Holiday rentals in North Middletown

4.92 out of 5 average rating, 151 reviews

Farm stay in Winchester

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.

4.99 out of 5 average rating, 157 reviews

Farm stay in Ewing

Haymark Farmhouse: cozy & clean, with outdoor fun!

Welcome to Haymark Farmhouse, built in 1907. Relax in front of the fireplace with electric logs, play games (provided), and cook in the well-supplied kitchen or on the gas grill out back. Enjoy the outdoor fire pit (wood provided) and the lighted sitting area and table for eight. Explore our 275 acre farm! Pet our cute farm animals, take a hike along the creek, catch a fish in the pond, hunt (message us for rates), watch a sunset ... If you need room for more folks, check out Thomas Road House.

4.95 out of 5 average rating, 84 reviews

Cabin in Paris

1791 Cabin on Historic Horse Farm

This rare 1791 log cabin is located on Houstondale Farm, a working horse farm in the renowned Bluegrass region of Ky. You can stroll to the barn and visit the horses or enjoy the peace and quiet before relaxing at the pool, complete with a grill and outdoor dining area. It is a scenic 22 minute drive from the Ky Horse Park, 25 minutes from Lexington, and 30 minutes from Keeneland Race Track. Even with the remote feel of the farm you will only be a mile from Walmart, shops & downtown Paris.

4.9 out of 5 average rating, 84 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.

4.97 out of 5 average rating, 367 reviews

Cabin in McKee

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 house in Winchester

4.93 out of 5 average rating, 198 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.

4.93 out of 5 average rating, 220 reviews

Treehouse in Georgetown

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

4.91 out of 5 average rating, 809 reviews

Home in Winchester

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.

4.95 out of 5 average rating, 88 reviews

Barn in Paris

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

4.82 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.

4.89 out of 5 average rating, 151 reviews

Flat in Winchester

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. After your hike (or whenever, you are on vacation), visit the Waterfront Grill or Hall’s on the River. They offer dining, bar, and seasonal outdoor seating. They are about a half mile down the road from the cottage. A tasting at the winery just a few minutes away will sweeten your stay. For more play, kayak rental is nearby.

4.94 out of 5 average rating, 114 reviews

Apartment in Paris

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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Other great holiday rentals in North Middletown

Superhost

Home in Winchester

4.85 out of 5 average rating, 33 reviews

The Winchester

BrigetteRating, 5 stars3 weeks ago

We had family in town for my son's graduation and Wayne's place was perfect for our accommodations. It was just like being at home. We enjoyed the layout of the house, the backyard and closeness to everything. Wayne was a fantastic host. Very friendly and accommodating. He even helped me get information on the graduation. I hope to stay there again in the future.

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!!

4.9 out of 5 average rating, 177 reviews

The Spring Valley Inn - charming rural home

LoriRating, 5 stars2 weeks ago

We stayed here to attend a concert in Lexington. Was a nice landing place. Quiet. Not far from town. Affordable and comfortable. Beautiful property and drive there. I'd recommend this house to stay in.

4.95 out of 5 average rating, 59 reviews

Cabin in Frenchburg

Ridge-Top Retreat | Cozy Cabin w/Hot Tub

CodiRating, 5 stars6 days ago

Such a sweet and responsive host! Not to mention the beautiful cabin. Highly highly recommended! Will be coming back. 💕

4.93 out of 5 average rating, 43 reviews

Home in Winchester

Cute 2 Story Home in Winchester

MaggieRating, 5 stars3 weeks ago

We were in town for a wedding and this place was perfect! Jacqueline was responsive and very helpful with a few questions we had.

5 out of 5 average rating, 26 reviews

Tiny home in Ewing

The Cottage at Stillhouse Cabin

SethRating, 5 stars3 weeks ago

we needed a place to stay last minute and Carol came through. She got the cabin cleaned up and had it ready for us to stay in and helped us out tremendously. great find and would absolutely stay there again.

Home in Mount Sterling

4.73 out of 5 average rating, 45 reviews

Magnolia bluff

KimberlyRating, 5 stars3 weeks ago

The location is convenient to the freeway, restaurants, and grocery stores. Great for those on the go and then needing a comfy home away from home. Tony delivered and made sure we didn’t want for anything to make our stay even better!! I’ll definitely be back when in the area!

Superhost