Vacation rentals in North Middletown

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Top-rated vacation rentals in North Middletown

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Guest favorite

A private entrance is framed by trees displaying vibrant autumn foliage, adding bursts of red and orange. A gravel driveway leads toward a gated entrance, while fallen leaves create a colorful carpet along the pathway. Clear blue skies provide a bright backdrop.

Home in Lexington

4.95 out of 5 average rating, 361 reviews

Horse Farm Creekside Cabin- 6 min to KY Horse Park

*Fiberoptic wi-fi added 10/11/22*Gorgeous N. Elkhorn Creek views from every room in this 1200 ft cabin on a private, gated horse farm. Your only neighbors are friendly horses! Wi/fi, SatTV/Netflix or enjoy wildlife viewing on the screened porch. Big Green Egg for grilling on the spacious deck. Fire pit and zipline. Living room/bedroom dual wood burning fireplace for chilly nights. Fully stocked granite kitchen. Kayaks available. Minutes to the Legacy Trail. 15 min to downtown Lex/G’town.

Top guest favorite

A red farmhouse tractor is positioned prominently in the foreground, with a vibrant red caboose labeled 'SOUTHERN X525' in the background. An outdoor pavilion with a gabled roof is partially visible, bordered by trees displaying autumn foliage.

Train in Lawrenceburg

4.99 out of 5 average rating, 429 reviews

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of elm trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunk-beds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

Top guest favorite

A wooden sign displays the name 'Misfit Farm,' featuring a painted design of a red barn, a tree, and a cow against a rural backdrop. The sign is framed by natural wood and positioned near a fence lined with green grass.

Home in Paris

4.91 out of 5 average rating, 88 reviews

Misfit Farm

Need to get away? Misfit Farm sits 700’ from the road, offers 3 bedrooms, a spacious kitchen & dining area for family meals and a theatre room to enjoy. 2 bedrooms have queen beds and 1 has a twin daybed with a trundle underneath. After a long day you can enjoy the 10' x70' covered porch while watching the sunset. 6 guests can make this a home base for visiting local farms, horse events and bourbon trails. We are just 40 minutes from Lexington where you can enjoy Rupp Arena & Keeneland.

Top guest favorite

A rustic cabin is nestled among vibrant autumn trees, positioned above a serene pond. A small dock with two chairs is visible near the water's edge, inviting relaxation. The surrounding landscape features lush greenery and colorful foliage, enhancing the cabin's secluded feel.

Cabin in McKee

4.97 out of 5 average rating, 392 reviews

Mountain Dream Cabin -Fish Pond+Fenced Yard+Stalls

Escape to a peaceful cabin with a wraparound porch perfect for soaking in the beauty of nature. This pet-friendly retreat features a fenced yard and space for trailer parking, plus four horse stalls available upon request. Enjoy catch-and-release fishing in the stocked pond, or explore nearby attractions: 25 minutes to Berea’s historic downtown and Pinnacle Trails, and 30 minutes to Flat Lick Falls and Sheltowee Trace. Unwind, explore, and experience the charm of our small-town getaway!

Guest favorite

A traditional bedroom showcases a four-poster bed with a patterned comforter. A decorative lamp sits on a bedside table, and a vintage console table with a plant adds a touch of greenery. Natural light enters the room through the open door, enhancing the serene ambiance.

Guesthouse in Winchester

4.93 out of 5 average rating, 204 reviews

Carriage House on the Park

Enjoy the tranquility of this Upstairs Apartment (over 400 sq ft) suite, located across from Winchester's College Park. Executive amenities include heated bathroom floor tile, additional sink and vanity and large flat screen Roku Smart TV. Carriage house is located just steps from public gym and recreational center and historic downtown Winchester. Centrally located with easy access to Lexington, Paris, Versailles, Georgetown, Kentucky Horse Park, Natural Bridge and Red River Gorge.

Top guest favorite

The kitchen features a large central island with a dark finish, complemented by light granite countertops. Bright, white cabinetry surrounds the space, enhanced by overhead pendant lighting. Stainless steel appliances, including a refrigerator and microwave, provide modern convenience amid an open layout.

