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North Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

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.
The price is ￥15,261
￥20,223 total
includes taxes & fees
Sep 13 - Sep 14
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)
"Clean, unexpected amenities provided in case you forgot something. Ceiling fans in living room and bedroom. Recently renovated. The sweet treats in the fridge upon check in, both local, were a nice touch and paired well with coffee in the morning. Walkable to a nice local bar and grill, downtown area, was a bonus. 5 minutes to I-64. About a half an hour or less to Red River Gorge/ Natural Bridge if you are going hiking. Pet friendly. WiFi. We would definitely stay here again!"
United States
Dan S.
The price is ￥17,619
￥22,822 total
includes taxes & fees
Sep 11 - Sep 12
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.
The price is ￥15,955
￥20,990 total
includes taxes & fees
Sep 11 - Sep 12
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.
The price is ￥50,099
￥75,381 total
includes taxes & fees
Sep 21 - Sep 22
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.
The price is ￥9,844
￥19,465 total
includes taxes & fees
Sep 9 - Sep 10
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.
The price is ￥22,891
￥45,630 total
includes taxes & fees
Sep 10 - Sep 11
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
The price is ￥22,891
￥47,669 total
includes taxes & fees
Sep 20 - Sep 21
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.
The price is ￥6,750
￥20,712 total
includes taxes & fees
Sep 15 - Sep 16
‘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
The price is ￥49,278
￥119,723 total
includes taxes & fees
Sep 9 - Sep 10
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.
The price is ￥43,008
￥83,150 total
includes taxes & fees
Sep 21 - Sep 22
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
The price is ￥18,751
￥24,117 total
includes taxes & fees
Sep 27 - Sep 28
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
The price is ￥36,225
￥64,992 total
includes taxes & fees
Sep 20 - Sep 21
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
The price is ￥50,715
￥92,992 total
includes taxes & fees
Sep 9 - Sep 10
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.
The price is ￥58,598
￥89,672 total
includes taxes & fees
Oct 7 - Oct 8
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.
The price is ￥22,580
￥52,371 total
includes taxes & fees
Sep 15 - Sep 16
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
The price is ￥55,340
￥97,403 total
includes taxes & fees
Sep 9 - Sep 10
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
The price is ￥56,881
￥99,268 total
includes taxes & fees
Sep 9 - Sep 10
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.
The price is ￥44,395
￥98,406 total
includes taxes & fees
Sep 9 - Sep 10
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.
The price is ￥20,089
￥59,243 total
includes taxes & fees
Sep 14 - Sep 15
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.
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

Best Western Winchester Hotel

Best Western Winchester Hotel

10/10 Excellent
"Front desk staff were very nice and helpful! Breakfast was small but well done. Rooms were clean. Could use some updating but this did not hinder our stay. Only negative I had was the pool was out of order and we were not informed at booking. Great place."
Lydia 3-night trip
Posted 1 hour ago
Best Western Winchester Hotel

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?

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.