Vacation rentals in Middletown

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Top-rated vacation rentals in Middletown

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Guest favorite

Cabin in Louisville

4.95 out of 5 average rating, 304 reviews

Captain's Cabin:Historic Romantic by Bourbon Trail

Your own log cabin on a wooded hillside overlooking a private lake with gourmet breakfast served to your door (on weekends)! It's been the location for Lifetime and Hallmark movies! Period furnishings and modern conveniences make this an unforgettable retreat. A massive stone fireplace creates a quiet ambiance. Watch wildlife from back porch swings. Comfy bed, luxury sheets, high-speed internet, bluetooth stereo and special touches make your stay magical! Ask for Cooking With Bourbon Experience

Jan 11 – 18

R5,001 ZAR per night

Guest favorite

Guest suite in Jeffersonville

4.93 out of 5 average rating, 152 reviews

RIView 103. Modern Waterfront Suite Kentucky Derby

Guests can enjoy scenic views of the mighty Ohio River from any room in their private suite. Catch a beautiful sunrise or relax while sitting on the porch watching the boats and barges cruise the river. Close drive to interstate to get you to downtown Louisville to enjoy a dinner, museum, basketball game or concert in the KFC YUM Center and the world famous Churchill Downs! 1 mile away from River Ridge. We do offer a Tesla only charger or you can bring your own standard attachment for a charge.

Mar 15 – 22

R2,860 ZAR per night

Guest favorite

Guest suite in Louisville

4.93 out of 5 average rating, 211 reviews

Hide away close to everything

Recently remodeled in law suite. We just upgraded the bed to a queen size. Very private, detached garage getaway. A cozy sitting area 60" CableTV with HBO SHOWTIME and STARZ. Wet bar with fridge, ice maker, coffee maker, microwave, hot plate, dishes and some cookware. Private bath has shower and a walk in closet. This private apt. is above the garage. Outside has fenced in yard for your furry friend, outdoor fire pit and sitting area. Close to the interstate and minutes from downtown.

Jun 15 – 22

R1,355 ZAR per night

Guest favorite

Guest suite in Louisville

4.97 out of 5 average rating, 119 reviews

Derby City Hideaway

Whiskey Hollow offers you a unique stay with our Bourbon-themed space. Your stay in Kentucky is sure to be memorable and cozy. Our newly renovated space offers a full kitchen, cozy living area, bedroom and full bath with a private patio. Local attractions include Churchill Downs, home of the Kentucky Derby, Kentucky Derby Museum. Louisville Slugger Museum, Kentucky Bourbon Trail, local city eats, 4th Street Live, horse farms, hiking, waterfalls, parks, shopping, local arts, and much more!

Feb 17 – 24

R2,021 ZAR per night

Guest favorite

Guest suite in Louisville

4.98 out of 5 average rating, 179 reviews

Spacious Lower-Level in Quiet Neighborhood

This is a spacious, walk-out lower level with a private entrance. Our quiet neighborhood is 1 1/2 miles from I-265, which means easy access to Louisville or beyond the city to bourbon country. It has a large living area and a fully equipped kitchen. Adventure lovers will like being 5 miles from The Parklands. Downtown Louisville is 20 minutes away. The space has 1 queen bed, 1 double bed, and twin bunk beds. It sleeps 5-6 comfortably. We live upstairs so we are available if needed.

Jun 18 – 25

R2,634 ZAR per night

Guest favorite

Tiny home in La Grange

4.98 out of 5 average rating, 161 reviews

Brakeman's Cottage

"All Aboard the Brakeman's Cottage! Experience the charm of this tiny house listed on the National Register of Historic Buildings in LaGrange, Kentucky. Nestled just feet from the train tracks in the heart of downtown, it offers a unique experience. Situated across from the train observation tower and within walking distance of the best restaurants and quaint shops, our newly remodeled property features private off-street parking. Step into history with modern comforts at Brakeman's

Dec 8 – 15

R1,867 ZAR per night

Guest favorite

Home in Louisville

4.85 out of 5 average rating, 166 reviews

Private EAST END gem, minutes from everything!

Cozy, East End cottage just minutes from Top Golf, shopping malls, restaurants, entertainment, and other amenities. Easy access to the expressway. Home is well appointed with granite countertops, stainless appliances, hardwood floors, and more. A seasonal creek across from the house can be heard giving the impression of a cabin in the woods with privacy and seclusion, with the convenience of city living at your fingertips. There is also a beautiful park steps away from the house.

Jul 14 – 21

R1,511 ZAR per night

Guest favorite

Guest suite in Prospect

4.97 out of 5 average rating, 169 reviews

Private Prospect Flat

Two bedroom apartment located on picturesque Covered Bridge Road in Prospect, KY. There is a separate entrance with plenty of parking. Beautiful views of Kentucky landscape from every window. Our property is four acres with a meandering stream, forest, and fields. There is a fully stocked kitchen including a dishwasher. The main bedroom includes a work space area and two closets. Feel free to grab a few eggs for breakfast if there are eggs in the nesting boxes.

May 31 – Jun 7

R2,684 ZAR per night

Guest favorite

Guesthouse in Louisville

4.95 out of 5 average rating, 220 reviews

Comfortable-relaxed space to find your inspiration

Located in the Germantown neighborhood of Louisville, this peaceful efficiency apartment in a traditional "shotgun" home, built in the 1890s, is within 10 minutes of nearly all of Louisville’s airport traveler’s attractions. Guests enjoy great sleep on top bedding and attention to detail. Sit on the front porch and let time slip by or spend the evening with a relaxing drink or meal in one of the neighborhood’s hip local eateries and bars. Plan your next journey.

