Vacation rentals in Greenup County

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Top-rated vacation rentals in Greenup County

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
The exterior of Pink Dreams Cottage is adorned with soft pink brick and floral decorations, creating a welcoming entrance. A pink door is framed by elegant lighting and a floral wreath. The charming sign displays the cottage's name, set against a manicured garden.
Home in Portsmouth
4.98 out of 5 average rating, 94 reviews

Pink Dreams Cottage: Hot Tub, Fire Pit, BBQ & More

Welcome to Pink Dreams Cottage – a one-of-a-kind, fully renovated pink paradise! This gorgeous cottage was lovingly transformed by a father & daughter duo from an abandoned house to a picturesque pink cottage that’s perfect for your next getaway. Whether it’s a special occasion, a girls weekend, a romantic getaway, or a creative escape, this is the perfect place to make memories that will last a lifetime. Come experience the magic of Pink Dreams Cottage and make your pink dreams come true!

Top guest favorite
The exterior of the remodeled home is presented, showcasing a blend of modern white siding and a wooden porch with an inviting overhang. Lush greenery surrounds the property, complementing the bright blue sky and scattered clouds above.
Home in Wheelersburg
4.96 out of 5 average rating, 54 reviews

Visit The Sage Door House

This remodeled home in Wheelersburg is the perfect peaceful retreat, nestled on a quiet dead-end street. The serene backyard offers an ideal space for relaxation, where you can unwind and enjoy nature. The outdoor space provides a lovely spot for relaxing, while the fire pit on the patio offers a cozy setting for delightful outdoor experiences. Whether you're looking to relax during the day or enjoy an evening under the stars, this home offers a perfect blend of comfort and tranquility.

Guest favorite
A spacious exterior view of a two-story home surrounded by lush greenery. The brick and stone facade is complemented by red accents and multiple windows, allowing natural light to fill the interior. A manicured lawn extends in front, offering a welcoming entrance.
Loft in Ashland
5 out of 5 average rating, 18 reviews

The Haven:Homey Loft in Cozy, Quiet Spot

Take it easy at this unique & tranquil getaway. This spacious, fully furnished 1-bedroom apartment & full kitchen is for traveling professionals, tourists, or a quick get-a-way for some rest & relaxation providing comfort, privacy, & convenience while in Ashland, KY. Enjoy a home away from home offering 1 queen bed, 1 full bed, workspace, cozy living room w/ smart TV & prime subscription, a breezeway with table, relaxing hammock chair, cafe lights, outdoor music available, & pretty views.

Top guest favorite
A comfortable living area features a dark sectional sofa and two reclining chairs. A wooden coffee table is centered on a patterned area rug. Natural light enters through a window with wooden blinds, while a television rests on a side table opposite the seating arrangement.
Home in Raceland
5 out of 5 average rating, 68 reviews

Cozy house located in the woods

It may feel like the country, but it's only 5 miles from Ashland KY and 20 minutes from Shawnee State University. Plenty of parking if you plan on visiting Rush Off Road which is just 20 miles away! If you want to try and hit it big at Sandy's casino you are only 13 miles away! Wake up to deer in the yard and enjoy a cup of coffee or a relaxing dinner on your beautiful deck with screened in sunroom. Our home is across the street so if you need anything during your stay let us know!

Top guest favorite
Guest suite in Ashland
4.99 out of 5 average rating, 165 reviews

Cozy, newly remodeled, extra large 2 bdrm basement

Beautiful home in a very nice, quiet neighborhood. Close to downtown Ashland (3 miles) and I-64 (5 miles). This is a full size newly remodeled basement with it's own outside entrance. Great host and great setting. Access to the beautiful back yard, kids gym, gazebo, grill and covered patio. The basement has large windows in the bedrooms and queen beds. Located 8 minutes from King’s Daughters Hospital and 30 minutes from Huntington, WV hospitals. Long term travel workers welcome.

Top guest favorite
Home in Greenup
5 out of 5 average rating, 37 reviews

Victorian Home in Greenup

Whether you are traveling alone or with the whole family, this great place built in 1870 has been completely re-done with lots of room for fun. Enjoy all the comforts of home and explore all that Greenup has to offer within walking distance. There are several festivals including Old Fashion Days, the county fair and spectacular 4th of July fireworks. The city also has a great library with a large genealogy section, a city park with a pickleball court and a boat ramp for river access.

Top guest favorite
A well-equipped kitchen features light-colored cabinetry and a modern sink, with a stainless-steel dishwasher below. Natural light enters through a large window above the sink, and decorative pendant lights enhance the space. The tile floor displays a geometric pattern for visual interest.
Cottage in Portsmouth
5 out of 5 average rating, 83 reviews

Private, safe, and quiet Cottage at Walnut Hill

Enjoy a peaceful experience at this conveniently located cottage that is situated in the hilltop area of Portsmouth as part of a ten acre, wooded property. It has off street parking and sits on a safe and secluded property where you can enjoy nature and deer watching from the lovely back porch. It's located a few minutes from our local hospital (SOMC) and is convenient to everything Portsmouth has to offer. We maintain the highest cleaning standards!

Guest favorite
Cabin in Garrison
4.92 out of 5 average rating, 65 reviews

Third Hollow Farm

Escape to privacy just 1 hour from Ashland, Maysville & Morehead, KY. Tucked away on 400 private acres, this secluded farm stay sleeps 6 comfortably — perfect for couples, friend groups, or a quiet work retreat. Strong Wi-Fi keeps you connected, while wide-open skies and fire pit evenings help you truly unwind. Perfect For: • Girls weekends • Family reunions • Birthday weekends • Couples traveling together • Wedding guest stays • Small retreats

Guest favorite
The living area features a welcoming orange accent wall with a decorative sign and a lamp on a side table. A dark sofa with patterned cushions faces a circular coffee table. A dining area is visible in the background, illuminated by natural light from a nearby window.
Cabin in Greenup
4.98 out of 5 average rating, 122 reviews

White Oak 2-bedroom cabin along the Little Sandy

Relax with the whole family or a few friends in our off the beaten path cabin nestled along the Little Sandy River. Bring a kayak or some fishing gear and enjoy the quiet seclusion of The White Oak Cabin. You are surrounded by the wilderness but still close enough to take the family out for a movie.

Guest favorite
A modern kitchen area features a spacious granite countertop with seating for four black metal chairs. Stainless steel appliances are visible, along with a microwave and dining necessities. Natural light fills the space through two windows, complementing the neutral decor and inviting ambiance.
Home in Portsmouth
4.92 out of 5 average rating, 144 reviews

Fresh Remodel Modern-Home Walking Dist. 2 Hospital

Freshly Remodeled Home. Modern decor and features. Enjoy this cozy home, walking distance to the hospital and a short drive to restaurants & the heart of historic downtown Portsmouth. Note: Guests will have Street Parking in front of the home.

Top guest favorite
Camper/RV in Ironton
5 out of 5 average rating, 20 reviews

Time to glamp

Reconnect with nature at this unforgettable escape. Avoid the hustle and bustle of town by staying out in the country. Whether you are in town for work or looking for a place to just step away and enjoy Southern Ohio, we have you covered.

Top guest favorite
A spacious gray house is set against a lush green hillside. A large wooden deck extends from the front, providing outdoor space for relaxation. Nearby, a mature tree offers shade, and the surrounding grass is well-maintained, contribute to a serene rural environment.
Cottage in Wheelersburg
4.96 out of 5 average rating, 233 reviews

Safe Quiet Country getaway. Inside city limits.

Bring the whole family to this great place with lots of room.

Popular amenities for Greenup County vacation rentals