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.

Courtyard Lexington Keeneland/Airport

Beaumont Residential

CA $1,229

per person

Apr 10 - Apr 13

found 3 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Lexington (LEX)

8.8/10 Excellent! (796 reviews)

The staff is very friendly. Rooms are very clean. Located in safe, convenient area.

Reviewed on Nov 11, 2025

21c Museum Hotel Lexington

Downtown Lexington

CA $1,357

per person

Apr 10 - Apr 13

found 3 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Lexington (LEX)

8.8/10 Excellent! (1,002 reviews)

Clean room. Great staff. Restaurant was delicious.

Reviewed on Feb 15, 2026

The Sire Hotel Lexington, Tapestry Collection by Hilton

Downtown Lexington

CA $1,586

per person

Apr 10 - Apr 13

found 3 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Lexington (LEX)

9.4/10 Exceptional! (838 reviews)

I have stayed there several times. Always enjoyable. Clean and friendly.

Reviewed on Feb 4, 2026

Residence Inn Lexington Keeneland/Airport

Beaumont Residential

CA $1,248

per person

Apr 10 - Apr 13

found 3 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Lexington (LEX)

9/10 Wonderful! (560 reviews)

It was great everything was so clean and the staff was awesome and the lady who makes the breakfast omg she did amazing

Reviewed on Feb 15, 2026

Fairfield Inn & Suites Lexington Keeneland Airport

Beaumont Residential

CA $1,235

per person

Apr 10 - Apr 13

found 3 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Lexington (LEX)

8.8/10 Excellent! (702 reviews)

Change of management cost me over $200. I should’ve been informed so I could have found a different location!!!

Reviewed on Jan 17, 2026

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Paintsville Hotel Deals

Days Inn by Wyndham Paintsville

512 S Mayo Trail Paintsville KY

Fully refundableReserve now, pay when you stay

CA $93

CA $102 total

Feb 18 - Feb 19

includes taxes & fees

7.6/10 Good! (520 reviews)

Everything worked. Didn’t stink. Simple classic cozy room.

Reviewed on Jan 23, 2026

Ramada Hotel & Conference Center by Wyndham Paintsville

624 James Trimble Blvd Paintsville KY

Fully refundableReserve now, pay when you stay

CA $150

CA $166 total

Mar 1 - Mar 2

includes taxes & fees

8.8/10 Excellent! (556 reviews)

The room was very clean and staff was very nice .we were there during a witer storm and the only thank was restaurant was clise and only had breakfast on Saturday morning but we found other places close by to eat .but the staff was very friendly and helpful housekeeping was also helpful and ...

Reviewed on Jan 26, 2026

Downtown Paintsville Vacation Rental!

217 3rd St Paintsville KY

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See all 59 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.