North Middletown Holiday Rentals

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Holiday Rentals in North Middletown

The Bluegrass Diamond Estate

3.0 star property
10.0 out of 10, Exceptional, (4)
"Great for large groups. Beautiful property with amazing views, yet close to town."
The Bluegrass Diamond Estate

Peaceful Mt Sterling Cabin: Deck & Fire Pit!

9.8 out of 10, Exceptional, (11)
"This worked out great for us. The 3rd floor definitely requires someone younger to navigate the spiral staircase. But we loved the creek and the living space to gather and talk at night. "
Peaceful Mt Sterling Cabin: Deck & Fire Pit!

2nd Story Historic Downtown 2BR with Modern Amenities

9.0 out of 10, Wonderful, (12)
"My daughter and I had a wonderful stay. The rental had everything we needed. The location was close to everything."
The price is AU$282
includes taxes & fees
25 Nov - 26 Nov
2nd Story Historic Downtown 2BR with Modern Amenities

Hamburg Retreat: Firepit, Walking Trail, Shopping, Dining, Entertainment & More

9.8 out of 10, Exceptional, (31)
"Great"
Hamburg Retreat: Firepit, Walking Trail, Shopping, Dining, Entertainment & More

Colliver House at Claybank Farm

10.0 out of 10, Exceptional, (44)
"Wonderful quaint farmhouse. Comfortable and cozy. Beautiful surroundings in horse country. Well stocked with everything we needed. Julia was a fabulous host. Attentive and available. "
Colliver House at Claybank Farm

Spacious 3 BR w/ King Suite + Patio Off Interstate

9.8 out of 10, Exceptional, (12)
"Location is good, surrounded by stores and food places. Great host who was very responsive."
The price is AU$416
includes taxes & fees
4 Dec - 5 Dec
Spacious 3 BR w/ King Suite + Patio Off Interstate

Hamburg Haven / Garage /🔥 Pit / 7mi to Rupp / WiFi

9.4 out of 10, Exceptional, (34)
"My daughters and I were stopping for the night on our way into Knoxville and the house was perfect for a girls spa night! Dalton was great and very friendly. One of the cleanest houses we’ve ever stayed in. My only wish was that we stayed for more than one night. Would highly recommend. "
The price is AU$368
includes taxes & fees
1 Dec - 2 Dec
Hamburg Haven / Garage /🔥 Pit / 7mi to Rupp / WiFi

Cozy, Bright Home in Historic Downtown

9.4 out of 10, Exceptional, (13)
"Great downtown location. Cute decor. Could use a few updates but nothing major. Wish we had known the yard & driveway were being rented as it was a little weird having people right outside your windows/doors but we made it work. Most time of the year I'm sure that wouldn't have been any issue. "
The price is AU$206
includes taxes & fees
24 Nov - 25 Nov
Cozy, Bright Home in Historic Downtown

Horse Heaven! Pet friendly farm stay

9.6 out of 10, Exceptional, (14)
"Great location in Horse country!! The house was in need of some attention. The front glass door was falling off and wouldn’t close, the outside entry stairs are in disrepair and need to be redone, and the master bath facet was really leaking. "
Horse Heaven! Pet friendly farm stay

Historic Mt Lebanon, The Governor’s Estate

9.6 out of 10, Exceptional, (18)
"Historical house beautifully restored. Lovingly decorated in a way to make guests feel very comfortable and at home. House sits in middle of beautiful Kentucky countryside."
Historic Mt Lebanon, The Governor’s Estate

Lovely 3 Bdrm Home w/Free Parking Close to I-75!

10.0 out of 10, Exceptional, (15)
"Nice house with everything you need for your stay! Centrally located in the Hamburg area with lots of restaurants and stores to choose from. The host was great and very accommodating."
Lovely 3 Bdrm Home w/Free Parking Close to I-75!

Close to UK, Keeneland and downtown. Rare Country living in the city.

10.0 out of 10, Exceptional, (6)
"Very nice place. Convenient to alot of different things. "
Close to UK, Keeneland and downtown. Rare Country living in the city.