Oct 23 – 30

R1,258 ZAR per night

Guest favorite

Guesthouse in Louisville

4.97 out of 5 average rating, 112 reviews

The City Cottage…quiet, peaceful, and convenient!

A quaint, cozy, and private space close to everything Louisville has to offer. Located on the Northeast side of Louisville, The City Cottage is near the highways for quick access to destinations in and around Louisville. This newly completed space is fresh, clean and created for guests in mind. Are you a couple traveling or a business person wanting more room and comfort than a typical hotel? The City Cottage is for you! (Three night minimum during Derby time.)

Jun 29 – Jul 6

R2,959 ZAR per night

Guest favorite

Home in Louisville

4.95 out of 5 average rating, 111 reviews

HOUSE ON HERRICK

Fully renovated home in the heart of Historic Middletown. Hardwood and tile floors throughout. Queen size memory foam mattresses in both bedrooms and a full-size blowup mattress can be used in the living room if needed. 3 blocks from Main Street where you will find restaurants, shopping, and antiques! 15 minutes from Churchill Downs! Less than 1 mile to Interstate 64 with a quick Uber ride to downtown, Crescent Hill, and the Highlands.

Sep 11 – 18

R2,316 ZAR per night

Guest favorite

Guest suite in Louisville

4.95 out of 5 average rating, 289 reviews

Highlands Lower Level Studio Guest Suite

Private, well-lit, entrance is in rear of home. The space is approx. 600sq. ft. There is a gas fireplace, 42" HD TV w/Netflix & Amazon Prime. Kitchen has Keurig coffee maker, convection oven, inferred glass top burner, microwave, refrigerator/freezer w/ice, washer/dryer& a large marble shower, with heated floors in the shower room. Also space equipped w/ Medify air purifier w/H13 true Hepa medical grade filter.

Jan 4 – 11

R1,601 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Middletown vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Middletown's top sights

Kroger13 locals recommend

Havana Rumba Middletown32 locals recommend

Southeast Christian Church4 locals recommend

Blind Squirrel10 locals recommend

House of Boom Extreme Air Sports4 locals recommend

Joella's Hot Chicken4 locals recommend

Other great vacation rentals in Middletown

Guest favorite

Apartment in Louisville

4.95 out of 5 average rating, 355 reviews

Sunny Clifton Loft

Jun 1 – 8

R1,979 ZAR per night

Guest favorite

Apartment in Louisville

4.94 out of 5 average rating, 231 reviews

Chic, Luxurious Carriage House in Ideal Location

Dec 11 – 18

R2,750 ZAR per night

Guest favorite

Cottage in Shelbyville

4.92 out of 5 average rating, 166 reviews

Cozy Cottage on Firefly Farm

Dec 11 – 18

R1,639 ZAR per night

Guest favorite

Guest suite in Louisville

4.97 out of 5 average rating, 106 reviews

Action City! Extravaganza at Bardstown Rd!

Jun 19 – 26

R1,670 ZAR per night

Guest favorite

Guesthouse in Louisville

4.91 out of 5 average rating, 452 reviews

Cute Carriage House off Frankfort Avenue

Aug 24 – 31

R1,227 ZAR per night

Guest favorite

Townhouse in Louisville

4.95 out of 5 average rating, 214 reviews

Louisville Charm: Walk to it All! Central & Quaint

Jun 15 – 22

R2,370 ZAR per night

Guest favorite

Guest suite in Louisville

4.97 out of 5 average rating, 31 reviews

Middletown Private Guest House

Jun 16 – 23

R1,750 ZAR per night

Guest favorite

Guesthouse in Prospect

5.0 out of 5 average rating, 30 reviews

Prospect Guest House

Jan 8 – 15

R2,261 ZAR per night

Show all

Quick stats about vacation rentals in Middletown

Total rentals
50 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
970 reviews
Nightly prices starting at
R571 ZAR before taxes and fees

Frequently Asked Questions

Do house rentals in Middletown have air conditioning?
Absolutely! We offer over 40 house rentals with air conditioning in Middletown. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Middletown?
Four-legged friends are welcome in Middletown. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Middletown?
Yes! Work meets play with ease at over 20 vacation rentals in Middletown featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there family-friendly vacation rentals in Middletown?
Middletown has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Middletown have a kitchen?
Absolutely! We offer over 40 house rentals with a kitchen in Middletown. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Middletown?
Experience the best of Middletown with our house rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Middletown have wifi?
Absolutely! We offer over 40 house rentals with wifi in Middletown. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Middletown have free parking?
Absolutely! We offer over 40 house rentals with free parking in Middletown. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Middletown

Top-rated vacation rentals in Middletown

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Middletown vacation rentals

Stay near Middletown's top sights

Other great vacation rentals in Middletown

Apartment in Louisville

Apartment in Louisville

Cottage in Shelbyville

Guest suite in Louisville

Guesthouse in Louisville

Townhouse in Louisville

Guest suite in Louisville

Guesthouse in Prospect

Quick stats about vacation rentals in Middletown

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Middletown have air conditioning?

Are there pet-friendly vacation rentals in Middletown?

Are there vacation rentals with a dedicated workspace in Middletown?

Are there family-friendly vacation rentals in Middletown?

Do house rentals in Middletown have a kitchen?

How much does it cost to stay in house rentals in Middletown?

Do house rentals in Middletown have wifi?

Do house rentals in Middletown have free parking?

Destinations to explore