Vacation rentals in North Middletown

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Top-rated vacation rentals in North Middletown

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Top guest favorite

A small pony is depicted grazing in a grassy area, surrounded by two cats resting nearby. The fenced pasture in the background enhances the rural setting, with green panels visible behind the animals.

Farm stay in Winchester

4.92 out of 5 average rating, 152 reviews

LenMar Farm Country Stay near Lexington KY

Farm stay in the heart of the Kentucky Bluegrass 20 min from the Kentucky Horse Park and downtown Lexington. 30 min to Keeneland. 45 min to Red River Gorge. Quiet, private walk out basement apt. with 2 bedrooms, great room, and butlers pantry with coffeemaker, small refrigerator, microwave, and kitchen basics. Space is not shared. Eat indoors or out, fire pit and horses/cattle out back. Up to 2 well-behaved dogs with pre-approval from hosts. Dogs can’t be left alone. 2 night min, 10 night max.

Guest favorite

The calm surface of N. Elkhorn Creek reflects the vibrant greenery of surrounding trees. Soft ripples traverse the water, created by a kayak's bow, while sunlight dances on the surface, enhancing the natural serenity of the area.

Home in Lexington

4.95 out of 5 average rating, 356 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 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, 85 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

Cabin in McKee

4.97 out of 5 average rating, 367 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 charming exterior view of the house features a welcoming porch with decorative plants and an American flag. A concrete pathway leads from the sidewalk to the entrance, flanked by manicured lawn areas and mature trees providing shade.

Guesthouse in Winchester

4.94 out of 5 average rating, 201 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.

Guest favorite

An open space features a large glass garage door adorned with a view of greenery, allowing natural light to fill the area. Two metal stools are positioned at a small wooden bar against the wall, providing a cozy spot for relaxation or meals.

Treehouse in Georgetown

4.93 out of 5 average rating, 222 reviews

Treehouse with TWO outdoor tubs by the creek!

Welcome to your romantic treehouse getaway! Nestled among the trees, this one-bedroom treehouse is the perfect spot if you're looking for a unique & unforgettable experience. The treehouse features a large glass rolling garage door allowing stunning views of the sunset, but the highlight is undoubtedly the double tubs overlooking the creek. ✔ Queen Bed ✔ Outdoor Deck with Seating ✔ Double Outdoor Bathtubs ✔ Outdoor Shower ✔ Composting Toilet ✔ Creek Access ✔ Indoor Cooking Station

Top guest favorite

Home in Mount Sterling

5 out of 5 average rating, 74 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

A small outdoor seating area features two bright red chairs and a round table on a pebbled surface. A lush green lawn extends into the distance, framed by trees and a wooden fence, creating a peaceful outdoor retreat.

Home in Winchester

4.91 out of 5 average rating, 813 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

Two horses are seen in a green paddock, with a wooden fence in the foreground. Vibrant pink and purple flowers are blooming nearby, adding color to the natural landscape. Lush trees in the background provide a serene atmosphere.

Barn in Paris

4.95 out of 5 average rating, 88 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.

Top guest favorite

A neatly arranged stack of textured dishware is visible on a shelf, featuring various sizes of bowls and plates in a soft beige color. A transparent glass tumbler stands alongside, adding a touch of contrast to the arrangement.

Guest suite in Lexington

4.99 out of 5 average rating, 197 reviews

The Gainesway Suite-Near UK/Hospitals/Keeneland

A posh Guest Suite in popular Gainesway! Centrally located in a friendly, established neighborhood. Minutes to Lexington's best Concert Venues, Restaurants, UK, Rupp, Hospitals, and Shopping! Private entrance, luxurious and stylish furnishings, plus your own laundry room! Perfect for a night in town, traveling for a ballgame or show, visiting our famous distilleries and Keeneland! The suite is also equipped for longer stays, business travelers, you name it!

Superhost

A clean bathroom space includes a toilet and a storage shelf with magazines. A cozy couch is visible in the adjacent area, contributing to a relaxed atmosphere. Natural light enters through a nearby window, enhancing the overall brightness of the room.

Farm stay in Winchester

4.82 out of 5 average rating, 114 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

A replica of the Eiffel Tower is prominently displayed in a vibrant public square, surrounded by colorful flowers. The structure is positioned against a backdrop of a historic brick building, with signage indicating 'Paris, Kentucky' at the base, inviting visitors to explore the unique locale.

