Paintsville Vacation Packages 2026 from $552

Paintsville flight + hotel vacation packages

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

Shaker Village of Pleasant Hill

Shakertown

$552

per person

Nov 13 - Nov 15

found 1 day ago

Roundtrip non-stop flight included

Charleston (CHS) to Lexington (LEX)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the 6 conference rooms, along with express check-out. A restaurant, a 24-hour front desk, and wedding services are also provided.

21c Museum Hotel Lexington

Downtown Lexington

$750

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip non-stop flight included

Charleston (CHS) 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.

Elwood Hotel & Suites

$791

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip non-stop flight included

Charleston (CHS) to Lexington (LEX)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A lobby fireplace, express check-out, and dry cleaning are also on offer.

Springhill Suites by Marriott Lexington Fritz Farm

$705

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip non-stop flight included

Charleston (CHS) to Lexington (LEX)

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Origin Lexington a Wyndham Hotel

$794

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip non-stop flight included

Charleston (CHS) 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.

Top Paintsville hotels deals

Days Inn by Wyndham Paintsville

512 S Mayo Trail Paintsville KY

Free Cancellation

Reserve now, pay when you stay

$72 nightly

$80 total

Oct 5 - Oct 6

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive 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

Pet friendly

Ramada Hotel & Conference Center by Wyndham Paintsville

624 James Trimble Blvd Paintsville KY

Free Cancellation

Reserve now, pay when you stay

$118 nightly

$130 total

Oct 11 - Oct 12

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

Budget Inn Express

709 S Mayo Trail Paintsville KY

$73 nightly

$80 total

Oct 16 - Oct 17

Total with taxes and fees

Free self parking is available and the motel's front desk is staffed around-the-clock. Laundry facilities are provided for your convenience.

Pet friendly

Parking included

Modern Small-Town Living

Paintsville KY

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This apartment features laundry facilities.

Washer

Dryer

Private 2BR Renovated Guest Suite in Historic Home with Kitchen

Paintsville KY

$391 nightly

$431 total

Oct 19 - Oct 20

Total with taxes and fees

This apartment features laundry facilities.

Kitchen

Washer

Downtown Paintsville Vacation Rental!

217 3rd St Paintsville KY

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Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.

Kitchen

Parking included

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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)

You can learn about the history of Paintsville with a visit to Walking Bridge. Discover the area's mountain views and countryside.

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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 $552. 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.