New Middletown Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
18 Jul - 19 Jul
Tomorrow
19 Jul - 20 Jul
This weekend
18 Jul - 20 Jul
Next weekend
25 Jul - 27 Jul

Holiday Rentals in New Middletown

Putt Putt House by Louisville Walking Bridge
Private kitchen

Putt Putt House by Louisville Walking Bridge

2.0 star property
10.0 out of 10, Exceptional, (4)
"Property was clean, well lit and very pretty. Location was near food, drink and activities, parking very accessible. Owner communicated promptly too. "
The price is NZ$498
includes taxes & fees
21 July - 22 July
Putt Putt House by Louisville Walking Bridge
Bourbon Trail Spacious Backyard NEW HotTub Grill!
Outdoor spa tub

Bourbon Trail Spacious Backyard NEW HotTub Grill!

2.0 star property
10.0 out of 10, Exceptional, (1)
"Excellent walking to different little shops. Super decorated inside and out. Loved the hot tub. Would stay again! "
The price is NZ$503
includes taxes & fees
31 July - 1 Aug
Bourbon Trail Spacious Backyard NEW HotTub Grill!
Steps to Restaurants, Nightlife, Shops~PacMan/King Bed~Bardstown Rd/Highlands
Property grounds

Steps to Restaurants, Nightlife, Shops~PacMan/King Bed~Bardstown Rd/Highlands

10.0 out of 10, Exceptional, (6)
"From the moment we arrived we knew this place was perfect for our crew's Louder than Life experience. Upon entering, the place was clearly very well taken care of and offered a premium feel. The location is a huge plus. Bardstown road has so much to offer, we stayed for 6 days and we feel like we barely scratched the surface. Everywhere we went had a great atmosphere and even better food. My crew was joking that this place was so perfect that we need to book it in advance every year. We just...
The price is NZ$491
includes taxes & fees
28 July - 29 July
Steps to Restaurants, Nightlife, Shops~PacMan/King Bed~Bardstown Rd/Highlands
Cozy Retreat Near Downtown Lou and Attractions
Living area

Cozy Retreat Near Downtown Lou and Attractions

Cozy Retreat Near Downtown Lou and Attractions
DerbyCity Getaway | Hot Tub | Near Churchill Downs
Terrace/patio

DerbyCity Getaway | Hot Tub | Near Churchill Downs

8.4 out of 10, Very good, (6)
"Loved the backyard "
The price is NZ$362
includes taxes & fees
6 Aug - 7 Aug
DerbyCity Getaway | Hot Tub | Near Churchill Downs
7Mi Louisville Pet-Friendly Home
Fridge, microwave, oven, stovetop

7Mi Louisville Pet-Friendly Home

7Mi Louisville Pet-Friendly Home
8 Mi Louisville New Albany Home
Fridge, microwave, oven, stovetop

8 Mi Louisville New Albany Home

The price is NZ$519
includes taxes & fees
21 July - 22 July
8 Mi Louisville New Albany Home
Cozy Home | Just Steps Away from Churchill Downs!
Fridge, microwave, oven, stovetop

Cozy Home | Just Steps Away from Churchill Downs!

2.0 star property
7.4 out of 10, Good, (3)
"Very nice "
The price is NZ$566
includes taxes & fees
18 Aug - 19 Aug
Cozy Home | Just Steps Away from Churchill Downs!
NEW Hot Tub, Expo, King Beds, Downtown, Churchill
Terrace/patio

NEW Hot Tub, Expo, King Beds, Downtown, Churchill

9.8 out of 10, Exceptional, (74)
"Great property! Perfect for the five couples! House was very cute and relaxing! Plenty of space for all 10 of us!"
The price is NZ$1,169
includes taxes & fees
30 July - 31 July
NEW Hot Tub, Expo, King Beds, Downtown, Churchill
Cozy Downtown Stay w/ Private Backyard & Parking
Fridge, microwave, oven, stovetop

Cozy Downtown Stay w/ Private Backyard & Parking

8.0 out of 10, Very good, (1)
"Overall, it was not a bad unit but could be cleaned up a little bit and add some air fresheners."
The price is NZ$362
includes taxes & fees
21 July - 22 July
Cozy Downtown Stay w/ Private Backyard & Parking
NuLu Private Home|Backyard|Parking
Fridge, microwave, stovetop, dishwasher

NuLu Private Home|Backyard|Parking

8.8 out of 10, Excellent, (19)
"I traveled for work. This house was located near downtown and close to everything. The house was very clean and comfortable. "
The price is NZ$383
includes taxes & fees
20 July - 21 July
NuLu Private Home|Backyard|Parking
Cozy, historic, pet-friendly home!
Microwave, oven, stovetop, dishwasher

Cozy, historic, pet-friendly home!

