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North Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for North Middletown vacation rentals

Exterior

1. 1 Bedroom Bourbon House on the Hill

1 Bedroom Bourbon House on the Hill
Mount Sterling
10.0 out of 10, Exceptional, (1 review)
"This property was very welcoming to our small dog."
United States
Anne D.
$119 nightly
The price is $131
Sep 7 - Sep 8
Total with taxes and fees
1 Bedroom Bourbon House on the Hill
Private kitchen

2. 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, (1 review)
"Everything was perfect!"
United States
Miguel
$134 nightly
The price is $148
Sep 7 - Sep 8
Total with taxes and fees
The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling
1 bedroom, iron/ironing board, WiFi, bed sheets

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.
$124 nightly
The price is $136
Sep 8 - Sep 9
Total with taxes and fees
5 o'clock somewhere in Mt Sterling
Exterior detail

4. Cabin in Kentucky Horse Country

Cabin in Kentucky Horse Country
Bourbon County
10.0 out of 10, Exceptional, (81 reviews)
"Beautiful cabin with wonderful views in a peaceful setting"
United Kingdom
Siobann S.
$450 nightly
The price is $489
Sep 7 - Sep 8
Total with taxes and fees
Cabin in Kentucky Horse Country
Property grounds

5. Cozy, Bright Home in Historic Downtown

Cozy, Bright Home in Historic Downtown
Mount Sterling
8.4 out of 10, Very Good, (23 reviews)
"Great stay as usual. Owners are super friendly & helpful. This was our 3rd time staying as we've made this our regular when visiting family in the area."
United States
Brittany K.
$113 nightly
The price is $125
Sep 7 - Sep 8
Total with taxes and fees
Cozy, Bright Home in Historic Downtown
Coffee/tea maker, fridge, microwave, oven

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
9.8 out of 10, Exceptional, (12 reviews)
"Very homey place to stay! Nice neighborhood!"
United States
Tim T.
$283 nightly
The price is $311
Sep 7 - Sep 8
Total with taxes and fees
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.

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
$283 nightly
The price is $311
Sep 7 - Sep 8
Total with taxes and fees
The Winchester
Private kitchen

8. ‘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.
$114 nightly
The price is $133
Sep 15 - Sep 16
Total with taxes and fees
‘Edith’ Carriage House Getaway - Hamburg/I-75!
Coffee/tea maker, fridge, microwave, oven

9. Bluegrass Bourbon Retreat/Pool/ Downtown Paris

Bluegrass Bourbon Retreat/Pool/ Downtown Paris
Paris
$655 nightly
The price is $720
Sep 8 - Sep 9
Total with taxes and fees
Bluegrass Bourbon Retreat/Pool/ Downtown Paris
Dining

10. 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.
$490 nightly
The price is $539
Sep 13 - Sep 14
Total with taxes and fees
The Williams House by Mustard Seed Hill - A Cozy Bourbon County Getaway
Exterior

11. Hunting Lodge in the City

Hunting Lodge in the City
Mount Sterling
$128 nightly
The price is $141
Sep 27 - Sep 28
Total with taxes and fees
Hunting Lodge in the City
Exterior detail

12. 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
$383 nightly
The price is $422
Sep 7 - Sep 8
Total with taxes and fees
Helena's Cottage: Romantic, Cozy Getaway with Lavish King Bed, Gas Fireplace
Exterior detail

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

The Neal House: Charming & Historic 3 Bedroom House
Millersburg
$548 nightly
The price is $603
Sep 7 - Sep 8
Total with taxes and fees
The Neal House: Charming & Historic 3 Bedroom House
TV

14. 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.
$568 nightly
The price is $574
Oct 7 - Oct 8
Total with taxes and fees
The Parsonage of Paris
Terrace/patio

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

Relaxing Hot Tub | S’mores Fire Pit | Garage
LEXINGTON
9.4 out of 10, Exceptional, (54 reviews)
"Stay was fine. Location is good."
United States
Lori M.
$211 nightly
The price is $244
Sep 7 - Sep 8
Total with taxes and fees
Relaxing Hot Tub | S’mores Fire Pit | Garage
Exterior

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

The Parsonage: A Grand 19th Century 4 Bedroom Home
Millersburg
$574 nightly
The price is $632
Sep 7 - Sep 8
Total with taxes and fees
The Parsonage: A Grand 19th Century 4 Bedroom Home
Coffee/tea maker, fridge, microwave, oven

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

Historical 1812 Home featuring a Chef's Kitchen, Laundry, and AC
Millersburg
$585 nightly
The price is $644
Sep 7 - Sep 8
Total with taxes and fees
Historical 1812 Home featuring a Chef's Kitchen, Laundry, and AC
Coffee/tea maker, fridge, microwave, oven

18. Fully Furnished 4BR Home in Lexington Short & Mid-Term

Fully Furnished 4BR Home in Lexington Short & Mid-Term
Lexington
10.0 out of 10, Exceptional, (2 reviews)
"Very family friendly. This was a great place for a group reunion. It was clean, had plenty of towels, and a very inviting atmosphere.Would definitely book again."
United States
Starr G.
$550 nightly
The price is $638
Sep 7 - Sep 8
Total with taxes and fees
Fully Furnished 4BR Home in Lexington Short & Mid-Term
Outdoor dining

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, (28 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.
$337 nightly
The price is $389
Sep 14 - Sep 15
Total with taxes and fees
Spacious King Suite w/ Game Room, Fire Pit & Patio
Terrace/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, (5 reviews)
"Everything was perfect for our family. Great communication with host."
United States
Scooby D.
$552 nightly
The price is $640
Sep 11 - Sep 12
Total with taxes and fees
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

Sleep Inn Lexington

Sleep Inn Lexington

8/10 Good
"While I rated this property as "Good", it was excellent for our one night stop over on the way to Georgia. Enjoyed it so much that we stayed there again on our return trip."
John 1-night trip
Posted 1 hour ago
Sleep Inn Lexington

Find out more about North Middletown

Everything you need to know about North Middletown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the North Middletown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect North Middletown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

North Middletown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in North Middletown. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit North Middletown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $131 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on North Middletown rentals

At Expedia, we put the best North Middletown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top North Middletown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream North Middletown vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around North Middletown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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, Community Park and Lake Carnico are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Claiborne Farm and Hopewell Museum.

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.