Vacation rentals in North Middletown

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Top-rated vacation rentals in North Middletown

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Top guest favorite

A wooden sign reading 'LENMAR FARM Est. 2019' is prominently displayed on a green metal gate. The sign showcases a natural wood grain, and the background features an open field with scattered trees and horse jumps.

Farm stay in Winchester

4.92 out of 5 average rating, 158 reviews

LenMar Farm Country Stay near Lexington KY

Farm stay in the heart of the Kentucky Bluegrass 20 min from the KY Horse Park and downtown Lexington. 30min to Keeneland. 45min to Red River Gorge. Quiet, private walk out basement apt. with 2 bedrooms, great room, fooseball and butlers pantry w/ 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.

Top guest favorite

A rustic wooden box labeled 'Farmhouse' holds jars filled with daisies and assorted natural elements, set against a green field. A cow stands nearby, framed by soft evening light, with trees in the background, creating a peaceful farm scene.

Farm stay in Winchester

4.97 out of 5 average rating, 122 reviews

Family Farm Winchester/Lexington 20 min.*Game Room

Franklin Ridge Farm is 5 minutes to DT Winchester close to Lexington 5min. access to I64; 15min. to I75 Savings:Aug. Centrally located: Eateries & Historical Sites Lexington 20min State Parks Meadow Green Music Park 20min Keeneland 30.4mi. Kentucky Horse Park 30min Red River Gorge 35min Ark Encounter 45min Creation Museum 1hr 30min ~Home is surrounded by our family farm EST 1803 at the beginning of Scenic Rt.15 *All guests must be registered to see the total price of your stay before booking

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, 360 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, 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.

Superhost

A cozy bedroom features blue walls adorned with butterfly decor and soft lighting. A queen bed is dressed with a floral comforter and surrounded by an inviting area rug. A small couch and side table add to the room's charm, with doors leading to additional living spaces.

Home in Mount Sterling

4.85 out of 5 average rating, 212 reviews

THE DOLLY - Cozy, Bright Home in Historic Downtown

Hello, Dolly! This bright and cozy home in the heart of downtown Mt. Sterling provides comfort and convenience. With hundreds of unique artifacts and rare photos to discover, you will find peace, relaxation, and tons of Dolly-themed photo ops! In addition to WiFi and Roku TV, guests will enjoy a massive collection of Dolly Parton films, records, and books. A fully-themed kitchen, bedroom, dining room, and bathroom offer many fun Dolly touches. A place so cute, even Jolene wants to stay!

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 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, 829 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

4.8 out of 5 average rating, 126 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, 587 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.