Holiday rentals in Fleming County

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Top-rated holiday rentals in Fleming County

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Superhost
The exterior of a modern tiny home is showcased, featuring a spacious wooden deck with railings. A large grassy area surrounds the home, complemented by a clear blue sky. A dog relaxes in the foreground, contributing to the tranquil environment.
Tiny home in Flemingsburg
4.92 out of 5 average rating, 176 reviews

The Concord - Enjoy the Vineyard Views

Experience tiny home living without giving up the comforts of home. Kick back and relax in this modern 'spacious' tiny home loaded with the most up to date amenities - and Vineyard views right out your front door! This one bedroom home offers additional space for the family and kids with an upstairs loft and a roomy living area. Added bonus - you're a short walk to our family owned winery and restaurant! Plus- many historic attractions just a short drive away. Come enjoy the luxury tiny life.

Top guest favourite
A quaint cottage is set against a backdrop of lush greenery and rolling hills. The structure features a porch with rocking chairs, and large windows provide natural light. Towering trees surround the property, contributing to the serene atmosphere.
Farm stay in Morehead
5 out of 5 average rating, 29 reviews

Morehead Farm Cottage

This memorable place is anything but ordinary. Nestled at the front of our family farm, enjoy a cup of coffee on the front porch, or catch the best sunsets in Kentucky. This one bedroom cottage includes a sleeping loft, full bath with laundry, and a full sized kitchen. Stretch your legs exploring the vineyard or fishing the ponds next to the cottage. We are a working farm with chickens, gardens, and the farm dogs. We are just 4 miles from I-64 and 8 miles from Morehead State University Campus.

Top guest favourite
A charming two-story country home is set on a gently sloping lawn, featuring a red front door and several windows that allow natural light. Green shrubs and grass surround the entrance, complemented by a clear blue sky overhead.
Home in Sharpsburg
5 out of 5 average rating, 18 reviews

Firethorn’s Hilltop Haven

Country living at its finest. The home is nestled on a 140 acre seasonal working farm with lush open fields in scenic rural but Central Kentucky. This peaceful getaway gives a glimpse of what life on the farm and being in nature is like. Surrounded by open rolling fields, the perfect place to relax, take a walk, take a dip in the pool, or just be in nature. This home has it all. Family friendly. Pool available from May 19th to September 9th. Rates apply. Can park RV's & trailers.

Superhost
A calm lake is depicted, surrounded by lush greenery and gentle hills in the background. The water reflects the cloudy sky, creating a serene environment. Tall grass borders the lake's edge, enhancing the natural landscape.
Home in Wallingford
4.69 out of 5 average rating, 16 reviews

Bourbon Flights Country Cottage

Escape to the heart of nature at our secluded cabin located on a sprawling 433 acre farm, nestled a mile off the main road for the ultimate privacy with hunting option’s, ask for rates. Our cozy country cottage offers all the amenities to make you feel right at home, including enough space for up to 8 guests. This outdoorsman's paradise offers an 18 acre lake for swimming, fishing or simply just enjoying the view. It’s not a family trip without pets, bring the dogs and horses too!

Top guest favourite
The cottage's exterior is characterized by a welcoming porch featuring rocking chairs and a bench. Black star accents adorn the light-colored siding, framed by green grass and trees. Large windows invite natural light, enhancing the view of the surrounding fields.
Home in Morehead
5 out of 5 average rating, 107 reviews

Sunset Cottage

Sunset Cottage is located among the farms and fields of Morehead, KY. Conveniently situated off of I-64, within 10 min. of Cave Run Lake, App Harvest, Ind. Stave Co., and MSU. This newly remodeled 2-bedroom home has 1 queen, 1 full, & 1 twin bed. A quaint living room with an elec. fireplace, full kitchen, dining area, washer/dryer & an outdoor space that includes a gas grill and fire pit. There is plenty of room to park your boat and a porch to relax and enjoy the beautiful sunset

Top guest favourite
A large converted barn with a striking red exterior is set against a vibrant sunset sky. The building features multiple windows and a spacious porch, while a grassy yard surrounds the property. Telephone poles and fencing are visible, enhancing the rural landscape.
Home in Hillsboro
4.94 out of 5 average rating, 66 reviews

HUGE Country Get Away-RELAX!

Huge converted barn! Unique rustic stay, the house barn is as big as two houses in one! It has two separate living areas, two kitchens, and multiple bedrooms! There is also a very large front yard, a concrete drive with ample parking, and a nice front porch to sit on. The listing is co-managed by me and my parents. This is my parents' (2 people) main home, so it is normally lived in, but way too large not to share with others! You will have the entire space when rented!

