Vacation 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

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!

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!

Indian Run Cottage • Flatwoods KY

Enjoy the perfect blend of comfort, privacy, convenience, and modern style in this 3 bedroom 2 bathroom home just minutes from shopping and dining in Flatwoods KY. Featuring a beautiful kitchen with breakfast bar, upgraded appliances and furnishings, and clean, cozy beds. This home includes a dedicated work space with sleeper sofa and the full dining table seats four. Step outside to your private backyard and patio, perfect for morning coffee, evening drinks, or simply enjoying the fresh air!

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.

Private Accomodations in Historic Boneyfiddle

Enjoy Portsmouth Ohio's Boneyfiddle Historic District! Stay within walking distance of restaurants, events, shopping, and Shawnee State University. This is a fully furnished 1 bedroom/1 bath apartment with a private entrance. The nearly 1000 sq. ft. space boasts a galley kitchen open to the living room where the couch pulls out to a queen bed. Bedroom features include a king bed and walk-in closet. Washer and dryer access are on premises. This is a smoke-free unit. Pet-friendly.

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.

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

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.

Modern River-View Loft in Historic Boneyfiddle

Modern 3rd-floor loft in Portsmouth’s Historic Boneyfiddle District! Enjoy exposed brick, high ceilings, and a full kitchen with large island—perfect for cooking or gathering. Relax in the open living space with river views and plenty of natural light. Walk to riverside parks, local eateries, shops, and cafés along 2nd Street. Stylish, comfortable, and close to Shawnee State University.

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.