Paintsville Vacations from $428

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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.

The Latest Paintsville vacation packages

Price found within the past 48 hours. Click for updated prices.
Motel 6 Lexington, KY - East I-75

Motel 6 Lexington, KY - East I-75

2 out of 5
Price was $564, price is now $428 per person
$428
per person
Oct 4 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Lexington (LEX)
7/10 Good! (1,000 reviews)
I have always enjoyed staying at the Motel 6.

Reviewed on Aug 18, 2025

Hotel LEX, Trademark Collection by Wyndham

Hotel LEX, Trademark Collection by Wyndham

3 out of 5
Price was $774, price is now $597 per person
$597
per person
Oct 4 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Lexington (LEX)
8.4/10 Very Good! (473 reviews)
The property was nice, pretty clean. Bed was comfortable. Only con was a lot of ants in bathroom.

Reviewed on Aug 18, 2025

Microtel Inn by Wyndham Lexington

Microtel Inn by Wyndham Lexington

2.5 out of 5
Price was $781, price is now $621 per person
$621
per person
Oct 4 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Lexington (LEX)
6.8/10 (1,002 reviews)
Love it always a stay

Reviewed on Aug 13, 2025

Home2 Suites by Hilton Lexington University / Medical Center

Home2 Suites by Hilton Lexington University / Medical Center

3 out of 5
Zandale
Price was $796, price is now $640 per person
$640
per person
Oct 4 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Lexington (LEX)
8.8/10 Excellent! (982 reviews)
Closeness to shopping and eateries

Reviewed on Aug 19, 2025

Comfort Inn Lexington I-75

Comfort Inn Lexington I-75

2.5 out of 5
Price was $684, price is now $560 per person
$560
per person
Oct 4 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Lexington (LEX)
7.4/10 Good! (680 reviews)
Breakfast is ok ,parking is nice . The rooms are smelly.

Reviewed on Aug 13, 2025

Don't see what you're looking for?
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Discover the most popular places to visit in Paintsville

U. S. 23 Country Music Highway Museum

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.

U. S. 23 Country Music Highway Museum

Paintsville Golf Course

Enjoy a round of golf in Paintsville at Paintsville Golf Course. Discover the area's mountain views and countryside.

Paintsville Golf Course

Walking Bridge

You can learn about the history of Paintsville with a visit to Walking Bridge. Discover the area's mountain views and countryside.

Walking Bridge

Paintsville Hotel Deals

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
$64 nightly
The price is $70 total per night from Sep 7 to Sep 8
$70 total
Sep 7 - Sep 8
Total with taxes and fees
7.4/10 Good! (477 reviews)
Good hotel, wrong city
"Hotel was good. Location was not. Not the Hotels fault. When booking online in the Hotels app, I put in Pikesville KY and searched. Second choice was this hotel. But it was in Paintsville KY 40 miles away in the wrong direction. I rechecked the app and it did this consistently offering hotels that ..."

Reviewed on Aug 19, 2025

Days Inn by Wyndham 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
$134 nightly
The price is $148 total per night from Aug 23 to Aug 24
$148 total
Aug 23 - Aug 24
Total with taxes and fees
8.6/10 Excellent! (521 reviews)
"Good location, ease of check in, welcoming staff. Traveling by motorcycle, they made special accommodations for safe parking."

Reviewed on Aug 19, 2025

Ramada Hotel & Conference Center by Wyndham Paintsville
Downtown Paintsville Vacation Rental!

Downtown Paintsville Vacation Rental!

3 out of 5
217 3rd St, Paintsville, KY
Get rates
Downtown Paintsville Vacation Rental!
See all 58 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.

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Frequently asked questions

How much does a Paintsville vacation package cost?
You'll find cheap prices from $428 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.