Paintsville Holiday Rentals from NZ$221: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Paintsville has to offer?

Hidden Acres Escape: A Bluegrass Retreat : This holiday home rental outside of Paintsville is located in a rural location, and has an indoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and an arcade/games room so that you can immerse yourself in your holiday.

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Our top choices for Paintsville holiday rentals

A large, historic house with a prominent turret, a fountain, and a well-maintained lawn.

1. Private 2BR Renovated Guest Suite in Historic Home with Kitchen

Paintsville

includes taxes & fees

26 Oct - 27 Oct

A wooden deck with a mailbox, surrounded by a wooden fence, leading to a shed with a window.

2. NO RV? NO PROBLEM! STAY IN OUR FAMILY-FRIENDLY, COZY COTTAGES.

Staffordsville

Becky M.

includes taxes & fees

26 Oct - 27 Oct

A kitchen with a built-in oven, microwave, and stainless steel range.

3. Cozy Home in Heart of Prestonsburg

Prestonsburg

Ashleigh g.

includes taxes & fees

27 Oct - 28 Oct

A rustic cabin surrounded by lush greenery and a fenced area.

4. The Boons Camp Cabin

Boons Camp

includes taxes & fees

28 Oct - 29 Oct

A rustic cabin with a porch, surrounded by lush greenery and trees.

5. Workman's Wildlife Haven, Secluded country setting vacation cabin

Louisa

Steven S.

includes taxes & fees

11 Nov - 12 Nov

A dining area with a wooden table, two chairs, a vase with a plant, a wall clock, and a door with a window.

6. Cozy Tiny Home Quiet 1/1 Close to Riding Trails

Martin

Kimberly H.

includes taxes & fees

2 Nov - 3 Nov

A hot tub with seating and a table, surrounded by a wooden deck and trees.

7. The Mountain Magnolia Hot tub on private deck

Inez

Gavin L.

includes taxes & fees

25 Oct - 26 Oct

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Top Paintsville Hotel Reviews

Best Western Plus Louisa

8/10 Good

"Absolutely the warmest cleanest pool I’ve ever been in! Hot tub was also very relaxing. Only down fall was the carpets being a tad on the run down side. Other than that it was a great stay and I would stay again."

Spark by Hilton Prestonsburg

10/10 Excellent

"I really appreciated the staff's great attitude all during the stay. I checked in without issue then later in the evening realized TV was not working so they facilitated me moving to a different room. As I was checking out, the lady at the desk worked with me for a second reservation that went flawlessly."

Charming 2-bedroom cabin + loft in fabulous Salyersville with AC and WiFi

10/10 Excellent

"Amazing, secluded, cozy place. Very easy to relax and just chill. Even a surprise to find there was a fire pit, as we weren’t expecting bcuz wasn’t listed in amenities. We really enjoyed our time."

Hidden Acres Escape: A Bluegrass Retreat

10/10 Excellent

"CHOOSE THIS PROPERTY!! GORGEOUS property nestled in the peaceful hills of Kentucky! The home is wonderful for hosting a large crew with plenty of space for kids! All amenities are very clean and fully functioning! Host provides plenty of toiletries etc. so you can pack light! Huge pool and relaxing hot tub were also amazing! We will definitely stay here again next time we’re in the area! Thank you for an amazing stay!"

Find out more about Paintsville

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Paintsville holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Paintsville. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Paintsville. Seeing all the best attractions is bound to make you fall in love with Paintsville. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Paintsville short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Paintsville?

Yes, there are holiday rentals in Paintsville close to U. S. 23 Country Music Highway Museum, or you can select a more secluded option if you're looking for a relaxing stay. Paintsville is known for its mountain views and monuments. Make sure you have time to check out the golf courses and waterfront during your trip.

What are some of the best holiday rentals that Paintsville has to offer?

Hidden Acres Escape: A Bluegrass Retreat: This holiday home rental outside of Paintsville is located in a rural location, and has an indoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and an arcade/games room so that you can immerse yourself in your holiday.

What’s there to see and do in Paintsville?

Preston Park and Swamp Branch Trailhead are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include U. S. 23 Country Music Highway Museum. Mayo Mansion and Johnson County Public Library are other places to visit while you're in town.

What’s a holiday rental in Paintsville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Paintsville. Holiday rentals offer amenities like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a family trip.

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Check prices for these dates

Our top choices for Paintsville holiday rentals

1. Private 2BR Renovated Guest Suite in Historic Home with Kitchen