Vacation rentals in Greenup County

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!

Third Hollow Farm

Escape to privacy just 1 hour from Ashland, Maysville & Morehead, KY. Tucked away on 400 private acres, our secluded cabin sleeps 6 comfortably — perfect for couples, friend groups, or a work retreat. Strong Wi-Fi keeps you connected, while quiet fire pit evenings help you truly unwind. Firewood & 4 kayaks included. Hunting available for an additional charge. Perfect For: • Girls weekends • Family reunions • Birthday weekends • Couples traveling together • Wedding guest stays • Small retreats

Country Farm House

Bring the whole family to this peaceful place with lots of room for fun. This Country Farm House features 5 bedrooms and two bathrooms and sleeps up to 15 people. Plenty of room to hold a family event/gathering. Relax and enjoy a peaceful getaway in a country/farm setting while watching the cows, wild deer and turkeys roam around the property. Full game room/play room in the basement equipped with movies, video games, board games, and ping pong table. Starlink WiFi throughout the house.

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.

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.

Mamaw's Place

Relax with the entire family tucked away in the foothills of the Appalachian mountains in the rolling hills of the Ohio River Valley. Enjoy the large front and backyard, pool, sunroom, and game room. Boat ramps that enter into the Ohio River and Kinniconick Creek (that leads to the river) are just a few miles away. You are within a 15 minute drive to gather any supplies/needed groceries. As owners we can be available for any issue or concerns within minutes.

RiverSuite1-Experience the view w/a group of 10+

Relax by the river in this beautiful space that showcases a huge living room with a panoramic view of the Ohio River & Bridge. Walkout onto the enormous, covered deck to relax while you take in the mesmerizing view. Located less than a 1/2 mile away from the Downtown (DTR) where you can stroll along historic brick streets as you dine and shop at several unique spots. The view is often said to rival the world’s most beloved views.

Charming Tiny Space/ Modern Minimalist

This unique place has a style all its own in a perfect tiny space. Snuggle into a perfect getaway or extended stay. Located in downtown Portsmouth within walking distance to Marting’s Event, Shawnee State University, Vern Riffe Performing Arts Center, Ohio River, Historic Boneyfiddle District with many antique shops and restaurants. Great place to jump on your bike and travel around. Wonderful things to do and see.

Riverfront Vineyard, Pool, Hot Tub, Guesthouse

Escape to Red Gate Farm & Vineyard, a peaceful 28-acre riverfront retreat in Quincy, Kentucky. Enjoy vineyard views, beautiful sunrises and sunsets, and a spacious cabin filled with warm, vintage-inspired charm. The cabin sleeps up to 12 guests. The charming Guest House, located just steps from the cabin, accommodates 4 additional guests, bringing the property's total overnight capacity to 16 guests.

4 beds + futon + cot, 8 guests

This is a quiet place at the end of the road, surrounded by 250 acres of private forest land. It is a nice place to come, relax, hike and enjoy the beautiful natural surroundings in eastern Kentucky. There are trails to hike and a pond for fishing. There are 2 bedrooms. Bedroom 1 has a queen size bed. Bedroom 2 has a bunkbed and a twin bed. The living room has a full-size futon that sleeps 2 adults.

The Chillicothe Street Loft

This centrally located loft on Chillicothe Street features a spacious open floor plan. Come and experience your overnight stay at this historic building. The loft is conveniently located near restaurants, shopping, Shawnee State University and Martings building. The loft is located on the second floor of the building which is only accessible by rear stairwell .

Bee's Place on the Beautiful Ohio River

A spacious and relaxing riverside getaway; your own upstairs private guest suite with keyless entrance equipped with a full bathroom, kitchen, and patio located on the beautiful Ohio River. You will have a private dock available for you to fish, lounge, and relax, as well as a marina less than 3 miles away to dock your boat in the evenings.