Holiday rentals with outdoor seating 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!

Sandyville- A Riverside Retreat!

Cozy stay on the Little Sandy River, this cabin is a perfect place for your next friend vacation or couples retreat! Minimally furnished but with everything you need to enjoy a cup of coffee and head outdoors. All cabin rooms share a porch & access to the open area under cabin where simple meals can be fixed. Each room has its own bathroom with shower. Backyard has a split level dock right on the river. Towels & linens provided. 2 Kayaks available with rental. Message us with PFD sizes needed.

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!

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.

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.

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

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.

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. Kayaking & hunting also available. Perfect For: • Girls weekends • Family reunions • Birthday weekends • Couples traveling together • Wedding guest stays • Small retreats

Riverside Cottage

15 min from SOMC & KDMC. Enjoy this cozy 2-bed/1-bath cottage along the scenic Ohio River with beautiful views, a covered porch for morning coffee, and everything you need for a comfortable stay. Whether you’re in town for work, an event, or passing through, this riverside cottage offers a convenient place to stay. Located next to a local event venue, it’s a great option for wedding guests, event attendees, traveling professionals, or anyone visiting “The River House” Venue.

Private, safe, and quiet Cottage at Walnut Hill

Enjoy a peaceful experience at this conveniently located cottage that is situated in the hilltop area of Portsmouth as part of a ten acre, wooded property. It has off street parking and sits on a safe and secluded property where you can enjoy nature and deer watching from the lovely back porch. It's located a few minutes from our local hospital (SOMC) and is convenient to everything Portsmouth has to offer. We maintain the highest cleaning standards!