North Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

Our top choices for North Middletown vacation rentals

Property grounds

Vacation Home in Mount Sterling

Cozy, Bright Home in Historic Downtown
8.8 out of 10, Excellent, (21 reviews)
"Our stay was perfect again! Thank you so much. "
United States
Brandy D.
The price is ￥9,940
￥19,655 total
includes taxes & fees
Mar 8 - Mar 9
Cozy, Bright Home in Historic Downtown
Private kitchen

Apartment in Lexington

‘Edith’ Carriage House Getaway - Hamburg/I-75!
9.0 out of 10, Wonderful, (2 reviews)
"Had a pleasant stay ! Thanks "
United States
brenda s.
The price is ￥7,573
￥21,792 total
includes taxes & fees
Mar 29 - Mar 30
‘Edith’ Carriage House Getaway - Hamburg/I-75!
Terrace/patio

Vacation Home in LEXINGTON

Relaxing Hot Tub | S’mores Fire Pit | Garage
9.2 out of 10, Wonderful, (47 reviews)
"Great place to stay! "
United States
Jeremy S.
The price is ￥14,910
￥39,205 total
includes taxes & fees
Mar 12 - Mar 13
Relaxing Hot Tub | S’mores Fire Pit | Garage
Exterior

Vacation Home in Mount Sterling

1 Bedroom Bourbon House on the Hill
The price is ￥12,496
￥17,255 total
includes taxes & fees
Mar 15 - Mar 16
1 Bedroom Bourbon House on the Hill
Iron/ironing board, WiFi, bed sheets

Vacation Home in Mount Sterling

5 o'clock somewhere in Mt Sterling
The price is ￥13,254
￥18,090 total
includes taxes & fees
Mar 14 - Mar 15
5 o'clock somewhere in Mt Sterling
Outdoor dining

Vacation Home in Lexington

Spacious King Suite | Horses, Fire Pit, Garage
9.8 out of 10, Exceptional, (22 reviews)
"Perfect location for us to get to all of the family activities (golf, horse farm, bourbon tour etc..)Easy check-in & checkoutHost was very responsive Thanks for a great stay"
United States
Tina Y.
The price is ￥12,094
￥42,875 total
includes taxes & fees
Mar 11 - Mar 12
Spacious King Suite | Horses, Fire Pit, Garage
Terrace/patio

Vacation Home in Lexington

Charming Cottage - Near I-75 & Horse Park + Farms
10.0 out of 10, Exceptional, (1 review)
"Everything was perfect for our family. Great communication with host."
United States
Scooby D.
Charming Cottage - Near I-75 & Horse Park + Farms
Property grounds

Vacation Home in Lexington

Midnight Lexington Newly Remodeled Designer Stay
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 ￥39,445
￥86,075 total
includes taxes & fees
Apr 7 - Apr 8
Midnight Lexington Newly Remodeled Designer Stay

Vacation Home in Winchester

The 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 ￥20,590
￥45,311 total
includes taxes & fees
Mar 10 - Mar 11
The Winchester
Dining

Vacation Home in Paris

The Williams House by Mustard Seed Hill - A Cozy Bourbon County Getaway
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 ￥31,398
￥69,301 total
includes taxes & fees
Mar 8 - Mar 9
The Williams House by Mustard Seed Hill - A Cozy Bourbon County Getaway
Exterior

Vacation Home in Winchester

River Relaxation - Calm Riverfront Home in Winchester Kentucky
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 ￥18,689
￥57,650 total
includes taxes & fees
Mar 10 - Mar 11
River Relaxation - Calm Riverfront Home in Winchester Kentucky
Private kitchen

Apartment in Mount Sterling

The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling
The price is ￥20,038
￥25,568 total
includes taxes & fees
Mar 28 - Mar 29
The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling
Exterior detail

