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North Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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 ￥9,883
￥19,541 total
includes taxes & fees
Oct 26 - Oct 27
Cozy, Bright Home in Historic Downtown
A building with a staircase leading to a door marked with the number 218.

2. 1 Bedroom Bourbon House on the Hill

1 Bedroom Bourbon House on the Hill
Mount Sterling
10.0 out of 10, Exceptional, (2 reviews)
"This property was very welcoming to our small dog."
United States
Anne D.
The price is ￥15,530
￥20,580 total
includes taxes & fees
Oct 31 - Nov 1
1 Bedroom Bourbon House on the Hill
A bedroom with a bed, a chair, a wooden cabinet, and a door leading to another room.

3. 2nd Story Historic Downtown 2BR with Modern Amenities

2nd Story Historic Downtown 2BR with Modern Amenities
Winchester
9.0 out of 10, Wonderful, (13 reviews)
"We had a great stay, the unit has lots of charm and is very cozy. We enjoyed the walkability to great local shops and restaurants. It's within a short driving distance to other great areas to check out!"
United States
Brian M.
2nd Story Historic Downtown 2BR with Modern Amenities
A bedroom with a bed, nightstands, a ceiling fan, a mural of a sunset, and a window with blinds.

4. 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 ￥16,236
￥21,359 total
includes taxes & fees
Oct 26 - Oct 27
5 o'clock somewhere in Mt Sterling
A kitchen with white cabinets, a black countertop, and a patterned rug.

5. ‘Edith’ Carriage House Getaway - Hamburg/I-75!

‘Edith’ Carriage House Getaway - Hamburg/I-75!
Lexington
8.8 out of 10, Excellent, (6 reviews)
"A great one night stay! Plenty of room. Nice kitchen area and outside deck."
United States
Kevin P.
The price is ￥7,844
￥22,577 total
includes taxes & fees
Nov 1 - Nov 2
‘Edith’ Carriage House Getaway - Hamburg/I-75!
A rural road curving through a green landscape with a wooden fence, a stone wall, and a small building in the distance.

6. 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 ￥35,296
￥68,137 total
includes taxes & fees
Oct 28 - Oct 29
Historical 4-bedroom farmhouse in serene Sharpsburg with AC.
A kitchen with white cabinets, a stainless steel oven, and a dishwasher.

7. 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 ￥21,177
￥45,826 total
includes taxes & fees
Nov 1 - Nov 2
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
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 ￥21,177
￥45,826 total
includes taxes & fees
Oct 26 - Oct 27
The Winchester
Exterior

9. Hunting Lodge in the City

Hunting Lodge in the City
Mount Sterling
The price is ￥18,824
￥24,211 total
includes taxes & fees
Nov 17 - Nov 18
Hunting Lodge in the City
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 ￥22,001
￥48,008 total
includes taxes & fees
Oct 26 - Oct 27
The Parsonage of Paris
A doorway leading to a room with a patterned chair and a painting on the wall.

11. 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 ￥26,668
￥43,833 total
includes taxes & fees
Oct 26 - Oct 27
Charming Apartment in the Heart of Carlisle
A gated entrance with a stone wall, a tree, and white hydrangea flowers.

12. 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 ￥50,983
￥76,711 total
includes taxes & fees
Oct 26 - Oct 27
Cabin in Kentucky Horse Country
A dining room with a wooden table and chairs, a chandelier, a fireplace, and a mirror on the wall.

13. 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 ￥31,374
￥69,075 total
includes taxes & fees
Nov 1 - Nov 2
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.

14. Bluegrass Bourbon Retreat/Pool/ Downtown Paris

Bluegrass Bourbon Retreat/Pool/ Downtown Paris
Paris
The price is ￥35,578
￥102,489 total
includes taxes & fees
Nov 16 - Nov 17
Bluegrass Bourbon Retreat/Pool/ Downtown Paris
A house with a blue door, two windows with shutters, and a porch with a white railing.

15. 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
The price is ￥29,021
￥56,296 total
includes taxes & fees
Nov 1 - Nov 2
Helena's Cottage: Romantic, Cozy Getaway with Lavish King Bed, Gas Fireplace
A two-story house with a beige exterior, numbered 1112, featuring a front porch with two wicker chairs and two wall-mounted lanterns.

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

The Neal House: Charming & Historic 3 Bedroom House
Millersburg
The price is ￥39,061
￥78,746 total
includes taxes & fees
Nov 1 - Nov 2
The Neal House: Charming & Historic 3 Bedroom House
A two-story house with a front porch, a central door, and a small front yard.

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

The Parsonage: A Grand 19th Century 4 Bedroom Home
Millersburg
The price is ￥43,767
￥84,618 total
includes taxes & fees
Nov 1 - Nov 2
The Parsonage: A Grand 19th Century 4 Bedroom Home
A kitchen with a central island, two pendant lights, a stove, and wooden cabinets.

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

Historical 1812 Home featuring a Chef's Kitchen, Laundry, and AC
Millersburg
The price is ￥45,335
￥86,688 total
includes taxes & fees
Nov 3 - Nov 4
Historical 1812 Home featuring a Chef's Kitchen, Laundry, and AC
A staircase with a brick wall and a painted sheep mural.

19. Marvelous 3-bedroom second floor apartment in Carlisle with lots of history

Marvelous 3-bedroom second floor apartment in Carlisle with lots of history
Carlisle
10.0 out of 10, Exceptional, (1 review)
"Location was perfect for what we needed. It was exceptionally clean which is much appreciated."
United States
caseycycling
The price is ￥26,668
￥46,184 total
includes taxes & fees
Oct 26 - Oct 27
Marvelous 3-bedroom second floor apartment in Carlisle with lots of history
A two-story house with a covered patio area, string lights, and outdoor furniture.

20. Spacious King Suite w/ Game Room, Fire Pit & Patio

Spacious King Suite w/ Game Room, Fire Pit & Patio
Lexington
9.6 out of 10, Exceptional, (29 reviews)
"Excellent location and wonderful host. The home is inviting and welcoming, perfect for a family. We had a great experience "
United States
Cassidy D.
The price is ￥21,000
￥60,618 total
includes taxes & fees
Nov 2 - Nov 3
Spacious King Suite w/ Game Room, Fire Pit & Patio
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

GuestHouse Lexington

GuestHouse Lexington

8/10 Good
"N/A"
SM Redwan 1-night trip
Posted 2 hours ago
GuestHouse Lexington

Find out more about North Middletown

Search for holiday rentals in North Middletown on Expedia! You can easily find your home rentals, villas, holiday apartments in North Middletown using one of the methods below:

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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.