Home in Mount Sterling

5 out of 5 average rating, 83 reviews

High Street Hideaway home atmosphere for relaxing

High Street Hideaway, relax away from the city in a spacious well appointed home atmosphere. Large back deck for relaxing and dining. No need to park on the street and walk a flight of stairs! Private parking with 4-5 steps up to deck and back door! *Access to Lexington 30-45 minutes away via Interstate 64. * 45 minute drive to the natural beauty of Red River Gorge for hiking/ climbing *30 min to Cave Run Lake * Three blocks to local shops, eateries, and town festivals!

Top guest favorite

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

4.91 out of 5 average rating, 831 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.

Top guest favorite

A white, two-story house is framed by lush greenery and brick pathways. An inviting front porch is adorned with a decorative railing. A garden with a fountain and flowering plants enhances the exterior, creating a charming and welcoming entrance.

Farm stay in Paris

4.94 out of 5 average rating, 16 reviews

Carriage House

Unwind with the spacious area this apartment has to offer. It is located on a working horse farm above the shop, in the renowned Bluegrass region of Ky. At Houstondale you can stroll to the barn and visit the horses or hide away in your space and relax. The KY Horse Park is a 22 minute drive, Lexington is 25 minutes and you are 30 minutes from horse racing at Keeneland Race Track. Even with the remote feel you are only 1 mile from Walmart, shops, and downtown Paris.

Top guest favorite

The exterior of a rustic barn is surrounded by green lawn and mature trees. A balcony is visible above the entrance, framed by wooden beams. The barn's facade features a blend of light wood and contrasting dark accents, contributing to its farm charm.

Barn in Paris

4.96 out of 5 average rating, 91 reviews

Horse & Flower Farm Barn Loft

Enjoy peace and quiet in the countryside surrounded by Stoner Creek. Old Bridge Farm is a horse farm and also the home of Blooms of Bourbon County which is a flower, fruit and vegetable grower utilizing organic growing practices. Our 100 year old tobacco barn has been converted into a stable with a large rustic loft above with all of the conveniences of home. We're off the beaten path on a very quiet road in the middle of horse country. Come...relax, escape, recharge.

Superhost

Farm stay in Winchester

4.81 out of 5 average rating, 129 reviews

The Winchester Retreat

Welcome to the Winchester Retreat! We are located right off of I-64 in Winchester, just 30 minutes from both Lexington and the Red River Gorge. We're right down the street from Winchester's downtown, boasting restaurants, breweries, and shops. Pet friendly!! Come spend an evening by the fire pit and whip up a great dinner using our fully equipped kitchen or charcoal grill. We're also close to Legacy Grove Park, complete with a walking trail and dog park.

Guest favorite

The living area features rustic log walls contrasted by a bright ceiling. A cozy sectional sofa faces a wooden coffee table and a small desk with a TV. Two armchairs are positioned beside a colorful area rug, while natural light filters through multiple windows.

Cabin in Lexington

4.82 out of 5 average rating, 591 reviews

Unique Stay - 1907 Log Cabin Near Kentucky River

Kirkland Cabin - Stay in a 1907 Log Cabin Perched on the Palisades of The Kentucky River in Lexington. * 2022 Updated Kitchen * King Bedroom and fun loft offering 2 single beds (ladder access) & 1 full bath. This is a cabin built in 1907 & has the character to prove it. Unplug with games or utilize High-speed WiFi. This cabin is 1 mile from I-75 & 15 minutes to downtown Lexington. Enjoy dinner < 1 mile away at Proud Marys BBQ w/ Live music (seasonal)

Guest favorite

A welcoming living space features hardwood flooring and soft gray walls. A comfortable sofa and patterned armchairs are arranged around a rustic coffee table. Ceiling fans provide ventilation, while large glass doors open to a view of the expansive yard.

Farm stay in Carlisle

4.99 out of 5 average rating, 160 reviews

Hilltop Retreat at Wendt’s Wildlife Adventure

Take it easy at this unique and tranquil getaway. Newly remodeled home on a 125 acre farm that is home to Kentucky’s newest wildlife park & Daniel Boone’s last home in Kentucky. Expansive views, and a visit to Wendt’s Wildlife Adventure (open seasonally), which is owned & operated by your hosts, are sure to give you just the right amount of rest & adventure that you are seeking.