The Cabin at Denali Stud

10.0 out of 10, Exceptional, (11)
"Beautiful fireplace with chopped wood for your use. The ceiling is magnificent and updated throughout. Washer and dryer being in the basement could be a challenge if you are staying for more than a week. Beautiful scenery and so relaxing. "
The Cabin at Denali Stud

Cabin in Kentucky Horse Country

10.0 out of 10, Exceptional, (73)
"Absolutely stunning. A perfect retreat to reset and relax!"
The price is AU$653
includes taxes & fees
24 Nov - 25 Nov
Cabin in Kentucky Horse Country

Welcome Hall 5 bedroom 1880’s home on 55 acres

9.8 out of 10, Exceptional, (27)
"This property is perfect. The kitchen is fully equipped, lots of towels and TP in the bathrooms, and fresh flowers throughout the house was the perfect touch. This beautiful house instantly felt like home . The property owner Patrick was the perfect host. He was attentive and friendly and felt like we have known him forever. Thank you ❤️"
Welcome Hall 5 bedroom 1880’s home on 55 acres

Peaceful Mt Sterling Cabin: Deck & Fire Pit!

3.0 star property
10.0 out of 10, Exceptional, (1)
Peaceful Mt Sterling Cabin: Deck & Fire Pit!

Charming & Inviting Apartment in Historic Downtown Paris, Ky.

9.8 out of 10, Exceptional, (106)
"Exactly as advertised. Host is very helpful. "
Charming & Inviting Apartment in Historic Downtown Paris, Ky.

Large Downtown Artist's Loft, 30 min to Lexington, Horse, Bourbon, R River Gorge

9.6 out of 10, Exceptional, (4)
"It was a great experience, get communication and loved the space!"
Large Downtown Artist's Loft, 30 min to Lexington, Horse, Bourbon, R River Gorge

LanMark Farm Spacious Country Get-Away Ground Floor Suite

10.0 out of 10, Exceptional, (6)
"The property is historic with proper updates that make it a wonderful place to stay. The property owner is very friendly and attentive the swimming pool is refreshing on a hot day and well taken care of making it a great place for everyone. "
LanMark Farm Spacious Country Get-Away Ground Floor Suite

Historic Paris Livery Home of Kentucky's Covered Bridge Tour

9.8 out of 10, Exceptional, (6)
"Host is amazing! This place is simply breathtaking 😍 I have never stayed anywhere so beautiful! She captured the history of this building! We enjoyed our stay and wish we could have stayed longer. You will not regret staying here! Host was easy to get in touch with. She followed up with us upon arrival to make sure our stay was going well! The outdoor fire pit 🔥 patio area 😍🥰😍 This place exceeded our expectations!"
Historic Paris Livery Home of Kentucky's Covered Bridge Tour
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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Other types of properties in North Middletown you may be interested in

Quality Inn Lexington East/Hamburg Area

2.5 star property
7.8 out of 10, Good, (1001)
"The lady working the night shift , when I checked in late that night was super nice and very helpful, very informative, very professional. "
The price is AU$103
includes taxes & fees
23 Dec - 24 Dec
Quality Inn Lexington East/Hamburg Area

GuestHouse Lexington

2.5 star property
8.2 out of 10, Very good, (1080)
"Room was very spacious and clean and it was comfortable to stay in. Breakfast was good and had several options."
The price is AU$120
includes taxes & fees
24 Nov - 25 Nov
GuestHouse Lexington

Home2 Suites by Hilton Lexington Hamburg

3.0 star property
9.4 out of 10, Exceptional, (671)
"A quick stop on our way to Tenn, give the kids a break from driving! Always nice to stay in Lexington. "
The price is AU$174
includes taxes & fees
23 Dec - 24 Dec
Home2 Suites by Hilton Lexington Hamburg
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find a holiday rental in North Middletown?

Yes, there are holiday rentals close to the most popular sights in North Middletown, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that North Middletown has to offer?

The Bluegrass Diamond Estate: This holiday home rental outside of North Middletown offers an indoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 17 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, an arcade/games room and 1 hot tub so that you can immerse yourself in your holiday.

What can I see and do in North Middletown?

While you're exploring the area, Nannine Clay Wallis Arboretum and Lykins Park are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find The Cane Ridge Meeting House and Claiborne Farm.

What are holiday rentals like in North Middletown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in North Middletown. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for family gatherings.