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.
Montgomery Inn BnB

Montgomery Inn BnB

4 out of 5
Price was $1,123, price is now $977 per person
$977
per person
Oct 1 - Oct 7
found 1 day 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 $1,495, price is now $1,244 per person
$1,244
per person
Oct 1 - Oct 7
found 1 day 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.
Elwood Hotel & Suites

Elwood Hotel & Suites

4 out of 5
Price was $1,272, price is now $1,130 per person
$1,130
per person
Oct 1 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) 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.
DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

4 out of 5
Price was $1,426, price is now $1,276 per person
$1,276
per person
Oct 1 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Lexington (LEX)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free WiFi and a free airport shuttle. Self parking, a business center, and a coffee shop are also offered.
Beautiful House in Nicholasville

Beautiful House in Nicholasville

2 out of 5
Save 100% on your flight
Price was $3,677, price is now $3,300 per person
$3,300
per person
Oct 1 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Lexington (LEX)
Free WiFi in public areas is available at this vacation home.

Top Paintsville hotels deals

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
$72 nightly
The price is $80 total per night
$80 total
Aug 4 - Aug 5
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

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
$118 nightly
The price is $130 total per night
$130 total
Aug 9 - Aug 10
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
Private 2BR Renovated Guest Suite in Historic Home with Kitchen

Private 2BR Renovated Guest Suite in Historic Home with Kitchen

Paintsville KY
Get rates
This apartment features laundry facilities.
Kitchen
Washer
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
Comfort Suites Prestonsburg West

Comfort Suites Prestonsburg West

2.5 out of 5
51 Hal Rogers Dr Prestonsburg KY
Free Cancellation
$110 nightly
The price is $124 total per night
$124 total
Aug 23 - Aug 24
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
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
$108 nightly
The price is $119 total per night
$119 total
Aug 31 - Sep 1
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.
Pool
Hot Tub
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.

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 are vacation packages to Paintsville?
Treat yourself to a memorable travel experience in Paintsville with a vacation package starting at just $977. 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

A steel bridge spanning a river, surrounded by dense forest and hills.
An aerial view of a town with a mix of residential and commercial buildings, surrounded by green hills.

Explore More Ways to Travel with Travelocity