Paintsville Vacations from $384

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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.
Comfort Inn & Suites Lexington - Hamburg I-75

Comfort Inn & Suites Lexington - Hamburg I-75

2.5 out of 5
Price was $449, price is now $384 per person
$384
per person
Feb 19 - Feb 22
found 12 hours ago
Roundtrip non-stop flight included
New York (NYC) to Lexington (LEX)
8/10 Very Good! (1,004 reviews)
Need more time for breakfast and better choices. Marriott have better and more options. With a group of high school athletes need to eat before playing sports.

Reviewed on Dec 29, 2025

The Sire Hotel Lexington, Tapestry Collection by Hilton

The Sire Hotel Lexington, Tapestry Collection by Hilton

3.5 out of 5
Downtown Lexington
Price was $724, price is now $574 per person
$574
per person
Feb 19 - Feb 22
found 12 hours ago
Roundtrip non-stop flight included
New York (NYC) to Lexington (LEX)
9.4/10 Exceptional! (838 reviews)
Absolutely wonderful! You have to stay in this historic building. Gorgeous rooms.

Reviewed on Dec 15, 2025

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was $609, price is now $493 per person
$493
per person
Feb 19 - Feb 22
found 10 hours ago
Roundtrip non-stop flight included
New York (NYC) to Lexington (LEX)
8.8/10 Excellent! (1,002 reviews)
The room was nice and the views were great

Reviewed on Jan 4, 2026

The Campbell House Lexington, Curio Collection by Hilton

The Campbell House Lexington, Curio Collection by Hilton

4 out of 5
Price was $580, price is now $483 per person
$483
per person
Feb 19 - Feb 22
found 10 hours ago
Roundtrip non-stop flight included
New York (NYC) to Lexington (LEX)
8.2/10 Very Good! (1,000 reviews)
Only spent the night

Reviewed on Dec 31, 2025

Capital Plaza Hotel

Capital Plaza Hotel

3 out of 5
Price was $742, price is now $639 per person
$639
per person
Feb 13 - Feb 17
found 11 hours ago
Roundtrip non-stop flight included
New York (JFK) to Lexington (LEX)
8.2/10 Very Good! (1,040 reviews)
Awesome! We noticed a flyer for a bourbon tasting on the counter during check in featuring four Rip Van Winkle pours. We rearranged our dinner plans and had a fabulous evening!

Reviewed on Dec 27, 2025

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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

Ramada Hotel & Conference Center by Wyndham Paintsville

Ramada Hotel & Conference Center by Wyndham Paintsville

2.5 out of 5
624 James Trimble Blvd Paintsville KY
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $119 total per night from Jan 13 to Jan 14
$119 total
Jan 13 - Jan 14
Total with taxes and fees
8.6/10 Excellent! (551 reviews)
Everything was great. The only exception being that we could never swim in the pool. Every time we wanted to use it, there were unattended children there. We should have probably reported it at that time. Otherwise the place of was great.

Reviewed on Jan 2, 2026

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 Jan 9 to Jan 10
$75 total
Jan 9 - Jan 10
Total with taxes and fees
7.6/10 Good! (514 reviews)
Had the greatest and most compassionate staff.

Reviewed on Dec 8, 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 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.

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 $384 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.