North Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for North Middletown vacation rentals

A living room with a beige sofa, a large plant, a wall mural, a door with a star decoration, and a black entertainment unit.

1. Cozy, Bright Home in Historic Downtown

Cozy, Bright Home in Historic Downtown
Mount Sterling
8.4 out of 10, Very good, (25 reviews)
"This is definitely an older home, but it was clean and comfortable and the Dolly memorabilia is amazing!"
United States
Glenda
The price is CA $90
CA $165 total
includes taxes & fees
Nov 16 - Nov 17
Cozy, Bright Home in Historic Downtown
Interior

2. 5 o'clock somewhere in Mt Sterling

5 o'clock somewhere in Mt Sterling
Mount Sterling
9.0 out of 10, Wonderful, (4 reviews)
"A good stay in a friendly area."
United States
Trey S.
The price is CA $148
CA $182 total
includes taxes & fees
Nov 23 - Nov 24
5 o'clock somewhere in Mt Sterling
Exterior

3. Hunting Lodge in the City

Hunting Lodge in the City
Mount Sterling
The price is CA $154
CA $189 total
includes taxes & fees
Nov 16 - Nov 17
Hunting Lodge in the City
A kitchen with a microwave, coffee maker, and tea storage.

4. 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, (3 reviews)
"Very easy check in and nice location"
United States
Robert G.
The price is CA $181
CA $219 total
includes taxes & fees
Dec 1 - Dec 2
The PawPlex a Cozy 1-bedroom apartment in marvelous Mount Sterling
A two-story house with a porch and a front yard.

5. Charming Victorian Apartment | Downtown Winchester

Charming Victorian Apartment | Downtown Winchester
Winchester
The price is CA $83
CA $525 total
includes taxes & fees
Nov 16 - Nov 17
Charming Victorian Apartment | Downtown Winchester
A wooden deck with wicker chairs and a small table.

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

‘Edith’ Carriage House Getaway - Hamburg/I-75!
Lexington
8.4 out of 10, Very good, (10 reviews)
"A great one night stay! Plenty of room. Nice kitchen area and outside deck."
United States
Kevin P.
The price is CA $70
CA $200 total
includes taxes & fees
Dec 9 - Dec 10
‘Edith’ Carriage House Getaway - Hamburg/I-75!
A rural road curving through a green landscape with a wooden fence, a stone wall, and a small building in the distance.

7. Historical 4-bedroom farmhouse in serene Sharpsburg with AC.

Historical 4-bedroom farmhouse in serene Sharpsburg with AC.
Sharpsburg
9.6 out of 10, Exceptional, (9 reviews)
"We had a great time with the family."
United States
Garrett W.
The price is CA $321
CA $590 total
includes taxes & fees
Nov 16 - Nov 17
Historical 4-bedroom farmhouse in serene Sharpsburg with AC.
A bedroom with a bed, nightstands, and a dresser.

8. 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
9.6 out of 10, Exceptional, (14 reviews)
"Very homey place to stay! Nice neighborhood!"
United States
Tim T.
The price is CA $193
CA $403 total
includes taxes & fees
Nov 16 - Nov 17
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
A two-story house with a covered porch, a brick exterior, and a small garden area with shrubs.

9. 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 CA $193
CA $403 total
includes taxes & fees
Nov 16 - Nov 17
The Winchester
A red Adirondack chair by a river in a wooded area.

10. Cabin in Kentucky Horse Country

Cabin in Kentucky Horse Country
Bourbon County
10.0 out of 10, Exceptional, (82 reviews)
"Beautiful cabin with wonderful views in a peaceful setting"
United Kingdom
Siobann S.
The price is CA $464
CA $663 total
includes taxes & fees
Nov 16 - Nov 17
Cabin in Kentucky Horse Country
A living room with a horse sculpture centerpiece, blue sofas, a chandelier, and wall-mounted decor.

11. 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 CA $195
CA $410 total
includes taxes & fees
Nov 18 - Nov 19
The Parsonage of Paris
A doorway leading to a room with a patterned chair and a painting on the wall.