Cabin in Bourbon County

Cabin in Kentucky Horse Country
10.0 out of 10, Exceptional, (80 reviews)
"Beautiful property and great host. Paris is a quaint town but plenty of activities to do. "
United Kingdom
Brandon K.
The price is ￥51,279
￥77,156 total
includes taxes & fees
Mar 8 - Mar 9
Cabin in Kentucky Horse Country
Fridge, microwave, oven, stovetop

Vacation Home in Winchester

4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
9.8 out of 10, Exceptional, (7 reviews)
"Very homey place to stay! Nice neighborhood!"
United States
Tim T.
The price is ￥26,034
￥51,312 total
includes taxes & fees
Mar 27 - Mar 28
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
Exterior

Vacation Home in Mount Sterling

Hunting Lodge in the City
The price is ￥13,885
￥18,786 total
includes taxes & fees
Mar 14 - Mar 15
Hunting Lodge in the City
Interior

Vacation Home in Lexington

Fully Furnished 4BR Home in Lexington Short & Mid-Term
The price is ￥45,441
￥102,190 total
includes taxes & fees
Mar 9 - Mar 10
Fully Furnished 4BR Home in Lexington Short & Mid-Term
Exterior

Vacation Home in Millersburg

Helena's Cottage: Romantic, Cozy Getaway with Lavish King Bed, Gas Fireplace
The price is ￥26,034
￥51,410 total
includes taxes & fees
Mar 8 - Mar 9
Helena's Cottage: Romantic, Cozy Getaway with Lavish King Bed, Gas Fireplace
Fridge, microwave, oven, stovetop

Vacation Home in Powell County

Modern Barndo, Hot Tub, Sauna, Fire Pit, 20 min RRG, Rec Room, Pickleball
10.0 out of 10, Exceptional, (10 reviews)
"Great location, tons of things to do, and just about 20-25 min from the gorge."
United States
Veeresh R.
The price is ￥94,441
￥159,805 total
includes taxes & fees
Mar 15 - Mar 16
Modern Barndo, Hot Tub, Sauna, Fire Pit, 20 min RRG, Rec Room, Pickleball
Exterior

Vacation Home in Millersburg

The Parsonage: A Grand 19th Century 4 Bedroom Home
The price is ￥28,400
￥63,915 total
includes taxes & fees
Mar 8 - Mar 9
The Parsonage: A Grand 19th Century 4 Bedroom Home
Fridge, microwave, oven, stovetop

Vacation Home in Millersburg

Historical 1812 Home featuring a Chef's Kitchen, Laundry, and AC
The price is ￥28,400
￥63,915 total
includes taxes & fees
Mar 8 - Mar 9
Historical 1812 Home featuring a Chef's Kitchen, Laundry, and AC
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

Home2 Suites by Hilton Lexington Hamburg

Home2 Suites by Hilton Lexington Hamburg

8/10 Good
"The room was wonderful all but one thing, the bed. Why is it that no matter where we ever stay the beds ar absolutely like sleeping on a dang sheet of plywood?? I will never understand that, oh wait yes I do. No matter where you stay they hope you will not spend anymore time in your room and especially in your bed that you absolutely have to. The bed is the only reason I left a overall 4 star review. In general, please do better with more comfortable beds that aren't like sleeping on a hard floor. My wife and I can't hardly move the next day afterwards. Again I am not singling out just Home 2 Suites but wishing more hotels & motels would do better on the comfort of the beds they provide. Everything else was wonderful, it was our first time staying at a Home 2 Suites. "
Rollin 1-night trip
Posted 8 hours ago
Home2 Suites by Hilton Lexington Hamburg

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?

Spacious King Suite | Horses, Fire Pit, Garage: This vacation home rental outside of North Middletown offers a patio, a garden, 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. You and your friends and family can relax into your vacation with amenities like a selection of games.

What can I see and do in North Middletown?

While you're exploring the area, Winchester Traveling Trail and Bourbon County Park are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Claiborne Farm and Hartfield & Co..

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.