Holiday rentals in Grayson

The Roundabout Retreat

Circle back to the "The Roundabout Retreat," a delightful 3BR home a heartbeat away from UK King's Daughter Medical Center. Perfect for families, this gem features a chef-ready kitchen, private fenced yard, plush king bed in a large master, new 58" TVs, office space, and a quaint dining room. Enjoy the convenience of our LG Washtower, a selection of board games for fun evenings, and decor that’s both elegant and welcoming. Your tranquil downtown haven melds style and convenience beautifully.

The Cozy Cabin

Our "Cozy Cabin" getaway is located in a peaceful country setting. A creek & hillside is located behind the cabin. Relax on our 2 porches and enjoy the view of our field with horses grazing and deer passing thru. There is a fire pit, gas grill & small shelter house with swing for your outside enjoyment. All the amenities for a relaxing stay close to Yatesville Lake (18 miles), Rush Off-Road Park (13 miles) & Giovanni's Pizza (5 miles). Tristate area KY/WV/OH can be in all within 30 minutes.

Spacious Family Home w/ Fireplace & Fire Pit

Kennedy House is a lovely home located in Grayson, KY. Sparkling clean and containing lots of homey touches, you'll find this the perfect place to gather with family and friends. On the main level, there is a fully furnished kitchen, a dining room, a cozy living room with a fireplace (bring your own wood), a master bedroom/bathroom, another bedroom with two single beds, and a full bath. Upstairs there is a bedroom with two queen beds, a full bathroom, and a spacious play and reading area.

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.

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, 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).

Luxury Cliffside Hammock House

Escape to a modern luxury hammock oasis: with cozy indoor & outdoor loft-net hammocks, memory foam beds with MyPillow pillows for supreme comfort, and MyPillow towels enhancing the spa-like bathrooms featuring rainfall showers and body jets. Adventure awaits with a private trail into Daniel Boone National Forest, a hot tub, and a pool table. This space isn't just a stay but an experience, designed for those seeking luxury, comfort, and a touch of adventure. Not Suitable for children.

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

Creekside Haven Tiny Home Spring Dates Open!

Welcome to Creekside Haven! Tucked along a peaceful creek in Minford, OH, our cozy tiny home is the perfect getaway for couples, families, or traveling professionals looking for comfort and convenience. Relax by the fire pit, swing in the hammock, or unwind inside with all the comforts of home! Pets are welcome with prior approval. Please note we can only allow small dogs (under 30 pounds).

Boulder Brook Cabin

Wonderful cozy guest cabin in the woods. Knotty pine living space with outdoor elements throughout. Open concept with beds/living room/kitchen all sharing the same space. Full stocked kitchen with Kuerig coffee bar ready to start your day off right! Covered front porch for sitting and enjoying the views. Parking at front door.