North Middletown Vacation Rentals

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Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

Our top choices for North Middletown vacation rentals

Property grounds

Cozy, Bright Home in Historic Downtown

Cozy, Bright Home in Historic Downtown
Mount Sterling
8.4 out of 10, Very Good, (22 reviews)
"We did not stay. Nothing had been cleaned. Asked for a refund"
United States
Ginger
The price is ￥10,043
￥19,858 total
includes taxes & fees
May 3 - May 4
Cozy, Bright Home in Historic Downtown
Private kitchen

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

‘Edith’ Carriage House Getaway - Hamburg/I-75!
Lexington
9.0 out of 10, Wonderful, (2 reviews)
"Had a pleasant stay ! Thanks "
United States
brenda s.
The price is ￥6,887
￥21,130 total
includes taxes & fees
May 11 - May 12
‘Edith’ Carriage House Getaway - Hamburg/I-75!
Exterior

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.
The price is ￥15,782
￥20,913 total
includes taxes & fees
May 4 - May 5
1 Bedroom Bourbon House on the Hill
Iron/ironing board, WiFi, bed sheets

5 o'clock somewhere in Mt Sterling

5 o'clock somewhere in Mt Sterling
Mount Sterling
8.0 out of 10, Very Good, (1 review)
"A good stay in a friendly area."
United States
Trey S.
The price is ￥16,499
￥21,705 total
includes taxes & fees
Apr 30 - May 1
5 o'clock somewhere in Mt Sterling
Private kitchen

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

The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling
Mount Sterling
The price is ￥20,245
￥25,832 total
includes taxes & fees
May 23 - May 24
The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling
Terrace/patio

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

Charming Cottage - Near I-75 & Horse Park + Farms
Lexington
10.0 out of 10, Exceptional, (1 review)
"Everything was perfect for our family. Great communication with host."
United States
Scooby D.
The price is ￥14,023
￥45,881 total
includes taxes & fees
May 11 - May 12
Charming Cottage - Near I-75 & Horse Park + Farms
Outdoor dining

Spacious King Suite | Horses, Fire Pit, Garage

Spacious King Suite | Horses, Fire Pit, Garage
Lexington
9.8 out of 10, Exceptional, (24 reviews)
"Great space "
United States
Russell
The price is ￥18,061
￥53,297 total
includes taxes & fees
May 5 - May 6
Spacious King Suite | Horses, Fire Pit, Garage
Property grounds

Midnight Lexington Newly Remodeled Designer Stay

Midnight Lexington Newly Remodeled Designer Stay
Lexington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location. Great home with all the conveniences. Easy to access and good beds. We would stay here again!"
United States
Rebecca N.
The price is ￥20,803
￥61,708 total
includes taxes & fees
May 10 - May 11
Midnight Lexington Newly Remodeled Designer Stay
Fridge, microwave, oven, stovetop

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, (7 reviews)
"Very homey place to stay! Nice neighborhood!"
United States
Tim T.
The price is ￥23,672
￥48,593 total
includes taxes & fees
Apr 30 - May 1
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
Terrace/patio

Relaxing Hot Tub | S’mores Fire Pit | Garage

Relaxing Hot Tub | S’mores Fire Pit | Garage
LEXINGTON
9.2 out of 10, Wonderful, (48 reviews)
"Communication with the host was very timely, and all accommodations were clean and working. We had a great stay!"
United States
Francesca A.
The price is ￥18,731
￥47,900 total
includes taxes & fees
May 10 - May 11
Relaxing Hot Tub | S’mores Fire Pit | Garage
Exterior

River Relaxation - Calm Riverfront Home in Winchester Kentucky

River Relaxation - Calm Riverfront Home in Winchester Kentucky
Winchester
7.0 out of 10, Good, (4 reviews)
"We loved the house, the hosts were great and super communicative! The house is also close to Lexington and Winchester so we had plenty to do and places to eat out! "
United States
Maeve R.
The price is ￥25,507
￥67,348 total
includes taxes & fees
May 3 - May 4
River Relaxation - Calm Riverfront Home in Winchester Kentucky
Exterior detail

