Vacation rentals in North Middletown

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in North Middletown

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

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

4.93 out of 5 average rating, 165 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.

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

4.96 out of 5 average rating, 368 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 spacious living area features a comfortable sectional sofa accompanied by a recliner. A patterned area rug covers the floor, and a coffee table stands nearby. A fireplace is set against a white brick wall, with decorative shelves holding various items above.

Home in Richmond

4.96 out of 5 average rating, 141 reviews

Near to EKU; discounts to 10%

Located 5 minutes from I-75. Newly renovated basement apartment perfect for solo travelers, friends or couples and is pet friendly. Take it easy at this country setting and enjoy the pool. Convenient to EKU, stay after a day at Keeneland, exploring the Bourbon Trial, concerts or just a peaceful and relaxing getaway. Available small hot tub on request. Guest space has own entrance and is separate and independent from host’s space. 5-10 minutes restaurants, groceries, gas, drug stores and banks.

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

4.83 out of 5 average rating, 216 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, 208 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, 851 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 favorite

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, 159 reviews

The River House Floor 2 Getaway, w/a river 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.

Top guest favorite

A serene bedroom features a spacious bed dressed in a navy blue coverlet and decorative pillows. Natural light filters through two large windows adorned with blinds, illuminating the warm wood flooring. A small decorative bench sits beside the bed, complemented by a nightstand and a framed piece of art on the wall.

Apartment in Winchester

4.94 out of 5 average rating, 106 reviews

The Carriage Inn - 1-bdrm apt in historic downtown

Centrally located in historic downtown Winchester with views of the county courthouse. Apartment is upstairs in a building that was originally used as a carriage repair shop. It is within walking distance to lots of unique shops and restaurants and the Bluegrass Heritage Museum. Walk or drive to the Farmers Market (seasonal) on historic Depot Street on Saturday mornings. The Red River Gorge/Natural Bridge area is 40 minutes east. Lexington is a short 20-30 minutes west.

Superhost

Farm stay in Winchester

4.81 out of 5 average rating, 137 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

4.83 out of 5 average rating, 602 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

The exterior of a historic three-story building is presented in warm yellow and brown tones. Large windows with white drapes adorn the upper floors. A colorful sign for Paradise Cafe is visible at street level, complemented by a few potted plants lining the entrance.

Condo in Paris

4.94 out of 5 average rating, 119 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.

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, 162 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.