Paintsville Vacation Packages

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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.

Top Paintsville Vacation Deals

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

3 out of 5
per person
Aug 28 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Lexington (LEX)
8.6/10 Excellent! (1,221 reviews)
Nice renovation. Chocolate chip cookies in lobby.

Reviewed on Jul. 24, 2025

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
per person
Aug 28 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Lexington (LEX)
8.8/10 Excellent! (1,003 reviews)
Lovely hotel and beautiful art/cocktails/info provided However the air con was so cold even though set to 19.5 We couldn’t get it right And the cleaning wasn’t up to a scratch We loved the bar area and the bar man was so friendly An overall good stay

Reviewed on Jul. 24, 2025

The Campbell House Lexington, Curio Collection by Hilton

The Campbell House Lexington, Curio Collection by Hilton

4 out of 5
per person
Aug 28 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Lexington (LEX)
8/10 Very Good! (1,005 reviews)
Decent hotel but no free breakfast, no complementary coffee, and got charged $12 bucks to park. Room was clean and updated albeit the paint job was shoddy.

Reviewed on Jul. 19, 2025

Tru by Hilton University Medical Center

Tru by Hilton University Medical Center

2.5 out of 5
South Broadway Park
per person
Aug 28 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Lexington (LEX)
9.2/10 Wonderful! (369 reviews)
The room was clean and comfortable. The staff was very friendly and informative. Loved the stay!

Reviewed on Jul. 20, 2025

Staybridge Suites Lexington S Medical Ctr Area by IHG

Staybridge Suites Lexington S Medical Ctr Area by IHG

3 out of 5
per person
Aug 28 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Lexington (LEX)
9.8/10 Exceptional! (390 reviews)
I arrived an hour early. The front desk said i could not get an early check-in. She did allow us

Reviewed on Jul. 22, 2025

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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
The price is CA $150 per night from Aug 10 to Aug 11
CA $150
CA $166 total
Aug 10 - Aug 11
includes taxes & fees
8.6/10 Excellent! (511 reviews)
Great choice.
"Only one other option in the town. NO comparison to quality.The other one was old with outside entrances. This one had everything you need and it was convenient."

Reviewed on Jul. 24, 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
The price is CA $93 per night from Aug 10 to Aug 11
CA $93
CA $102 total
Aug 10 - Aug 11
includes taxes & fees
7.4/10 Good! (470 reviews)
"Quiet, clean, reasonable rates."

Reviewed on Jul. 15, 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 57 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 CA $970 on Expedia for your Paintsville escape. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Paintsville costs.
What are the cheapest months to go to Paintsville?
December, January and February are the best times to search for cheap Paintsville vacation packages. Choosing to travel in less busy periods means you'll typically find better prices on flights and hotels.
How many days is enough for Paintsville?
With a well-organized travel plan, you can easily hit the most popular Paintsville attractions in a handful of days. But if you'd like to discover hidden gems or go on day trips, think about booking your Paintsville vacation for longer.
Is it worth booking a vacation package to Paintsville?
Paintsville has everything you need for an amazing break — hiking, nature and walking trails are just the start. Whether you want to check out sights like Paintsville Country Club and Paintsville Golf Course, or venture off the beaten track, you'll find plenty to do on your Paintsville vacation.
How to find the best Paintsville package deals?
Landing a cheap Paintsville package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget range, apply some filters and see what's available. You can customize your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most economical Paintsville package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Paintsville vacation as a package?
You can enjoy significant savings on your next Paintsville retreat by booking a personalized vacation package. Check the "Package" heading, then enter your travel dates and destination to browse some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Paintsville?
Enjoy amazing discounts by booking your flights early with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for an impromptu Paintsville trip.
How to plan a trip to Paintsville?

  1. Pick the ideal time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to travel to Paintsville.
  2. Plan your budget wisely: On top of the cost of your stay, you should factor in other expenses. These include food, transportation and flights. Also, put aside some extra funds for unexpected expenses that may come up during your trip to Paintsville.
  3. Decide how many days away: Start by compiling a list of the activities and sights you'd like to experience in Paintsville. Then, estimate how long you'll need for each, along with any travel time.
  4. Combine your airfare and accommodations: After you've nailed down your travel dates and duration, book the right Paintsville vacation package for you.

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