12. Charming Apartment in the Heart of Carlisle

Charming Apartment in the Heart of Carlisle
Carlisle
10.0 out of 10, Exceptional, (1 review)
"This is the cutest place to stay in a very welcoming community. Loved how the town was all decorated for fall and Halloween."
United States
Stephanie D.
The price is CA $243
CA $388 total
includes taxes & fees
Nov 16 - Nov 17
Charming Apartment in the Heart of Carlisle
An outdoor patio area with a fire pit, wicker furniture, and a pool.

13. Bluegrass Bourbon Retreat/Pool/ Downtown Paris

Bluegrass Bourbon Retreat/Pool/ Downtown Paris
Paris
The price is CA $349
CA $970 total
includes taxes & fees
Dec 1 - Dec 2
Bluegrass Bourbon Retreat/Pool/ Downtown Paris
A bedroom with a bed, a chair, a mirror, and a wardrobe.

14. 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)
"Awesome house and perfect for our family. Only issue was the master bath has a second door into the laundry room that doesn’t close and latch. So not the best for privacy. But loved the stay!"
United States
R T.
The price is CA $285
CA $597 total
includes taxes & fees
Nov 16 - Nov 17
The Williams House by Mustard Seed Hill - A Cozy Bourbon County Getaway
A house with a blue door, two windows with shutters, and a porch with a white railing.

15. 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 CA $264
CA $487 total
includes taxes & fees
Nov 16 - Nov 17
Helena's Cottage: Romantic, Cozy Getaway with Lavish King Bed, Gas Fireplace
A two-story building with a white front door, two windows with shutters, and a small porch with a railing.

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

Historical 1812 Home featuring a Chef's Kitchen, Laundry, and AC
Millersburg
10.0 out of 10, Exceptional, (1 review)
"This property is perfect for families traveling together. Each bedroom has its own bathroom and plenty of room for everyone to relax. The kitchen is perfect and the back porch makes a great place to have your coffee in the morning or in the evening. It’s only 20 minutes from Cynthia Anna and less than 10 minutes from Paris, so if you were looking for a great place to stay look no further! We had an issue with one of the beds and they took care of it within a few hours"
United States
Michelle
The price is CA $412
CA $749 total
includes taxes & fees
Nov 23 - Nov 24
Historical 1812 Home featuring a Chef's Kitchen, Laundry, and AC
A staircase with a brick wall and a painted sheep mural.

17. Marvelous 3-bedroom second floor apartment in Carlisle with lots of history

Marvelous 3-bedroom second floor apartment in Carlisle with lots of history
Carlisle
10.0 out of 10, Exceptional, (1 review)
"Location was perfect for what we needed. It was exceptionally clean which is much appreciated."
United States
caseycycling
The price is CA $243
CA $399 total
includes taxes & fees
Nov 16 - Nov 17
Marvelous 3-bedroom second floor apartment in Carlisle with lots of history
A two-story house with a brick facade, a white garage door, and a small front porch.

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

Relaxing Hot Tub | S’mores Fire Pit | Garage
LEXINGTON
9.4 out of 10, Exceptional, (55 reviews)
"Great stay will think of this place if we ever go back to lexington"
United States
Stephanie S.
The price is CA $165
CA $428 total
includes taxes & fees
Nov 18 - Nov 19
Relaxing Hot Tub | S’mores Fire Pit | Garage
A two-story house with a beige exterior, numbered 1112, featuring a front porch with two wicker chairs and two wall-mounted lanterns.

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

The Neal House: Charming & Historic 3 Bedroom House
Millersburg
The price is CA $355
CA $680 total
includes taxes & fees
Nov 16 - Nov 17
The Neal House: Charming & Historic 3 Bedroom House
A green exterior with a pink door, two wall-mounted lights, and a wicker chair.

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

The Parsonage: A Grand 19th Century 4 Bedroom Home
Millersburg
The price is CA $398
CA $732 total
includes taxes & fees
Nov 16 - Nov 17
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

A Holiday Inn Express building with a covered entrance, stone pillars, and potted plants.
Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
Winchester

8/10 Good

Good place to stay
Canada
martin
Reviewed April 30, 2025
Holiday Inn Express Lexington East - Winchester by IHG

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A North Middletown vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of North Middletown vacation rentals we have selected for you start as low as CA $69 per night. Entering your travel dates in the search wizard 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, Lake Carnico and College Park 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.