Condo in Paris

4.94 out of 5 average rating, 114 reviews

Paradise Inn B&B - Lover's Suite

The only B&B in Kentucky with an ‘Eiffel Tower’ view! Paradise Inn B&B is a unique penthouse suite atop "The World's Tallest Three Story Building" (from Ripley's Believe It or Not!) with exquisite oriental decor from the far East. The unbeatable hospitality is provided by your host and the owner, Lee Nguyen. This stay includes a $25 gift certificate for Paradise Cafe - Asian fusion and Pho restaurant located on the first floor.

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Popular amenities for North Middletown vacation rentals

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Free parking on premises

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Other great vacation rentals in North Middletown

Guest favorite

A modern electronic keypad door lock is shown mounted on a door. The sleek design features illuminated numbers for easy visibility, ensuring secure entry. A keyhole is positioned beneath the keypad, contributing to the lock's functionality.

Home in Millersburg

5 out of 5 average rating, 22 reviews

The Booth House

MelissaRating, 5 stars1 month ago

I grew up in this small town and I had to come back for a graduation. The house was so comfortable. I never even left Millersburg. Usually, I’ll go in visit Lexington, but we stayed in the house played Uno, watch TV and made family dinners. The towels are soft, the house is homie and everybody was so kind.

Guest favorite

An aerial view captures the Tisbury House farmhouse surrounded by lush green fields. A pond is visible nearby, and a winding road leads to the property. The farmhouse features a brown roof and well-maintained landscaping, embodying the serene countryside atmosphere of Kentucky horse country.

Home in Paris

5 out of 5 average rating, 6 reviews

The Tisbury House

RobinRating, 5 stars1 month ago

One of the nicest, most comfortable places we have stayed with Airbnb. I think the cleanest place ever as well, which is always important to me. Highly recommend!!

Top guest favorite

A view of the county courthouse features its prominent clock tower and white façade, under a clear blue sky. Nearby buildings showcase a blend of historical and modern architecture. Vehicles are seen parked along the street, highlighting the bustling downtown atmosphere.

Apartment in Winchester

4.94 out of 5 average rating, 96 reviews

The Carriage Inn - 1-bdrm apt in historic downtown

ChristopherRating, 5 stars2 weeks ago

This was the perfect place for a weekend stay with my little one. I would definitely stay here again

Superhost

A world-class kitchen features an open layout with modern cabinetry and a large island with bar seating. Natural light fills the space through several windows, highlighting the wood beams on the ceiling. Luxury appliances are visible, enhancing the kitchen's functionality.

Home in Paris

4.78 out of 5 average rating, 9 reviews

Charming historic home

JennyRating, 5 stars2 months ago

Beautiful historic home. Great location to downtown and several cute coffee shops within walkable distance. We would definitely stay there again if ever in the area.

Guest favorite

Farm stay in Winchester

4.9 out of 5 average rating, 68 reviews

Renovated historic home on working cattle farm

ShannonRating, 5 stars3 days ago

Absolutely amazing! Peaceful surrounding! Amazing sunsets! Host provided more than just bare minimum supplies that you may have encountered in other air bnbs. If you are looking for a peaceful getaway that is just in reach of shops and restaurants but outside of the hustle and bustle this is it!!

Guest favorite

Home in Mount Sterling

4.88 out of 5 average rating, 205 reviews

THE DOLLY - Cozy, Bright Home in Historic Downtown

RobertRating, 5 stars1 month ago

We've stayed at The Dolly before, and it's one of our favorite places! Lot's of space, very comfortable bed, and extra clean. Highly recommend!

Top guest favorite

An outdoor seating area is presented with two wooden chairs and a matching table, surrounded by greenery and a brick patio. A grill is positioned nearby, and an ornate gate leads to a scenic view beyond the property.

Home in Georgetown

4.99 out of 5 average rating, 91 reviews

Quaint cottage on scenic horse farm

JuliaRating, 5 stars1 week ago

This well decorated, clean, peaceful home was a highlight of our stay. My son had room to throw the baseball, my youngest caught fireflies, my oldest spent time petting the 7 foals, and I read in a chair under a huge tree. Georgetown was a great location for us as well. Beds were clean and comfortable, towels were soft and fluffy. I highly recommend.

Top guest favorite