Holiday houses in Boonesborough

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Top-rated holiday rentals in Boonesborough

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Guest favourite

A close-up view captures the bubbling surface of a hot jacuzzi, steam rising gently into the air under a bright sun. The light reflects off the water, creating a serene atmosphere, while trees in the background provide a natural setting.

Home in Lexington

4.91 out of 5 average rating, 225 reviews

Cottage w/Jacuzzi - centrally located, comfy beds!

Keep it simple at this peaceful & centrally-located house with hot, clean jacuzzi year-round (jets are old!). Comfy beds, cozy linens & a good sleep are the hallmark of our BnB. The focus is family, friends & interacting through good ol’ conversation. Plenty of room in kitchen for good meals! Lots of books in the library for a good read & art from local artists - all for sale. Close to downtown, campus, NOLI District, New Circle, I-75/I-64. Great stay for traveling professionals, nurses/doctors.

Top Guest favourite

A scenic view of a poolside deck captures the early morning sun rising over the mountains. A pair of Adirondack chairs are positioned nearby, beside a firepit. The serene landscape is featured with rolling hills and a layer of mist hovering in the valley.

Guesthouse in Stanton

4.98 out of 5 average rating, 347 reviews

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

Guest favourite

A newly constructed A-Frame cabin is set against a backdrop of bare trees and a clear blue sky. Steps lead up to a spacious deck, emphasizing the cabin's inviting entrance. The exterior features a combination of neutral tones and crisp lines, reflecting modern design.

Cabin in Stanton

4.96 out of 5 average rating, 122 reviews

New! Mountain Top A-Frame Cabin, The Triangles

Escape to your mountain top sanctuary where breathtaking views leave you in awe . This newly constructed A-Frame cabin invites you to immerse yourself in the tranquility of nature while indulging in modern comforts. Relax in the hot tub while enjoying stunning sunsets and gorgeous nature views all around. With meticulous attention to detail, each corner of this retreat exudes a personal touch, ensuring a truly unforgettable getaway amidst the wilderness. 20 mins to RRG! The Triangles

Top Guest favourite

A charming cottage exterior is framed by lush greenery and mature trees. The light gray siding is complemented by white columns at the entrance. A brick walkway leads to the front door, bordered by neatly manicured bushes and seasonal flowers.

Home in Georgetown

4.98 out of 5 average rating, 122 reviews

Quaint cottage on scenic horse farm

Welcome to the Cottages at Oxford Springs Farm. Enjoy a quiet stay in the largest cottage of our 3 newly remodeled rental properties, all located on this beautiful, small working thoroughbred farm. Views from every window capture the beauty of the bluegrass. Conveniently located only 10 miles from the Ky Horse Park, 5 mi from the quaint historic town of Georgetown, and 30 minutes from some of Kentucky’s greatest bourbon distilleries. For wildcat fans, Rupp Arena is only 15 minutes away.

Top Guest favourite

A custom California King wooden bed is featured within an immersive room, surrounded by dark hues and dramatic lighting. Adjacent is a unique chair and a traditional rug, enhancing the room's historical charm and fantasy theme.

Apartment in Lexington

4.98 out of 5 average rating, 538 reviews

Game of Thrones - Downtown

Be the lord or lady of this palatial chamber, in the center of downtown‘s hottest spots. Your OMG stay comes w/royal features inspired by your favorite fantasy series. •Custom Calif. King wooden bed w/playroom features and a mini-dungeon (not just for containing dragons!) •Luxurious bathroom w/steam shower for two •Decor from Old World Europe: hand-crafted torch sconces, medieval-style weaponry and an iron throne •Custom Coffee Bar w/touch-screen access to your favorite cafe coffees

Guest favourite

A spacious glamping tent is set among vibrant greenery, featuring a conical roof and large entrance. Natural light filters through the trees, casting soft shadows on the wooden deck. The scene captures a peaceful ambiance, inviting guests to relax in nature.

Treehouse in Georgetown

4.94 out of 5 average rating, 305 reviews

★Escape & Relax ~ Breathtaking Creekside Getaway★

Escape the everyday hustle and bustle by immersing in the stunning glamping experience on a secluded creekside property. Enjoy solitude, romance or family time inspired by nature. Tucked away on our 13 acre residence, this spacious 16' tent offers a unique stay in a breathtaking ambiance. ✔ Queen Bed + 2 Full-Size Mattresses ✔ Outdoor Deck with Seating ✔ Bathtub + Separate Shower ✔ Composting Toilet ✔ Creek Access + Kayaks ✔ Cooking Station Learn more about this glamping haven below!

