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North Middletown Vacation Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for North Middletown vacation rentals

A Farmers' Market pavilion with a clear roof, a sign indicating it's powered by KJ, and operating hours from June through October.

1. Cozy, Bright Home in Historic Downtown

Cozy, Bright Home in Historic Downtown
Mount Sterling
8.4 out of 10, Very good, (25 reviews)
"This is definitely an older home, but it was clean and comfortable and the Dolly memorabilia is amazing!"
United States
Glenda
The price is AED 231
AED 425 total
includes taxes & fees
8 Nov - 9 Nov
Cozy, Bright Home in Historic Downtown
A bedroom with a bed, nightstands, a ceiling fan, a mural of a sunset, and a window with blinds.

2. 5 o'clock somewhere in Mt Sterling

5 o'clock somewhere in Mt Sterling
Mount Sterling
9.0 out of 10, Wonderful, (4 reviews)
"A good stay in a friendly area."
United States
Trey S.
The price is AED 380
AED 468 total
includes taxes & fees
8 Nov - 9 Nov
5 o'clock somewhere in Mt Sterling
Exterior

3. Hunting Lodge in the City

Hunting Lodge in the City
Mount Sterling
The price is AED 397
AED 486 total
includes taxes & fees
8 Nov - 9 Nov
Hunting Lodge in the City
Private kitchen

4. The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling

The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling
Mount Sterling
10.0 out of 10, Exceptional, (3 reviews)
"Very easy check in and nice location"
United States
Robert G.
The price is AED 466
AED 563 total
includes taxes & fees
30 Nov - 1 Dec
The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling
A two-story house with a porch and a front yard.

5. Charming Victorian Apartment | Downtown Winchester

Charming Victorian Apartment | Downtown Winchester
Winchester
The price is AED 268
AED 1,480 total
includes taxes & fees
16 Nov - 17 Nov
Charming Victorian Apartment | Downtown Winchester
A kitchen with white cabinets, a stainless steel oven, and a dishwasher.

6. 4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
Winchester
9.6 out of 10, Exceptional, (14 reviews)
"Very homey place to stay! Nice neighborhood!"
United States
Tim T.
The price is AED 496
AED 1,024 total
includes taxes & fees
21 Nov - 22 Nov
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
A rural road curving through a green landscape with a wooden fence, a stone wall, and a small building in the distance.

7. Historical 4-bedroom farmhouse in serene Sharpsburg with AC.

Historical 4-bedroom farmhouse in serene Sharpsburg with AC.
Sharpsburg
9.6 out of 10, Exceptional, (9 reviews)
"We had a great time with the family."
United States
Garrett W.
The price is AED 826
AED 1,518 total
includes taxes & fees
9 Nov - 10 Nov
Historical 4-bedroom farmhouse in serene Sharpsburg with AC.
A black leather sofa with a center console, a glass table, and two boxes on the table.

8. The Winchester

The Winchester
Winchester
8.6 out of 10, Excellent, (11 reviews)
"The house was clean and had all amenities needed. Love the location and was adorable. Wish I could have stayed longer. Love that there is a park across the street and the neighbors were very friendly"
United States
Gina
The price is AED 496
AED 1,024 total
includes taxes & fees
9 Nov - 10 Nov
The Winchester
A log cabin bedroom with a four-poster bed, a leather armchair, and a fur rug.

9. Cabin in Kentucky Horse Country

Cabin in Kentucky Horse Country
Bourbon County
10.0 out of 10, Exceptional, (82 reviews)
"Beautiful cabin with wonderful views in a peaceful setting"
United Kingdom
Siobann S.
The price is AED 1,194
AED 1,707 total
includes taxes & fees
8 Nov - 9 Nov
Cabin in Kentucky Horse Country
A living room with a blue sofa set, a wooden coffee table, and a chandelier.

10. The Parsonage of Paris

The Parsonage of Paris
Paris
6.0 out of 10, (2 reviews)
"This is a very nice place....clean, well-decorated, great air conditioning and a nice quiet location in downtown Paris. Enjoyed our stay!"
United States
Leslie S.
The price is AED 702
AED 1,210 total
includes taxes & fees
14 Nov - 15 Nov
The Parsonage of Paris
A dining room with a wooden table and chairs, a chandelier, a fireplace, and a mirror on the wall.

11. The Williams House by Mustard Seed Hill - A Cozy Bourbon County Getaway

The Williams House by Mustard Seed Hill - A Cozy Bourbon County Getaway
Paris
8.8 out of 10, Excellent, (5 reviews)
"This property is an older home remodeled. the showers are only for SMALL people. they use horrible smelling air freshners. it took 2 days to get the chemical smell out. And the lights in the bathroom went out after the first day. The price on this home is way to high for the property. But on a good note, the fenced in back yard is huge. the dogs loved it. but the next door neighbor has aggressive pit bulls who go nuts at the fence when they are out. . And after letting the owner know about the...
United States
Randy H.
The price is AED 735
AED 1,536 total
includes taxes & fees
8 Nov - 9 Nov
The Williams House by Mustard Seed Hill - A Cozy Bourbon County Getaway
An outdoor patio area with a fire pit, wicker furniture, and a pool.

