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

Greenbo Lake Cabins-Deer Haven

Welcome! Take it easy at this unique and tranquil getaway. Private country setting, located next to Greenbo Lake State Park, where you can take advantage of many outdoor activities including hiking, boating, fishing and swimming. Nearby entertainment facilities: Riverbend Golf Course, Paramount Arts Center, Portsmouth Motor Speedway, Huntington Civic Center, Sandy’s Racing and Gaming and Malibu Jack’s Indoor Family Theme Park. Experience Ky wildlife freely roaming, right next to your cabin!

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.

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!

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.

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.

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.

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.

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.