North Middletown Vacation Rentals

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Check prices for these dates

In two weeks
May 8 - May 10
In two months
Jun 19 - Jun 21
In three months
Jul 17 - Jul 19
In four months
Aug 14 - Aug 16

Our top choices for North Middletown vacation rentals

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 ￥7,655
￥22,027 total
includes taxes & fees
May 10 - May 11
‘Edith’ Carriage House Getaway - Hamburg/I-75!
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 ￥10,047
￥19,866 total
includes taxes & fees
Apr 27 - Apr 28
Cozy, Bright Home in Historic Downtown
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 ￥15,789
￥20,923 total
includes taxes & fees
Apr 24 - Apr 25
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 ￥16,506
￥21,715 total
includes taxes & fees
Apr 27 - Apr 28
5 o'clock somewhere in Mt Sterling
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 ￥15,350
￥53,772 total
includes taxes & fees
Apr 28 - Apr 29
Spacious King Suite | Horses, Fire Pit, Garage
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 ￥18,229
￥23,611 total
includes taxes & fees
Apr 24 - Apr 25
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 ￥14,029
￥45,901 total
includes taxes & fees
Apr 28 - Apr 29
Charming Cottage - Near I-75 & Horse Park + Farms
Exterior

Hunting Lodge in the City

Hunting Lodge in the City
Mount Sterling
The price is ￥17,224
￥22,504 total
includes taxes & fees
Apr 24 - Apr 25
Hunting Lodge in the City
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 ￥20,812
￥61,735 total
includes taxes & fees
Apr 28 - Apr 29
Midnight Lexington Newly Remodeled Designer Stay
Exterior detail

Cabin in Kentucky Horse Country

Cabin in Kentucky Horse Country
Bourbon County
10.0 out of 10, Exceptional, (81 reviews)
"The cabin was unique if only for its location on the farm. It was as secure as we could have asked for. A definite gem. "
United States
Vickie B.
The price is ￥51,831
￥77,987 total
includes taxes & fees
Apr 26 - Apr 27
Cabin in Kentucky Horse Country
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.
River Relaxation - Calm Riverfront Home in Winchester Kentucky
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 ￥52,585
￥110,728 total
includes taxes & fees
Apr 28 - Apr 29
Modern Barndo, Hot Tub, Sauna, Fire Pit, 20 min RRG, Rec Room, Pickleball
Interior

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

Fully Furnished 4BR Home in Lexington Short & Mid-Term
Lexington
The price is ￥45,930
￥101,809 total
includes taxes & fees
May 6 - May 7
Fully Furnished 4BR Home in Lexington Short & Mid-Term
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 ￥21,530
￥51,330 total
includes taxes & fees
May 10 - May 11
Relaxing Hot Tub | S’mores Fire Pit | Garage
Fridge, microwave, oven, stovetop

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 ￥42,900
￥81,984 total
includes taxes & fees
Apr 28 - Apr 29
Historical 1812 Home featuring a Chef's Kitchen, Laundry, and AC
Exterior detail

The Neal House: Charming & Historic 3 Bedroom House

The Neal House: Charming & Historic 3 Bedroom House
Millersburg
The price is ￥36,521
￥74,260 total
includes taxes & fees
Apr 28 - Apr 29
The Neal House: Charming & Historic 3 Bedroom House
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 ￥26,314
￥51,963 total
includes taxes & fees
Apr 28 - Apr 29
Helena's Cottage: Romantic, Cozy Getaway with Lavish King Bed, Gas Fireplace
Exterior

The Parsonage: A Grand 19th Century 4 Bedroom Home

The Parsonage: A Grand 19th Century 4 Bedroom Home
Millersburg
The price is ￥41,305
￥80,052 total
includes taxes & fees
Apr 28 - Apr 29
The Parsonage: A Grand 19th Century 4 Bedroom Home
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 ￥23,683
￥49,141 total
includes taxes & fees
Apr 26 - Apr 27
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

The Winchester

The Winchester
Winchester
8.4 out of 10, Very Good, (7 reviews)
The price is ￥21,530
￥46,589 total
includes taxes & fees
May 7 - May 8
The Winchester
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

Fairfield Inn & Suites by Marriott Lexington East/I-75

Fairfield Inn & Suites by Marriott Lexington East/I-75

10/10 Excellent
"Extremely friendly and helpfull staff. Felt very welcome and appreciated "
Dave 1-night trip
Posted 1 hour ago
Fairfield Inn & Suites by Marriott Lexington East/I-75

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.