12. Bluegrass Bourbon Retreat/Pool/ Downtown Paris

Bluegrass Bourbon Retreat/Pool/ Downtown Paris
Paris
The price is AED 946
AED 2,532 total
includes taxes & fees
8 Nov - 9 Nov
Bluegrass Bourbon Retreat/Pool/ Downtown Paris
A house with a blue door, two windows with shutters, and a porch with a white railing.

13. Helena's Cottage: Romantic, Cozy Getaway with Lavish King Bed, Gas Fireplace

Helena's Cottage: Romantic, Cozy Getaway with Lavish King Bed, Gas Fireplace
Millersburg
Helena's Cottage: Romantic, Cozy Getaway with Lavish King Bed, Gas Fireplace
A doorway leading to a room with a patterned chair and a painting on the wall.

14. Charming Apartment in the Heart of Carlisle

Charming Apartment in the Heart of Carlisle
Carlisle
10.0 out of 10, Exceptional, (1 review)
"This is the cutest place to stay in a very welcoming community. Loved how the town was all decorated for fall and Halloween."
United States
Stephanie D.
The price is AED 624
AED 979 total
includes taxes & fees
9 Nov - 10 Nov
Charming Apartment in the Heart of Carlisle
A two-story house with a beige exterior, numbered 1112, featuring a front porch with two wicker chairs and two wall-mounted lanterns.

15. The Neal House: Charming & Historic 3 Bedroom House

The Neal House: Charming & Historic 3 Bedroom House
Millersburg
The Neal House: Charming & Historic 3 Bedroom House
A two-story wooden cabin with a balcony, surrounded by trees.

16. River Relaxation - Calm Riverfront Home in Winchester Kentucky

River Relaxation - Calm Riverfront Home in Winchester Kentucky
Winchester
8.0 out of 10, Very good, (7 reviews)
"Good communication, great location and peaceful! Back deck to River does need a little work but it was overall a good stay! "
United States
Polly H.
The price is AED 425
AED 1,278 total
includes taxes & fees
8 Nov - 9 Nov
River Relaxation - Calm Riverfront Home in Winchester Kentucky
A kitchen with a central island, two pendant lights, a stove, and wooden cabinets.

17. Historical 1812 Home featuring a Chef's Kitchen, Laundry, and AC

Historical 1812 Home featuring a Chef's Kitchen, Laundry, and AC
Millersburg
10.0 out of 10, Exceptional, (1 review)
"This property is perfect for families traveling together. Each bedroom has its own bathroom and plenty of room for everyone to relax. The kitchen is perfect and the back porch makes a great place to have your coffee in the morning or in the evening. It’s only 20 minutes from Cynthia Anna and less than 10 minutes from Paris, so if you were looking for a great place to stay look no further! We had an issue with one of the beds and they took care of it within a few hours"
United States
Michelle
Historical 1812 Home featuring a Chef's Kitchen, Laundry, and AC
A two-story house with a front porch, a central door, and a small front yard.

18. The Parsonage: A Grand 19th Century 4 Bedroom Home

The Parsonage: A Grand 19th Century 4 Bedroom Home
Millersburg
The Parsonage: A Grand 19th Century 4 Bedroom Home
A house with a covered porch, string lights, and a lawn.

19. Charming Cottage - Near I-75 & Horse Park + Farms

Charming Cottage - Near I-75 & Horse Park + Farms
Lexington
9.6 out of 10, Exceptional, (7 reviews)
"Everything was perfect for our family. Great communication with host."
United States
Scooby D.
Charming Cottage - Near I-75 & Horse Park + Farms
A hot tub with two people and a bar area with bottles and a lantern.

20. Relaxing Hot Tub | S’mores Fire Pit | Garage

Relaxing Hot Tub | S’mores Fire Pit | Garage
LEXINGTON
9.4 out of 10, Exceptional, (55 reviews)
"Great stay will think of this place if we ever go back to lexington"
United States
Stephanie S.
The price is AED 432
AED 1,112 total
includes taxes & fees
12 Nov - 13 Nov
Relaxing Hot Tub | S’mores Fire Pit | Garage
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top North Middletown Hotel Reviews

Microtel Inn by Wyndham Lexington

Microtel Inn by Wyndham Lexington

10/10 Excellent
"Good"
Nelson 1-night trip
Posted 5 hours ago
Microtel Inn by Wyndham Lexington

Frequently asked questions

Can I find a vacation rental in North Middletown?

Yes, we offer vacation rentals near top local attractions in North Middletown, or you can go with a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental that North Middletown has to offer?

Renovated train station on thoroughbred horse farm.: This vacation home rental outside of North Middletown is located in the city center and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What can I see and do in North Middletown?

While you're exploring the area, Lake Carnico and College Park are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find The Cane Ridge Meeting House and Claiborne Farm.

What are vacation rentals like in North Middletown?

Vacation rentals are private accommodations you can book for a few days or a quick weekend in North Middletown. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for family trips or small group gatherings.