Guest favourite

The historic log home showcases a warm wood exterior, surrounded by lush green grass and colorful flower beds. Tall pine trees provide a serene backdrop, and a wide driveway leads to the entrance, highlighting the inviting and rustic charm of the property.

Farm stay in Richmond

4.95 out of 5 average rating, 228 reviews

Martin Manor: Authentic, historic log cabin

Surround yourself with beauty, art, and treasures of days-gone-by in this lovingly restored historic log home. Clear ponds, majestic pines, picnic tables and horses on the property. Near by attractions: Historic craft center Berea, Red River Gorge, horse racing at Keenland, and Kentucky Proud dining and activities in Lexington. Hot tub, washer/dryer, 2 fireplaces, 2 TVs, WiFi, porch swings, hammocks, grill, fire pit, paddle boats, dishwasher, filtered water, trash compactor and more.

Top Guest favourite

A modern kitchen is displayed, featuring sleek white cabinetry and stainless steel appliances. An island with seating is positioned at the center. Decorative plants and succulents are arranged on the dining table, complementing the contemporary decor.

Home in Richmond

5 out of 5 average rating, 112 reviews

Westwood

Stay in this newly renovated, freshly furnished 3 spacious bedroom 3.5 bathroom home in the heart of Richmond, KY. This home has many luxury features like a sunroom, granite countertops, and is walking distance to Eastern Kentucky University’s Campus. Included is a Smart TV in the living room, TVs in 2/3 bedrooms, adjustable AC/Heat, Serta Mattresses, and luxury furniture perfect for relaxing. We appreciate you staying with us, and feel free to reach out at any time during your stay!

Top Guest favourite

The entrance of the cottage features a wooden door framed by two windows, offering natural light. A decorative wreath adorns the door, and wall sconces provide additional illumination. The exterior showcases white siding with teal accents, complemented by a brick pathway leading to the door.

Home in Winchester

4.92 out of 5 average rating, 915 reviews

Cozy Cottage

Sweet little cottage within walking distance of historic downtown Winchester. Open floor plan, 500 square feet of coziness! Queen size bed, kitchen, living room, dining all in one place. We’re a working farm on the edge of the city limits in an older non-gentrified neighborhood. Surrounded by the Kentucky Horse Park, Keeneland, Rupp Arena, Fort Boonesboro, Red River Gorge and the Kentucky Bourbon Trail. Easy access to I-64, I-75, and Mountain Parkway - gateway to Appalachia.

Guest favourite

A wooden railing overlooks a serene river, with trees lining the opposite bank. A cozy plaid blanket drapes over the railing, alongside a glass decanter and two glasses, capturing the golden hues of a sunset.

Apartment in Winchester

4.89 out of 5 average rating, 177 reviews

Riverview 2 … enjoy the view !

Enjoy the spectacular views of the Kentucky River from this second-floor studio. Located within an easy walk of hiking trails and dining. Visit the Waterfront Grill or Hall’s on the River. A tasting at the winery just a few minutes away will sweeten your stay. For more play, kayak rental is nearby. This property is nestled on the riverbank. You will encounter bugs if you are enjoying the outdoors. We have regular exterminations, but an occasional cob web is to be expected.

Guest favourite

The kitchen features granite countertops and a modern layout, equipped with a black refrigerator, stove, and microwave. Light-colored cabinetry is complemented by white tiled backsplash. A round dining area offers high stools, and natural light filters through the window with horizontal blinds.

Apartment in Richmond

4.95 out of 5 average rating, 107 reviews

The Nelson House-Walk to EKU

This fantastic 2 bedroom apartment is located less than a minute walk to Eastern Kentucky University. This completely renovated apartment puts you within walking distance to campus as well as downtown. Granite countertop kitchen, complimentary coffee and snacks, and beautifully tiled bathroom. The bedrooms are located upstairs. We look forward to hosting you soon. Given that it is located downtown we provide noise machines and complementary earplugs for any street noise.

Superhost

An aerial view of Skyview Cabin showcases its unique construction elevated on stilts above a wooded landscape. The roof slopes downward, and a spacious deck extends toward the tree line. Surrounding trees display a seasonal mix of bare branches and greenery.

Cabin in Stanton

4.85 out of 5 average rating, 126 reviews

Suspended SkyView Cabin Near RRG

Welcome to Skyview Cabin! A unique all wood construction suspended over a cliffside. What sets our cabin apart is its unique perch – suspended 30 feet up in the air, offering a truly elevated experience. The property is peacefully secluded, yet just a short 20 minute drive to Red River Gorge. Enjoy a nice soak in the hot tub after taking part in all the RRG has to offer : swimming, kayaking, boating, biking, fishing, golfing, hiking, caving, and rock climbing.