Paintsville Vacations from $469

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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.
Oak Tree Inn

Oak Tree Inn

2 out of 5
Price was $790, price is now $469 per person
$469
per person
Jul 27 - Jul 31
found 12 hours ago
Roundtrip flight included
New York (JFK) to Lexington (LEX)
6/10 (21 reviews)
Window curtains too sheer, too many bird feces on railing/stairs

Reviewed on Mar 28, 2026

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

2.5 out of 5
Price was $829, price is now $487 per person
$487
per person
Jul 27 - Jul 31
found 12 hours ago
Roundtrip flight included
New York (JFK) to Lexington (LEX)
7.2/10 Good! (800 reviews)
The hotel provides value for the cost. Staff, facilities, and maintenance were above average for a budget hotel.

Reviewed on Apr 22, 2026

Ramada Limited Mount Sterling

Ramada Limited Mount Sterling

2 out of 5
Price was $853, price is now $505 per person
$505
per person
Jul 27 - Jul 31
found 12 hours ago
Roundtrip flight included
New York (JFK) to Lexington (LEX)
7/10 Good! (812 reviews)
The jetted tub in the room was absolutely perfect.

Reviewed on May 13, 2026

Comfort Inn & Suites Mount Sterling

Comfort Inn & Suites Mount Sterling

2.5 out of 5
Price was $907, price is now $555 per person
$555
per person
Jul 27 - Jul 31
found 1 day ago
Roundtrip flight included
New York (NYC) to Lexington (LEX)
7.8/10 Good! (745 reviews)
Very clean and comfortable stay!! The stay were very attentive, welcoming, and helpful!

Reviewed on May 10, 2026

Holiday Inn Express & Suites Mt Sterling North by IHG

Holiday Inn Express & Suites Mt Sterling North by IHG

2.5 out of 5
Price was $969, price is now $620 per person
$620
per person
Jul 27 - Jul 31
found 12 hours ago
Roundtrip flight included
New York (JFK) to Lexington (LEX)
8.8/10 Excellent! (607 reviews)
Great staff. The shower door leaked and the light blocking shade would only go up halfway making the room dark.

Reviewed on Apr 11, 2026

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See all available trips from Columbus to Paintsville
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Discover the most popular places to visit in Paintsville

Serene Walking Path to Rustic Wooden Bridge in Green Forest

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

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

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
$115 nightly
The price is $127 total per night from May 31 to Jun 1
$127 total
May 31 - Jun 1
Total with taxes and fees
8.8/10 Excellent! (578 reviews)
"Very nice property. Front desk staff were not at all friendly. Felt like we were bothering them."

Reviewed on May 19, 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
$71 nightly
The price is $78 total per night from May 25 to May 26
$78 total
May 25 - May 26
Total with taxes and fees
7.6/10 Good! (540 reviews)
"Th room was clean. Excellent breakfast except for the coffee. Parking was fine. The back on the desk chair was broken. There was no room service."

Reviewed on May 17, 2026

Days Inn by Wyndham Paintsville
Private 2BR Renovated Guest Suite in Historic Home with Kitchen

Private 2BR Renovated Guest Suite in Historic Home with Kitchen

Paintsville KY
Get rates
Private 2BR Renovated Guest Suite in Historic Home with Kitchen
See all 59 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 $469 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.