Cabin in Kentucky Horse Country

Cabin in Kentucky Horse Country
Bourbon County
10.0 out of 10, Exceptional, (81 reviews)
"Beautiful property and great host. Paris is a quaint town but plenty of activities to do. "
United Kingdom
Brandon K.
The price is ￥51,808
￥77,953 total
includes taxes & fees
Apr 30 - May 1
Cabin in Kentucky Horse Country
Fridge, microwave, oven, stovetop

Modern Barndo, Hot Tub, Sauna, Fire Pit, 20 min RRG, Rec Room, Pickleball

Modern Barndo, Hot Tub, Sauna, Fire Pit, 20 min RRG, Rec Room, Pickleball
Powell County
10.0 out of 10, Exceptional, (11 reviews)
"Great location, tons of things to do, and just about 20-25 min from the gorge."
United States
Veeresh R.
The price is ￥51,453
￥109,319 total
includes taxes & fees
May 5 - May 6
Modern Barndo, Hot Tub, Sauna, Fire Pit, 20 min RRG, Rec Room, Pickleball
Dining

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
10.0 out of 10, Exceptional, (3 reviews)
"We traveled to the area for the breeders cup. The house was really nice and comfortable. The ride getting there was beautiful country. House was as described. Worth the cost. We had a great time. Would definitely stay there again when we return to the Lexington area."
United States
marty e.
The price is ￥31,723
￥70,018 total
includes taxes & fees
May 4 - May 5
The Williams House by Mustard Seed Hill - A Cozy Bourbon County Getaway

The Winchester

The Winchester
Winchester
8.4 out of 10, Very Good, (7 reviews)
"I rented this house for my bridesmaids. It was a great location and house. The owner was accommodating and replied quickly "
United States
Karissa A.
The price is ￥21,542
￥46,615 total
includes taxes & fees
May 7 - May 8
The Winchester
Exterior

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 ￥26,303
￥51,941 total
includes taxes & fees
May 11 - May 12
Helena's Cottage: Romantic, Cozy Getaway with Lavish King Bed, Gas Fireplace
Living area

The Parsonage of Paris

The Parsonage of Paris
Paris
10.0 out of 10, Exceptional, (1 review)
"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 ￥35,867
￥62,823 total
includes taxes & fees
Apr 30 - May 1
The Parsonage of Paris
Exterior

Hunting Lodge in the City

Hunting Lodge in the City
Mount Sterling
The price is ￥17,216
￥22,494 total
includes taxes & fees
Apr 30 - May 1
Hunting Lodge in the City
Interior

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, (1 review)
"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.
The price is ￥45,910
￥101,764 total
includes taxes & fees
May 11 - May 12
Fully Furnished 4BR Home in Lexington Short & Mid-Term
Exterior

The Parsonage: A Grand 19th Century 4 Bedroom Home

The Parsonage: A Grand 19th Century 4 Bedroom Home
Millersburg
The price is ￥41,287
￥80,017 total
includes taxes & fees
Apr 30 - May 1
The Parsonage: A Grand 19th Century 4 Bedroom Home
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

Hampton Inn I-75 Lexington/Hamburg Area

Hampton Inn I-75 Lexington/Hamburg Area

6/10 Okay
"Didn’t use the free breakfast so we can’t comment on that but the staff was helpful and friendly. The air conditioning unit was noisy and beyond our control a thunderstorm was going on through the night and people’s dogs were going crazy. These things DIDNT contribute to a good nights sleep. The bed was comfortable and clean though."
Kristine 1-night trip
Posted 2 hours ago
Hampton Inn I-75 Lexington/Hamburg Area

Find out more about North Middletown

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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?

Lovely 3 Bdrm Home w/Free Parking Close to I-75!: This vacation home rental outside of North Middletown offers a patio, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What can I see and do in North Middletown?

While you're exploring the area, Lykins Park and Winchester Traveling Trail 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.