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.

Clarion Hotel Conference Center Lexington North

CA $709

per person

Mar 31 - Apr 5

found 1 hour ago

Roundtrip flight included

Detroit (DTW) to Lexington (LEX)

7.6/10 Good! (1,002 reviews)

Clean room, nice staff.

Reviewed on Feb 3, 2026

21c Museum Hotel Lexington

Downtown Lexington

CA $864

per person

Mar 31 - Apr 5

found 1 hour ago

Roundtrip flight included

Detroit (DTW) to Lexington (LEX)

8.8/10 Excellent! (1,002 reviews)

Great hotel in great location. Clean, modern, and artsy. Room was very comfortable and the shower was great, which is big for me. It had good water pressure with hot water. Check in and out was quick and easy.

Reviewed on Jan 20, 2026

DoubleTree Suites by Hilton Hotel Lexington

CA $959

per person

Mar 31 - Apr 5

found 1 hour ago

Roundtrip flight included

Detroit (DTW) to Lexington (LEX)

8.8/10 Excellent! (1,002 reviews)

Room was spacious! Staff was great! Amenities. Great cookies!!!

Reviewed on Feb 2, 2026

Home2 Suites by Hilton Lexington University / Medical Center

Zandale

CA $899

per person

Mar 31 - Apr 5

found 1 hour ago

Roundtrip flight included

Detroit (DTW) to Lexington (LEX)

8.8/10 Excellent! (1,000 reviews)

Room, service and breakfast were excellent, but a lot of kids-teenagers making a lot noises running everywhere in the corridors (3rd floor, at least) up to 12 midnight, help putting some restrictions in writing but nothing was around. I complained about but nothing (at the front desk-call) a male answer; I complained again around 11:30-12pm and female answer and this time she when to check, she did a great job for both sides.

Reviewed on Jan 5, 2026

Country Inn & Suites by Radisson, Lexington, KY

CA $791

per person

Mar 31 - Apr 5

found 1 hour ago

Roundtrip flight included

Detroit (DTW) to Lexington (LEX)

8/10 Very Good! (1,001 reviews)

Staff was kind. Room was clean and there were plenty of towels. The wood furniture and walls have taken a beating. Lots of wood chips and the walls were painted white but there was a ton of paint drops on the floor and other places that didn’t require white paint. Bedding was white and clean. Tile floors, good TV and cable channels.”

Reviewed on Feb 4, 2026

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Paintsville Hotel Deals

Ramada Hotel & Conference Center by Wyndham Paintsville

624 James Trimble Blvd Paintsville KY

Fully refundableReserve now, pay when you stay

CA $148

CA $163 total

Feb 15 - Feb 16

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

Days Inn by Wyndham Paintsville

512 S Mayo Trail Paintsville KY

Fully refundableReserve now, pay when you stay

CA $93

CA $103 total

Feb 9 - Feb 10

includes taxes & fees

7.6/10 Good! (516 reviews)

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

Reviewed on Jan 23, 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.