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North Middletown Holiday Rentals

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Our top choices for North Middletown holiday rentals

1. Cozy, Bright Home in Historic Downtown

Cozy, Bright Home in Historic Downtown
Mount Sterling
8.6 out of 10, Excellent, (24 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 NZ$236
includes taxes & fees
8 Nov - 9 Nov
Cozy, Bright Home in Historic Downtown

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 NZ$234
includes taxes & fees
18 Oct - 19 Oct
1 Bedroom Bourbon House on the Hill

3. 5 o'clock somewhere in Mt Sterling

5 o'clock somewhere in Mt Sterling
Mount Sterling
9.4 out of 10, Exceptional, (3 reviews)
"A good stay in a friendly area."
United States
Trey S.
The price is NZ$243
includes taxes & fees
11 Oct - 12 Oct
5 o'clock somewhere in Mt Sterling

4. 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
9.4 out of 10, Exceptional, (13 reviews)
"Very homey place to stay! Nice neighborhood!"
United States
Tim T.
The price is NZ$519
includes taxes & fees
11 Oct - 12 Oct
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

5. 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, (8 reviews)
"Delightful country setting that allowed our family to be together to prepare for our daughter’s wedding. "
United States
Lance S.
The price is NZ$766
includes taxes & fees
23 Oct - 24 Oct
Historical 4-bedroom farmhouse in serene Sharpsburg with AC.

6. 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 NZ$845
includes taxes & fees
14 Oct - 15 Oct
Cabin in Kentucky Horse Country

7. 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 NZ$519
includes taxes & fees
13 Oct - 14 Oct
The Winchester

8. 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 NZ$507
includes taxes & fees
10 Nov - 11 Nov
Marvelous 3-bedroom second floor apartment in Carlisle with lots of history

9. Hunting Lodge in the City

Hunting Lodge in the City
Mount Sterling
Hunting Lodge in the City

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

‘Edith’ Carriage House Getaway - Hamburg/I-75!
Lexington
9.6 out of 10, Exceptional, (5 reviews)
"A great one night stay! Plenty of room. Nice kitchen area and outside deck."
United States
Kevin P.
The price is NZ$255
includes taxes & fees
8 Nov - 9 Nov
‘Edith’ Carriage House Getaway - Hamburg/I-75!

11. 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 NZ$671
includes taxes & fees
14 Oct - 15 Oct
The Parsonage of Paris

12. 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 NZ$782
includes taxes & fees
1 Nov - 2 Nov
The Williams House by Mustard Seed Hill - A Cozy Bourbon County Getaway

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
The price is NZ$627
includes taxes & fees
1 Nov - 2 Nov
Helena's Cottage: Romantic, Cozy Getaway with Lavish King Bed, Gas Fireplace

14. Bluegrass Bourbon Retreat/Pool/ Downtown Paris

Bluegrass Bourbon Retreat/Pool/ Downtown Paris
Paris
The price is NZ$1,352
includes taxes & fees
14 Oct - 15 Oct
Bluegrass Bourbon Retreat/Pool/ Downtown Paris

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

The Neal House: Charming & Historic 3 Bedroom House
Millersburg
The price is NZ$890
includes taxes & fees
1 Nov - 2 Nov
The Neal House: Charming & Historic 3 Bedroom House

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

The Parsonage: A Grand 19th Century 4 Bedroom Home
Millersburg
The price is NZ$927
includes taxes & fees
8 Nov - 9 Nov
The Parsonage: A Grand 19th Century 4 Bedroom Home

17. 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 NZ$949
includes taxes & fees
1 Nov - 2 Nov
Historical 1812 Home featuring a Chef's Kitchen, Laundry, and AC

18. Charming Apartment in the Heart of Carlisle

Charming Apartment in the Heart of Carlisle
Carlisle
The price is NZ$497
includes taxes & fees
11 Oct - 12 Oct
Charming Apartment in the Heart of Carlisle

19. 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 NZ$960
includes taxes & fees
25 Oct - 26 Oct
Spacious King Suite w/ Game Room, Fire Pit & Patio

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

Charming Cottage - Near I-75 & Horse Park + Farms
Lexington
10.0 out of 10, Exceptional, (6 reviews)
"Everything was perfect for our family. Great communication with host."
United States
Scooby D.
Charming Cottage - Near I-75 & Horse Park + Farms
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

Find out more about North Middletown

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our North Middletown holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up North Middletown. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in North Middletown. Seeing all the best attractions is bound to make you fall in love with North Middletown. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in North Middletown short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in North Middletown?

Yes, there are holiday rentals close to the most popular sights in North Middletown, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that North Middletown has to offer?

Renovated train station on thoroughbred horse farm.: This holiday home rental outside of North Middletown is located in the city centre, and has a garden, a BBQ 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 wider area, you’ll find The Cane Ridge Meeting House and Claiborne Farm.

What are holiday rentals like in North Middletown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in North Middletown. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for family gatherings.