Deals on vacations and trips to Paintsville

Save when you book Paintsville package deals

Choose two or more items and save on your trip:

Paintsville flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Capital Plaza Hotel

Capital Plaza Hotel

3 out of 5
Price was $524, price is now $469 per person
$469
per person
Feb 5 - Feb 8
found 3 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Lexington (LEX)
This hotel features a restaurant, an indoor pool, and a bar/lounge. There's a gym on site, and laundry facilities and concierge services are also offered.
21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was $603, price is now $498 per person
$498
per person
Feb 5 - Feb 8
found 3 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Lexington (LEX)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a 24-hour business center, and a snack bar/deli are also offered.
Montgomery Inn BnB

Montgomery Inn BnB

4 out of 5
Price was $665, price is now $588 per person
$588
per person
Feb 5 - Feb 8
found 3 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Lexington (LEX)
This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free full breakfast each morning. A terrace, a garden, and a lobby fireplace are also on offer.
Origin Lexington a Wyndham Hotel

Origin Lexington a Wyndham Hotel

3.5 out of 5
Price was $623, price is now $558 per person
$558
per person
Feb 5 - Feb 8
found 3 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Lexington (LEX)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 2 conference rooms, along with free WiFi in public areas. Free self parking and a coffee shop are also offered on site.
Embassy Suites by Hilton Lexington Green

Embassy Suites by Hilton Lexington Green

3.5 out of 5
Price was $570, price is now $516 per person
$516
per person
Feb 5 - Feb 8
found 3 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Lexington (LEX)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the seasonal outdoor pool and free perks like cooked-to-order breakfast and free self parking.

Top Paintsville hotels 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
Free Cancellation
Reserve now, pay when you stay
$108 nightly
The price is $119 total per night
$119 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
This hotel features an outdoor pool, an indoor pool, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
Pool
Hot Tub
Days Inn by Wyndham Paintsville

Days Inn by Wyndham Paintsville

2 out of 5
512 S Mayo Trail Paintsville KY
Free Cancellation
Reserve now, pay when you stay
$68 nightly
The price is $75 total per night
$75 total
Dec 30 - Dec 31
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Enjoy the outdoor pool and conveniences like a 24-hour front desk and laundry facilities.
Pool
Breakfast included
Downtown Paintsville Vacation Rental!

Downtown Paintsville Vacation Rental!

3 out of 5
217 3rd St Paintsville KY
Get rates
Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.
Kitchen
Parking included
Lovely 2 Bedroom Unit with Free Parking

Lovely 2 Bedroom Unit with Free Parking

Paintsville KY
Get rates
Book a stay at this golf apartment in Paintsville. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Johnson County Public Library and Mayo Mansion are located nearby.
Kitchen
Free WiFi
Best Western Plus Louisa

Best Western Plus Louisa

2.5 out of 5
18199 Highway 23 Louisa KY
Free Cancellation
Reserve now, pay when you stay
$95 nightly
The price is $105 total per night
$105 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
This hotel features an indoor pool and a gym. Enjoy the hot tub and free perks like full breakfast and free self parking. A business center, free WiFi in public areas, and a grocery/convenience store are also on offer.
Comfort Suites Prestonsburg West

Comfort Suites Prestonsburg West

2.5 out of 5
51 Hal Rogers Dr Prestonsburg KY
Free Cancellation
Reserve now, pay when you stay
$101 nightly
The price is $115 total per night
$115 total
Dec 28 - Dec 29
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
Pool
Breakfast included
Don't see what you're looking for?
See all available properties in Paintsville
View all properties
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.

Popular places to visit

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 Country Club

3.5/5(8 reviews)

Enjoy a round of golf in Paintsville at Paintsville Country Club. Take in the live music and mountain views in the area.

Paintsville Country Club

Preston Park

Explore the great outdoors at Preston Park, a lovely green space in Paintsville. Stroll along the marina or discover the mountain views in this family-friendly area.

Preston Park

Frequently asked questions

How much are vacation packages to Paintsville?
Treat yourself to a memorable travel experience in Paintsville with a vacation package starting at just $469. Reserving hotels, tours and flights through Travelocity is a piece of cake. What's more, our vacation deals will leave you with more money in your pocket for plenty of fun activities.
How long should my Paintsville vacation be?
Many visitors pack their bags and vacation in Paintsville for an average of 2 nights. That gives you a rough guide, but don't let it limit you. Whether you just stay a few nights to see the famous sights or linger a while to uncover hidden gems, an amazing getaway awaits.
Where can I get the best vacation package deals for Paintsville?
You'll come across a tempting selection of Paintsville package deals on Travelocity. With as many as 400 airlines and 1,000,000 properties around the globe, piecing together your ideal vacation will be a piece of cake.
Why should I purchase my Paintsville vacation bundle via Travelocity?
Nothing beats the satisfaction of knowing you've just bagged the best deal available — that's our Price Match Guarantee. Add to that our incredibly broad range of destinations and 24/7 team of customer service professionals and you've got the formula for a hassle-free vacation.
Can I save money on my Paintsville car rental if I book it with hotels and flights?
Absolutely — combine your car, hotel and flight into a Paintsville vacation package and you'll save a tidy sum. With so many places to explore in the Paintsville area, having your own set of wheels will make it easy to explore. Once you've buckled yourself in, get out on the wide open road and head to Paramount Arts Center, a well-known sight approximately 45 mi from Paintsville.
Which airport is best for Paintsville?
The main airport servicing Paintsville is Tri-State Airport (HTS). It sits 40 mi south of the city center.
What is there to do in Paintsville?
While veering off the tourist trail is no doubt rewarding, you really shouldn't miss the big-name attractions that make a destination famous. U. S. 23 Country Music Highway Museum and Paintsville Country Club are a couple of them in Paintsville.
Where should I stay when visiting Paintsville?
Many people choose to stay at the Ramada Hotel & Conference Center by Wyndham Paintsville. It's a terrific base for your Paintsville vacation.

Photos of local treasures

Browse Paintsville vacation photos for more inspiration

Explore More Ways to Travel with Travelocity