Paintsville Vacations from $723

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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.
Clarion Hotel Conference Center Lexington North

Clarion Hotel Conference Center Lexington North

3 out of 5
Price was $909, price is now $723 per person
$723
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
New York (NYC) to Lexington (LEX)
7.6/10 Good! (1,007 reviews)
Room was clean as well as lobby and breakfast area. Remodeling was going on and no ceiling in first floor showing all electrical wires. Outside road construction was going on all night making it difficult to sleep. Staff was nice and helpful went to make sure room door was shut because it would stick and couldn’t remember if shut it completely.

Reviewed on Oct 30, 2026

Fairfield Inn & Suites Lexington Keeneland Airport

Fairfield Inn & Suites Lexington Keeneland Airport

3 out of 5
Beaumont Residential
Price was $993, price is now $787 per person
$787
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
New York (NYC) to Lexington (LEX)
8.8/10 Excellent! (792 reviews)

Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

3 out of 5
Price was $940, price is now $758 per person
$758
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
New York (NYC) to Lexington (LEX)
8.6/10 Excellent! (1,022 reviews)

Bluegrass Inn

Bluegrass Inn

2 out of 5
Price was $935, price is now $760 per person
$760
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
New York (NYC) to Lexington (LEX)
8/10 Very Good! (1,006 reviews)
Room was clean, quiet, and well kept

Reviewed on Oct 30, 2026

Courtyard Lexington Keeneland/Airport

Courtyard Lexington Keeneland/Airport

3 out of 5
Beaumont Residential
Price was $984, price is now $810 per person
$810
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
New York (NYC) to Lexington (LEX)
8.8/10 Excellent! (867 reviews)
Great staff clean rooms lovely bartender

Reviewed on Sep 28, 2026

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Stay 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.
See properties

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
$110 nightly
The price is $121 total per night from Nov 8 to Nov 9
$121 total
Nov 8 - Nov 9
Total with taxes and fees
8.8/10 Excellent! (631 reviews)
"Took forever to get checked in. The young boy behind the counter couldn’t find my reservation. Then after 15 minutes he found it, then said I was already checked in and was in my room. So after another 10 minutes I was checked in and had my key card. Once in the room it was just your ordinary (2 ..."

Reviewed on Oct 31, 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
$72 nightly
The price is $80 total per night from Nov 3 to Nov 4
$80 total
Nov 3 - Nov 4
Total with taxes and fees
Days Inn by Wyndham Paintsville
Budget Inn Express

Budget Inn Express

709 S Mayo Trail Paintsville KY
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $81 total per night from Nov 30 to Dec 1
$81 total
Nov 30 - Dec 1
Total with taxes and fees
8/10 Very Good! (1 review)
"The budget inn was a reasonable place for the price. I would stay there again."

Reviewed on Oct 28, 2026

Budget Inn Express
See all 70 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 $723 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.