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.
Capital Plaza Hotel

Capital Plaza Hotel

3 out of 5
Price was CA $882, price is now CA $818 per person
CA $818
per person
Sep 10 - Sep 12
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to Lexington (LEX)
8.2/10 Very good! (1,059 reviews)
Parking was safe an easy. Everything was great, but the hotel is under renovation and can’t give 5 stars due to that fac.

Reviewed on Jul 4, 2026

The Delegate

The Delegate

3.5 out of 5
Price was CA $993, price is now CA $966 per person
CA $966
per person
Sep 10 - Sep 12
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to Lexington (LEX)
9.2/10 Wonderful! (462 reviews)
Had a room above the restaurant and was very loud. Could hear ever

Reviewed on Jun 29, 2026

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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 Paintsville KY
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from Jul 26 to Jul 27
CA $163
CA $180 total
Jul 26 - Jul 27
includes taxes & fees
8.8/10 Excellent! (590 reviews)
"Nice clean hotel. Centrally located to many places."

Reviewed on Jun 20, 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 CA $103 per night from Jul 12 to Jul 13
CA $103
CA $113 total
Jul 12 - Jul 13
includes taxes & fees
7.6/10 Good! (557 reviews)
"Clean as always and very effortless check in as always.50plus year customer."

Reviewed on Jul 4, 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 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Paintsville attractions

Walking Bridge

10.0/10 (4 reviews)
You can learn about the history of Paintsville with a visit to Walking Bridge. Discover the area's mountain views and countryside.
See properties

Frequently asked questions

How much does a Paintsville vacation package cost?
You'll find cheap prices from CA $818 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.

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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.