Holiday houses in North Middletown

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Top-rated holiday rentals in North Middletown

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Guest favourite

Farm stay in Winchester

4.94 out of 5 average rating, 108 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.

25 June – 2 July

$1,059 AUD total

Guest favourite

Home in Paris

4.82 out of 5 average rating, 39 reviews

Misfit Farm

Need to get away? Misfit Farm sits 700’ from the road and offers a newly renovated 3 bedroom Airbnb with a 10’ x 70’ covered porch & a fire pit. There is a spacious kitchen & dining area for family meals and a theatre room to enjoy a movie. Two bedrooms have queen beds and one a twin daybed with a trundle underneath. 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.

23 – 30 Sept

$1,536 AUD total

Guest favourite

Home in Mount Sterling

4.93 out of 5 average rating, 145 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!

21 – 28 Jan

$958 AUD total

Guest favourite

Cabin in Sadieville

4.97 out of 5 average rating, 249 reviews

*Unique Country Cabin *1BR 20 min from The Ark!

No neighbors! It’s not a big or fancy place but it’s clean, simple, and relaxing. The stars are brightest in the country when enjoying the fire pit. Our two story cabin has 1BR with two double beds, full kitchen, full bathroom, recliners, and grills. It's perfect for couples, friends, or small families. The Ark Encounter, Kentucky Horse Park, Keeneland, and several distilleries are all within an hour of the cabin. This is a great place to relax between visits to these attractions.

11 – 18 Mar

$1,185 AUD total

Guest favourite

Home in Paris

4.95 out of 5 average rating, 154 reviews

The Spring Valley Inn - charming rural home

Nestled only 4 miles outside of historic Paris, Kentucky this charming home will allow you and your guests to immerse yourself in the beautiful surroundings of Thoroughbred horse country. On your drive to the home pass horse farms such as Oak Lodge, Brandywine, and Adena Springs; all recognizable names from past Kentucky Derby runners. Enjoy your stay with room for your family not only indoors but out. Sit on the patio soaking in nature and local sounds from neighboring farm animals.

4 – 11 Jan

$1,674 AUD total

Guest favourite

Farm stay in Paris

5.0 out of 5 average rating, 5 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.

12 – 19 Dec

$1,789 AUD total

Guest favourite

Barn in Paris

4.94 out of 5 average rating, 64 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.

11 – 16 Jan

$1,341 AUD total

Guest favourite

Home in Winchester

4.91 out of 5 average rating, 676 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 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.

17 – 24 July

$688 AUD total

Guest favourite

Bungalow in Dry Ridge

4.97 out of 5 average rating, 576 reviews

The Cute Little House Near The Ark Encounter

The "Little House" is a cute 1 bedroom house located on our farm in a beautiful country setting with 6 acres of outdoor space for relaxing. It is separate from our home and is all yours. It is conveniently located only 8 miles from the Ark Encounter and you only need to make one turn to get there. We have chickens, ducks, rabbits, a horse, and 2 goats. We also have a 1/2 mile nature trail to explore with a scavenger hunt, and a campfire spot with free firewood.

22 – 29 Oct

$1,271 AUD total

Guest favourite

Guesthouse in Winchester

4.98 out of 5 average rating, 176 reviews

Escape and unwind in the country

Relax and unwind in the country! Close to Lexington, Red River Gorge, Pilot Knob and Natural Bridge with easy access to the Mountain Parkway. We now have Wi-Fi!! Pets are welcome but we request that dogs are either crated or not left unattended. There is a $25 pet cleaning fee. Our guest house has a fully equipped kitchen, washer/dryer, queen size Sleep Number Bed, queen size sleeper sofa, and patio with gas grill. An air mattress is available by request.

23 – 30 Apr

$862 AUD total

Guest favourite

Barn in Lexington

4.94 out of 5 average rating, 294 reviews

Stay with our horses and goats on a private farm

Lovely and private studio barn apartment in super safe neighborhood. Stay with our horse and goats on 12 private acres, minutes from downtown Lexington. Hiking trails around property, and just minutes to several state parks. Three miles to 75 and 64, and 15 minutes to downtown Lexington, the Kentucky Horse Park, UK campus, and 10 minutes to the Hamburg area of Lexington full of restaurants, sports bars, and movie theaters. 50 amp EV charging station

4 – 11 Jan

$1,080 AUD total

Guest favourite

Farm stay in Carlisle

4.99 out of 5 average rating, 122 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.

16 – 23 Feb

$1,871 AUD total