Paintsville Vacations

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  • Better together

    Save up to AEDĀ 5,000 when you book a flight and hotel together*

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Find the Best Paintsville Vacation Packages

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
The price is AEDĀ 434 per night from Aug 16 to Aug 17
AEDĀ 434
AEDĀ 478 total
16 Aug - 17 Aug
includes taxes & fees
8.8/10 Excellent! (594 reviews)
"This is a hidden gem in the mountains of EKY!"

Reviewed on 15 July 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
The price is AEDĀ 281 per night from Jul 21 to Jul 22
AEDĀ 281
AEDĀ 310 total
21 Jul - 22 Jul
includes taxes & fees
7.6/10 Good! (560 reviews)
"Stayed here several times,always a good experience."

Reviewed on 16 July 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
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Private 2BR Renovated Guest Suite in Historic Home with Kitchen
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.

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.
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Frequently asked questions

How much does a Paintsville vacation package cost?
You'll find cheap prices 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 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," "Traveler 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 traveling 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, favorite 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.