Holiday rentals in Grayson

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!

Sky Loft on 10 . 2 bed . 2 bath + Modern luxuries

Lay your head in the clouds. Sky Loft on 10 is a brand new, state-of-the-art loft furnished with modern luxuries. It is conveniently located in the center of the city blocks away from downtown, Paramount Arts Center, KDMC, Central Park and the Ashland Town Center Mall. Tenth floor views and access to two private balconies provide stunning views of the city, riverfront and Tri-State area. Perfect for hosting or a relaxing getaway. Your next stay, retreat or celebration is just on the horizon.

Cliffside Properties / Carter Caves Cabin Rental

Perched on the edge of the canyon at the entrance to Carter Caves State Park, our 3-story cabin easily sleeps 10. On our twenty acre preserve, there are 5 cave entrances and two caves that open into the State Park gorge, with many box canyons and waterfalls to explore. Whether you're enjoying the State Park's massive natural bridges, cave tours, horseback riding, swimming, fishing or kayaking on Smoky Lake or Tygarts Creek, our Cliffside Cabin rental is a great place to relax and explore.

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.

Cabin at Cabin Creek Campground

Private cabin located in campground close to bathhouse. A/C and electric fireplace. Porch swing, fire ring, & picnic table for your outside enjoyment. Queen size bed with full size bed in loft overhead. Microwave & small refrigerator. Dining table with 3 benches. Comfortable sitting chair with footstool. Fishing included in our 12-acre lake. Walking path runs the length of the campground. Bring bed linens (sleeping bag or blanket/sheet) & pillow, bath linens (towels/washcloths).

First floor apartment near antique shops

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.

Buster's River Retreat

Welcome to the River! We are thrilled to have you as our guest and hope you have a comfortable and enjoyable stay. This cozy house is designed to offer you a relaxing retreat. You'll find everything you need to feel at home, from a fully-equipped kitchen, high-speed Wi-Fi and plush bedding. If you’re here for work, the desk in the bunk room should meet all your needs. Relax on the back deck and watch the barges go by on the mighty Ohio River or play some ping pong in the game room.

Roosevelt Retreat II - 1BR Queen/1BA

Keep it simple at this peaceful 1 queen bedroom, 1 bath home with a sofa in the living room. The kitchen is furnished with a full size refrigerator, stove, and fully stocked coffee bar. This quiet, private home is 1 of 2 on the property and it is located at the back of the property. There are 2 flat screen TV’s in the bedroom & living room with high speed wifi. You will enter in the alley behind the house with 1 car parking available right outside your door. *** PET FEE APPLIES***

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

Private A-Frame on 20 Acres | Remote-Work Friendly

Solstice Haven is a secluded A-frame cabin set on 20 private acres in Peebles, Ohio, designed for guests who want peace, privacy, and productivity. Whether you’re escaping the city, working remotely, or staying to recharge, this property has everything you need to feel refreshed. Surrounded by woods, private hiking trails, and a soaking tub, this cabin combines deep nature and modern comforts. High-speed WiFi makes it ideal for weekday stays, long weekends, and extended visits.

Rush Retreat

Come to enjoy in Rush Ky , Two miles from Rush of Road Park on the Same road. Our guest will have enough parking for a Truck , Trailer and Atvs , drive around the neighborhood is safe and relax. We include all the amenities with a Full kitchen with all you need ready to cook with what you need , full bathroom amenities , all linen , wifi , smart Tv. !Just bring your bags . Plenty of space to park your ATVs and trailers , safe environment. 15 miles from Ashland

Cozy and Private - Long Bottom Cabin

The perfect peaceful family getaway! Experience the beautiful hills of Kentucky. Enjoy listening to the birds especially the Whippoorwills. Roast hotdogs and S’mores on the fire while gazing at the stars. You may experience some wild life, too! Private and quiet. Traveling US 23 or I64? It’s a great stopping place. 10 miles to Rush Off Road 22 miles to The Paramount Arts Center 15 miles to Camp Landing Entertainment District 23 miles to Yatesville Lake