Holiday rentals in Greenup County

Home w/a River & Bridge view, a HotTub & an Igloo

RIVERTIME - A house w/a hot-tub & an igloo. Experience it all on the bank of the Ohio. The views are magical & soothing to the soul. Make your way into the backyard & you will quickly forget that you are in an Eastern KY residential area. It’s often stated by our guests that the view rivals some of the top landscapes & city skyline from around the world. You can walk to downtown Russell & enjoy shopping, great food & tasty drinks. Only a few mins from Ashland KY & 20 mins to Huntington, WV

Greenbo Lake Cabins-Fox Den

Welcome! Take it easy at this unique and tranquil getaway. On a 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!

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.

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!

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.

Large pet-friendly loft: walk to murals & dining

Occupying the entire second floor of a historic building, our loft is a blend of 19th-century architecture and modern comfort. Enjoy high ceilings and transom windows and the original exposed brick. Love to travel with pets? We are a pet-friendly space and welcome your furry friends. Since we are located on 2nd Street in the Historic Boneyfiddle District, you are within walking of distance of Shawnee State University and local shops and restaurants.

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

Beaver Lake

Welcome to the farm! Step inside to find a modern farmhouse, that balances open gathering spaces with cozy nooks. Fully equipped kitchen, luxury bedding and high speed WiFi. Spacious room for indoor and outdoor entertaining. We have thought of everything, so you don’t have to. Tucked away on 200 acres of secluded comfort and serene privacy. Nestled at the end of a private drive, surrounded by a park like setting. It’s truly a hidden gem.

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, 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.

Cozy, comfy and private-2 miles from the Casino

Cozy, Country setting. Very neat and clean 2 bedroom apartment with two queen beds. Country feel but close to all the necessities. You have the property to yourself and there's lots of parking. You are just minutes from Walmart, Dollar General, fast food and local restaurants. This property is just 15 minutes from Rush Off Road with easy parking for trucks and trailers.

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.