip and snap up cheap deals while they last.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.