Top guest favourite
The farmhouse exterior features a light-colored facade with white shutters and a welcoming front porch. A curved pathway leads to the entrance, surrounded by a well-maintained lawn and neatly trimmed bushes. Two chairs are positioned on the porch, inviting relaxation.
Farm stay in Ewing
4.99 out of 5 average rating, 174 reviews

Haymark Farmhouse: cozy, country memories

Welcome to Haymark Farmhouse, built in 1907. Relax in front of the fireplace with electric logs, play games (provided), and cook in the well-supplied kitchen or on the gas grill out back. Enjoy the outdoor fire pit (wood provided) and the lighted sitting area and table for eight. Explore our 275 acre farm! Check out our cute farm animals, take a hike along the creek, catch a fish in the pond, hunt (message us for rates), watch a sunset ...Enjoy your time at Haymark Farm.

Guest favourite
A fully equipped kitchen features modern appliances, including a stove, refrigerator, and microwave. White cabinetry and checkered patterns create a clean aesthetic. Countertops are organized, with cooking utensils readily available. A small rug lies near the sink, adding a touch of comfort to the space.
Guest suite in Flemingsburg
5 out of 5 average rating, 5 reviews

Autumn Blaze Comfort

WE ACCEPT ONE NIGHT STAYS!! This suite is located out in the country on our 45 acre farm. Everything is new and cozy and comfortable to be your home away from home.There is ample free parking just outside the door. We invite you to come and enjoy the beautiful Sugar Loaf Mountain view. During the summer you will love the chirping of the purple martins who come to nest every summer in the gourd martin house we've provided for them.

Top guest favourite
Home in Flemingsburg
5 out of 5 average rating, 25 reviews

Red Bird Estates

Escape to our cozy, remodeled farmhouse—perfect for couples, families, or friends. Decorated just in time for Christmas. Enjoy 3 comfy bedrooms, a clean bathroom, a fully stocked kitchen, and a game-friendly living room. Relax on the back deck with peaceful views, unwind by the firepit, or swing on the tree swing or relax in the hammock. Whether you're here to rest or explore, this charming country home is the perfect getaway.

Guest favourite
The exterior of Shady Pines Inn is visible, featuring a one-story brick structure surrounded by lush greenery. Sunlight filters through the leaves of trees, highlighting the manicured lawn and a wooden storage unit positioned near the side of the house.
Home in Morehead
4.92 out of 5 average rating, 203 reviews

Shady Pines Sheltowee MSU Cave Run

Shady Pines Inn is a vacation rental located .7 mile from Exit 133 off interstate 64. Ten minutes to Cave Run Lake and Morehead. 3 bedrooms, king, queen & 2 twin beds, 2 new cots with memory foam toppers. 1.5 baths,living room with 2 couches & 3 chairs. Full kitchen, accessible tub/shower. Snacks, cereal/granola bars, oatmeal, donuts, bread, bagels, local eggs, coffee, tea. Any combination of these items will be offered.

Top guest favourite
The exterior of a historic distillery building from the 1860s is shown, featuring exposed brick walls and a neatly maintained façade. Two stories of windows are framed by wooden accents, and an inviting entrance is flanked by stone pillars, contributing to the building's historical charm.
Home in Flemingsburg
5 out of 5 average rating, 26 reviews

1860's building brought to life

This 1860's original distillery building will take you back in time with it's spacious yet cozy areas to relax and enjoy. Exposed brick exterior walls surround you while belt driven fans keep you cool as you relax and read a good book, play some games with the kids or enjoy a nice dinner at one of the many seating areas. We hope you enjoy your stay in our home as much as we enjoyed living here!

Guest favourite
A welcoming porch features a pink front door, surrounded by two green chairs and a small circular table. The wooden deck is covered, providing shade, while nature is visible in the background, contributing to a sense of tranquility.
Tiny home in Ewing
5 out of 5 average rating, 41 reviews

The Cottage at Stillhouse Cabin

Peaceful private Cottage on the edge of a forest with walking trails thru out the 46 acres. A swing in front yard to watch sun rise over the Hills of Kentucky. This 2 bedroom Cottage is a perfect getaway to unwind and relax. Close to State Parks, Historical sites in Northern Kentucky and the local Breweries. After a day of site seeing turn the grill on, start the firepit and enjoy the sunset.

Popular amenities for Fleming County holiday rentals