Holiday rentals in Jackson

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Top-rated holiday rentals in Jackson

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite

The room features two spacious beds with distinctive triangular headboards made of wood. A nightstand with a lamp is positioned beside one bed. The walls are decorated with forest-themed artwork, enhancing the cozy ambiance. A TV is mounted for added convenience.

Farm stay in Breathitt County

Farm Stay-Second Wind Cottage - Graham Estates LLC

Come get your second wind at our peaceful cottage designed for relaxation. Your family will love this quiet, serene home located up a scenic driveway. There is a large yard where you can feed the goats, enjoy the hot tub, or even end the day with a campfire. There is a walking trail around the property or you can drive approx. 35 minutes to Red River Gorge for an array of activities including kayaking, rock climbing, and hiking. So many memories are awaiting to be made at Second Wind Cottage.

4.99 out of 5 average rating, 231 reviews

Guest favourite

A welcoming cottage is nestled among lush greenery, featuring a rustic wooden façade and a covered porch. A stone pathway leads to the front door, flanked by vibrant flowers and plants enhancing the natural setting. Tall trees provide shade and enhance the tranquil atmosphere.

Farm stay in Jackson

Holler Hideaway

Need some peaceful time away? Search no more, as you have found “Holler Hideaway”, a secluded peace of heaven nestled in the head of hollow in Breathitt County. A two bedroom cottage style home is surrounded by scenic woods and field land. There are 47 acres of land for hunting, hiking,a small pond for light fishing, a barn to bring your own horses if you wish or just enjoy the peace and quiet. It’s 40 miles from hiking, kayaking, and rock climbing at Natural bridge. and the Red River Gorge

4.89 out of 5 average rating, 71 reviews

Top guest favourite

Cabin in Campton

Hill Haven | Cozy RRG Cabin + Hot Tub in the Woods

Welcome to Hill Haven! Escape to a secluded cabin getaway perfect for couples or small families seeking comfort, adventure, and relaxation. What our Guests Rave About: 🌲 Secluded yet central: Private forest setting just minutes from RRG trails, climbing, and local favorites 🛁🔥 Outdoor oasis: Hot tub, fire pit, string lights, and seating for relaxing evenings under the stars ✨ Spotless & cozy: Clean, comfortable interiors with thoughtful décor, modern amenities, and inviting atmosphere

4.99 out of 5 average rating, 163 reviews

Top guest favourite

A spacious deck overlooks a lush green valley with rolling hills blanketed in morning fog. A circular hot tub is positioned on the deck, providing a tranquil view of the mountains in the distance. The scene is illuminated by soft sunlight.

Guest house in Stanton

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

4.98 out of 5 average rating, 380 reviews

Top guest favourite

A charming farmhouse exterior features a black metal roof and white walls. Hanging ferns adorn the front porch, which is surrounded by well-maintained flower beds and greenery. A small outdoor seating area with red chairs complements the inviting façade.

Home in Campton

Emilys Welcome Inn B&B Minutes from Red Rvr Gorge.

Escape to a bygone era at our charming 1880's Vernacular Victorian-style farmhouse. Immerse yourself in history, surrounded by Lacy family heirlooms. Enjoy the perfect blend of nostalgia & modern convenience. We have good wifi & cell service. We welcome children but they will need supervision. Nov 1 - Jan 10 children are discouraged due to the Christmas decor. Sorry, we cannot accommodate pets. Experience the warmth & hospitality of our historic farmhouse B&B. Book your stay today.

4.96 out of 5 average rating, 89 reviews

Top guest favourite

A modern black house is set on a rocky landscape, surrounded by lush greenery. A wooden post carved with bear figures adds natural charm. Large windows invite light into the home, enhancing the connection between indoor and outdoor spaces.

Cabin in Wellington

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.

4.99 out of 5 average rating, 173 reviews

Guest favourite

The kitchen features modern stainless steel appliances, including a refrigerator, oven, and microwave. A wooden countertop with a sink is visible, along with cabinetry for storage. Natural light streams through a window above the sink, and a door leads outside.

Cabin in Beattyville

Cabin on the Grade Climbers welcome. Near RRG/BRRP

Newly refurbished cabin with a brand new addition! Enjoy the view of what used to be the Railroad during the 1930s but is now a gravel road surrounded by hills and fields. The cabin is located just minutes from the convenience of town but still isolated enough to enjoy the peace and quiet of the country. The cabin sleeps five, has a large front porch and a secluded back porch with an outdoor shower. It is an approximate 30 minute drive to Natural Bridge State Park, RRG and BRRP.

4.81 out of 5 average rating, 27 reviews

Top guest favourite

Cabin in Beattyville

The Crooked Cabin | Wood-Fired Hot Tub near RRG

Step into a fairytale at The Crooked Cabin, a one-of-a-kind woodland escape tucked away in the hills of Kentucky. Built with crooked windows, whimsical details, natural wood and imagination, this cozy hideaway feels like another world. Wander the forest, relax by a fire, soak under the stars in a wood-fired hot tub, and listen to the nearby spring. Discover the story of GhondlePop and Doris MossBottom, the mysterious woodland couple who helped bring The Crooked Cabin to life.

5.0 out of 5 average rating, 9 reviews

Top guest favourite

An inviting sleeping area features a cozy bed adorned with a nature-themed coverlet. Two windows framed by dark curtains allow natural light to fill the space. Wildlife photographs adorn the walls, contributing to the rustic charm, while a nightstand and lamp are positioned beside the bed.

Cabin in Campton

The Homestead at Hundred Acre Holler

Hundred Acre Holler is a beautiful stretch of land in the Appalachian Mountains near Campton, KY. With exceptional hiking, fishing, and hunting opportunities, incredible views, and just 15 miles from Red River Gorge State Park and the Kentucky Reptile Zoo, Hundred Acre Holler is the perfect place for a weekend getaway, or a home away from home. This listing is for Homestead, suitable for up to four guests. For other cabins, please see our listings.

4.96 out of 5 average rating, 137 reviews

Top guest favourite

Home in Irvine

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.

4.99 out of 5 average rating, 137 reviews

Top guest favourite

A rustic cabin features a welcoming wooden facade with multiple large windows. A covered front porch with yellow seating is visible, surrounded by lush greenery. The entrance is flanked by steps leading up from a gravel path, inviting guests into a serene natural setting.

Cabin in Campton

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.

4.97 out of 5 average rating, 229 reviews

Top guest favourite

A modern black cabin is surrounded by lush greenery, featuring a spacious deck that extends into the forest. A fire pit with seating is situated nearby, where a warm fire crackles, creating an inviting atmosphere for relaxation and gathering.

Cabin in Rogers

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.

4.98 out of 5 average rating, 219 reviews