Vacation rentals in Eastern

The Eagle's Rest Country Cabin

Welcome to The Eagle's Rest! This family & pet friendly cabin is nestled just outside of Prestonsburg. Mountainous escapes of sunrises & sunsets. Enjoy family time w/a game room featuring a bar, billiard table, & dart board. Garage w/fire pit for entertaining or a small RV/Camper! Smart-Tv’s w/YouTubeTV & T-Mobile Int. Located near StoneCrest Golf Course. Put on your hiking boots for Jenny Wiley State Park, & Sugarcamp Mtn.Trails & Middle Creek Battlefield. Mountainous air & bird watching await.

Living The Dream

*If you book for 7 days or more, you will receive a 20% discount off your stay. Our home is perfect for your visit in Pikeville, especially for a large group. Enjoy the complete home with 3 bedrooms, 2 full baths, a complete kitchen with dishwasher, & washer/dryer. You'll enjoy a good nights sleep in a quiet space on high quality mattresses. We are located just down the street from a Food City. We have free WIFI & a Smart TV (NO CABLE TV). We’re a short 5 minute drive from downtown Pikeville.

Bear Creek Cabin • Vineyard Views & Fishing Pond

Escape to Bear Creek Cabin, overlooking the pond at MountainRose Vineyards. Enjoy peaceful porch views, modern comfort, and easy access to winery tastings, mountain trails, and quiet evenings under the stars. Perfect for couples, solo travelers, and small groups/families seeking a serene getaway. Fishing is allowed in the adjacent pond with a waiver signature. Must bring your own fishing equipment. Wine and charcuterie options can be pre-ordered to be waiting in the cabin for your arrival!

Robbie’s Rest: Amazing Mountaintop Sunrises

2020 new unit with nice deck, wonderful mountain scape with amazing sunrises from your deck or the deck of the main house where host lives. 8 acres that sit where the rolling hills meet the mountains overlooking the Daniel Boone Forest. 35 miles from Lexington, you will enjoy the peace & quiet of the beautiful mountains. Minutes away from the trails, waterfalls & attractions of Natural Bridge State Park & the Red River Gorge! We hope you will visit us soon! *Sunrise is not always visible

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.

The Shotgun House

Enjoy your stay at the Shotgun house located in the heart of Prestonsburg within walking distance to a popular restaurant and downtown shopping. This cozy house offers a 58" TV and playstation in the living and also a 50" TV in the bedroom. Relax outside on a covered porch and enjoy the occasional local live music. Located close to the Prestonsburg Passage Trail, Mountain Arts Center, Middle Creek National Battlefield, Pikeville Exp Center and a short drive to the Red River Gorge.

Cliffside Romantic Retreat LOVE

Fall in love at the unique and serene "Tis So Sweet Cliffside Cabin". The space is designed for a lovers retreat with luxuries of a spa bathroom, massage chair, fire table, recliner seat hot tub, and much more! This newly built cabin is peacefully secluded, yet still only a few miles away from the Natural Bridge State Park, Red River Gorge, Daniel Boone National Forest, underground kayaking, zip lines, rock climbing, swimming, delicious food and many other local attractions.

Cowan Creek Cottage

Cowan Creek Cottage is close to the Cowan Community Center and only 5½ miles outside the city limits of Whitesburg. The cottage is located at the foothills of Pine Mountain. You’ll love the cottage and enjoy the feel of having your own little home in the mountains. Enjoy a clean and comfortable home away from home while visiting friends and family and enjoying our community. Cowan Creek Cottage is good for couples, solo adventurers, business travelers, and families.

Spacious 3 bedroom cabin with hot tub

Located in Paintsville, Kentucky. Gather around the wood fireplace and enjoy a game of pool. There are 2 smart tv's to binge your favorite shows on. Or unplug and and take in the sights on the wrap around porch with a good book. Enjoy the outdoor kitchen and firepit, then hop in the 8-person hot tub. located just 5 minutes from hiking trails, Paintsville lake state park and golf course, and local eateries . Walmart is conveniently only 8 minutes away.

Premium A-Frame • Hot Tub • Sauna • Pond & Animals

Private 58-acre A-Frame retreat in the Kentucky Appalachians with mountain views, a stocked fishing pond, hot tub, infrared sauna, fire pit, games, and rare farm animals. Meet Suffolk Punch draft horses, a Highland cow and calf, and Thoroughbreds by request. No TV by design, just nature, stillness, connection, and a true farm-stay experience. Sleeps 7. Designed for families, couples and friends seeking nature, privacy and unforgettable memories.

Private 12 Acre Escape - Hot Tub, Firepit, Arcade

12 acres of peace and quiet in Campton. You can wander the trails, kick back by the firepit, or just take in the forest views. Evenings are for porch sunsets, hot tub stargazing, and the sound of birds all around. Inside, there’s a vintage Ms. Pac-Man for a little throwback fun. We’re about 15 miles from Red River Gorge, but it feels like you’ve got the whole place to yourself—no close neighbors, no traffic, just dark skies and starry nights.

Romantic Cabin • Private Hot Tub • Red River Gorge

“Absolutely loved this place! Everything was extremely clean, the hot tub was perfect, and the peaceful atmosphere made our stay unforgettable” — Luis ⭐️⭐️⭐️⭐️⭐️ Escape to The Outpost, a design-forward cabin tucked into six wooded acres in the foothills of Red River Gorge. Floor-to-ceiling windows frame the woods, while high ceilings and an open layout keep this cozy hideaway bright, calm, and connected to nature.