Holiday houses 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!

Value · Family · Layout

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

Family · Value · Cleanliness

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.

Family · Value · Accuracy

River & Bridge view - HotTub, CoolingTub & MistFan

Enjoy a hot-tub, cooling tub and misting fan during the summer. The river & bridge 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

Family · Value · Beach

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.

Family · Value · Nearby

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!

Location · Family · Amenities

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.

Family · Value · Indoor spaces

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.

Family · Value · Outdoor spaces

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.

Location · Family · Kitchen

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.

Location · Family · Outdoor spaces

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.

Family · Location · Barbecue

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.

Family · Location · Long stay