Vacation rentals in Middletown

Garden House, a private getaway

Welcome to "The Garden House" a serene retreat nestled on 9 acres in Crestwood. This charming home offers a tranquil escape just 20 minutes from downtown Louisville. This home is a 4-bedroom sanctuary, meticulously renovated to offer modern comforts. Guests can enjoy premium amenities including solar power, Tempurpedic mattresses, and soft bedding for a great night's sleep. Whether you are planning a wedding, exploring the Bourbon Trail, or seeking a getaway, it promises to be a memorable stay.

Location · Family · Kitchen

Entire House in Middletown - Trailers/RVs access

Make some memories at this unique and family-friendly place. Enjoy your morning coffee or spend your evening with family and friends on the rear deck overlooking the peaceful, spacious 2-acres, park-like view. The property is conveniently located close to everything including restaurants, supermarkets, amusement park, indoor malls, outlet mall. The home features 3 bedrooms, 2.5 baths, with granite countertops throughout. Enjoy your indoor space with wifi, tv's. Sleeps 6 to 8. Can park RV's.

Family · Location · Comfort

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.

Location · Value · Getting around

Breakfast At Tiffany's

This private detached in-law suite with driveway access will make you feel like your staying with family. An open plan living area let's you relax and feel at home while enjoying a modern kitchen, spacious shower, and cozy bedroom with a vaulted ceiling and exposed brick. We're located within walking distance of Charlie Vettiner Golf Course and Park so if you have an early tee time, a long game, or come into town for a Pickle Ball tournament, you're welcome to stay with family in our suite.

Value · Family · Check-in

Historic Cabin by Bourbon Trail

Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

Location · Value · Parking

Perfect for Work or Play, Close to Everything!

Whether you're here for work or play, our Airbnb offers the perfect base for your Kentucky adventures! Welcome to your home away from home! Nestled in the quiet suburbs, our modern & spacious retreat offers the perfect blend of comfort & convenience. Whether you’re here to explore the famous Bourbon Trail, work remotely, or simply unwind, you’ll find everything you need right here! Close to shopping, dining, entertainment, major highways, top bourbon distilleries and downtown Louisville.

Location · Family · Check-in

The Cottage @ Mellwood

BRAND NEW CONSTRUCTION! This cozy cliff side cottage offers serenity in the city with amazing outdoor spaces and beautiful view of the downtown skyline. It is centrally located, minutes away from downtown Louisville & NULU. This property is especially unique as it is steps away from Mellwood Arts Center; home to events, art studios, shops, cafes, and brewery. This location is ideal for any wedding party, bourbon tours, festivals, fireworks show or any other reason to visit the Derby city!

Location · Family · Check-in

Briar Creek Cottage

Welcome to this cozy 2-bed, 2-bath cottage, just 25 minutes from the Louisville Airport & conveniently close to the Kentucky Bourbon Trail. Recently renovated, this cottage is nestled in a peacefully wooded lot with modern amenities. The primary suite includes a queen bed, an en suite bathroom, and an optional pack-n-play. The second bedroom also features a queen bed and adjacent bath. Perfect for a tranquil getaway or exploring the Kentucky Bourbon Trail. Book now for a charming retreat!

Family · Value · TV

This old Kentucky home - Middletown/Derby/Bourbon

Please note this listing is for the lower level only not the entire house. However, you will feel like it's your home away from home. You will have use of the entire lower lever, which is a spacious 1600 sf (accessed via private/walk out entrance). 3 BR/2 full Bath. Main floor of home is owner occupied, via private/separate entrance. While the unit sleeps 6 comfortably, after 4 guests the rate increases by $50 per person per night. 2 parking spaces allotted LIC-STL-25-00086

Value · Location · Parking

The gaited guesthouse

🌿 Relax in our charming guest house tucked away on a beautiful family owned horse farm. The Garland Reid Farm was established by the same family in 1980 and is set back on a quiet street yet is minutes to shopping. Overlooking rolling fields and horses, it’s the perfect retreat for up to three guests looking for peace, comfort, and the serenity of farm life. The guest house is attached to the main house by a deck, hosts will assure you have total privacy.

Family · Location · Bathroom

SuperHost ~ Beautiful NEW Condo Near Louisville!

🎯 Prime Location in Douglass Hills, KY 🏡 Minutes from Louisville – Perfect for a peaceful stay with quick access to city attractions 🐎 Close to Churchill Downs & the Derby Museum – A must for horse racing fans and history lovers! 🛍 Near Oxmoor Center & Mall St. Matthews – shopping, dining, and entertainment. 🚗 Easy Access to I-64 & I-264 – Convenient travel to Louisville, the airport, and local parks. 🛏 Book now and enjoy your Kentucky getaway!

Location · Family · Indoor spaces

My Old Kentucky Dome

An elevated camping “glamping” experience. This brand-new one of a kind geodesic dome is located on a private road that leads you to an overlook featuring one of the most beautiful countryside views in Kentucky. While this getaway experience is nestled deep in the woods, it is also a close drive to all the conveniences you can imagine. This is an off the grid outdoor experience with a ½ mile gravel road including a steep hill. AWD or 4WD advised.

Value · Location · Grill