Paintsville Vacations from $395

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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.
DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

4 out of 5
per person
Aug 23 - Aug 26
found 24 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Lexington (LEX)
8.6/10 Excellent! (1,008 reviews)
Top tier hotel to stay in. 10/10 would recommend, and I most definitely will be staying again.

Reviewed on Jul 6, 2025

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
per person
Aug 23 - Aug 26
found 24 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Lexington (LEX)
8.8/10 Excellent! (1,000 reviews)
Lovely spacious room. Fabulous art throughout!

Reviewed on Jul 6, 2025

The Manchester

The Manchester

4 out of 5
Distillery District
per person
Aug 23 - Aug 26
found 24 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Lexington (LEX)
9.6/10 Exceptional! (906 reviews)
Fantastic property! The best hotel I’ve stayed at this year. The room was clean. The decor was fantastic. Bed was comfy. Loved the rooftop bar. And the restaurant is in the distillery district so super close to great restaurants, shops and bourbon. We will go back!

Reviewed on Jul 10, 2025

The Sire Hotel Lexington, Tapestry Collection by Hilton

The Sire Hotel Lexington, Tapestry Collection by Hilton

3.5 out of 5
Downtown Lexington
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Lexington (LEX)
9.4/10 Exceptional! (809 reviews)
Very nice staff. Room was great. Very clean. Comfortable bed. Definitely would stay here again

Reviewed on Jul 12, 2025

Hyatt Regency Lexington

Hyatt Regency Lexington

3.5 out of 5
Downtown Lexington
per person
Aug 23 - Aug 26
found 24 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Lexington (LEX)
8.6/10 Excellent! (1,006 reviews)
This property is old and in serious need of updating. The Expedia pictures do not match the property itself. This property was way overpriced for its condition. There was so much dust behind the mirror in the bathroom I actually saw a dust bunny fall.

Reviewed on Jul 11, 2025

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Discover the most popular places to visit in Paintsville

U. S. 23 Country Music Highway Museum

4/5(1 review)

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

3.5/5(3 reviews)

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

Paintsville Golf Course

Walking Bridge

5/5(4 reviews)

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

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
$111 nightly
The price is $122 total per night from Jul 20 to Jul 21
$122 total
Jul 20 - Jul 21
Total includes taxes and fees
8.6/10 Excellent! (501 reviews)
"Close drive to shopping and a short walk to downtown across the street is the hospital. Pool was great little crowded but is was 4th of July weekend."

Reviewed on Jul 9, 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
$68 nightly
The price is $75 total per night from Jul 20 to Jul 21
$75 total
Jul 20 - Jul 21
Total includes taxes and fees
7.4/10 Good! (464 reviews)
"It was a Nice Hotel to sleep in for just passing thur"

Reviewed on Jun 19, 2025

Days Inn 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 56 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.

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 $395 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.