9.8 out of 10, Exceptional, (25)
The price is NZ$591
includes taxes & fees
23 July - 24 July
Cozy, historic, pet-friendly home!
New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!
Fridge, microwave, oven, stovetop

New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!

9.8 out of 10, Exceptional, (18)
"Thia was a great place to stay during our visit to the National Farm Machinery Show."
The price is NZ$349
includes taxes & fees
20 July - 21 July
New! Walk to the Kentucky Derby, U of L Football, and Jim Patterson Stadium!
Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.
Fridge, microwave, oven, stovetop

Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.

10.0 out of 10, Exceptional, (23)
"We stopped for one night traveling through. The place was clean, easy to find, and close to a charming downtown. It was also close to many Louisville attractions. Rebecca was very quick to respond and was very communicative. "
The price is NZ$365
includes taxes & fees
12 Aug - 13 Aug
Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.
Stylish Home in Historic District Near Riverwalk
TV

Stylish Home in Historic District Near Riverwalk

The price is NZ$496
includes taxes & fees
31 July - 1 Aug
Stylish Home in Historic District Near Riverwalk
Stylish Retreat: Walkable to Bars & Restaurants!
Dining

Stylish Retreat: Walkable to Bars & Restaurants!

Stylish Retreat: Walkable to Bars & Restaurants!
Walk to Churchill & Cardinal Stadium Near SDE!
Exterior

Walk to Churchill & Cardinal Stadium Near SDE!

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property had 3 nice size bedrooms and 1-1/2 baths with a modern kitchen and nice layout. I appreciated the quiet neighborhood and off road parking."
The price is NZ$457
includes taxes & fees
30 July - 31 July
Walk to Churchill & Cardinal Stadium Near SDE!
The Chestnut - Nulu
Terrace/patio

The Chestnut - Nulu

2.0 star property
9.8 out of 10, Exceptional, (16)
"This is an awesome place to stay, felt like home. The beds are really comfortable. We made a great choice in choosing VRBO instead of hotel!!"
The price is NZ$325
includes taxes & fees
21 July - 22 July
The Chestnut - Nulu
The Adelyn, where comfort meets convenience
Exterior

The Adelyn, where comfort meets convenience

10.0 out of 10, Exceptional, (2)
"Convenient to all Louisville destinations and downtown Jeffersonville "
The price is NZ$534
includes taxes & fees
20 July - 21 July
The Adelyn, where comfort meets convenience
"Oak & Barrel" #1 LOCATION in Louisville. Bourbon & Derby theme. Pets welcome.
Interior

"Oak & Barrel" #1 LOCATION in Louisville. Bourbon & Derby theme. Pets welcome.

10.0 out of 10, Exceptional, (7)
"We had a great visit in Louisville staying here! Plenty of room and nicely decorated house."
The price is NZ$632
includes taxes & fees
30 July - 31 July
"Oak & Barrel" #1 LOCATION in Louisville. Bourbon & Derby theme. Pets welcome.
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

Can I find a holiday rental in New Middletown?

Yes, there are holiday rentals close to the most popular sights in New 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 New Middletown has to offer?

Newly renovated 4BR CozySuites: This holiday home rental outside of New Middletown offers a garden, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in New Middletown?

Explore the area and family-friendly sights such as Kentucky Derby Museum, or get out into nature at a spot like Squire Boone Caverns. Corydon Capitol State Historic Site and Horseshoe Southern Indiana Casino are a couple of places you'll find in the wider area.

What are holiday rentals like in New Middletown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in New Middletown. Holiday rentals feature extras like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for family trips.