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.

Bourbon Trail Estate | 3 Epic Acres | 7 Bed 6 Bath

Welcome to your ultimate Louisville getaway! 🏡 This private 5BR retreat blends space, comfort, and style with unbeatable access to the Bourbon Trail, dining, and attractions—perfect for families or groups. ✨ Spacious 5BR, 5.5BA Retreat – 7 beds (5 Kings) 🛏️ 🍳 3 Full Kitchens + Bar 🎬 Entertainment Room w/ Media System – Perfect for Game Night 🎮 🌳 Private Backyard for Dining & Relaxing 🥃 Quiet setting just minutes from Bourbon Trail, Shopping & Top Attractions A serenity-meets-convenienc

Home near the Highways

Comfortable, clean home in a quiet neighborhood Garage and driveway parking 3 Kings, 2 Queens, 2 Full beds, 2 Futons, 1 Loveseat Sleeper Sofa, 1 Couch Individual coffee makers in rooms with complementary coffee Peaceful front porch. Back and patio with gas & charcoal grills and green view Pet Friendly. Scroll down to "Other Things to Note" for more info. 2.5 miles to I-265. 3 miles to I-64. 20-30 minutes to most places in Louisville. 1 mi to a fuel, groceries, restaurants & banking

Unique Serenity - Entire Home On Private 3-Acres

A perfect place for family and friends to spend time together. This unique home is spacious and sits on 3-acres well-maintained property. You can enjoy all the local shops, restaurants, parks, and golf courses while staying in what feels like a secluded country-side setting. 4br, 4ba, large kitchen and dining area with granites throughout. Large covered porch for outdoor enjoyment. 4 smart tv's, high speed wifi, washer/dryer, and iron are provided. Sleeps 12+. RVs and trailers welcome.

Safe, comfortable, convenient, hot tub, fire pit!

Forget your worries in this spacious and serene space. Located in the East-end of Louisville and is conveniently located near a vast array of restaurants, shops, and entertainment. This Property has two king bedrooms, one queen bedroom, one queen sleeper sofa, two bunk beds. It has two full baths, two living room areas, pool table, dart board, hot tub that holds 7 people and a fire pit. There are several acres with an abundance of rare trees, bushes, and flowers with a swing in the front.

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.

"Call Me Old-Fashioned"in Derby & Bourbon Country!

Welcome to "Call Me Old-Fashioned" - a unique spin on Bourbon w/ a mix of new & vintage amenities! Located in a QUIET & SAFE neighborhood, this family-friendly home is located close to Downtown Louisville & Churchill Downs (18 min), Expo Center & airport (15 min). Bardstown, the Bourbon capitol, is 35 min away. We are also 5 min from Parklands @ Floyds Fork park system - home to 60 miles of hiking, biking & paddling trails & a big playground. Come make yourself at home in our cozy KY home!

Spacious Louisville getaway with private backyard!

Welcome to your Louisville retreat, designed with large groups in mind. Set in a quiet, residential neighborhood, this spacious home offers a calm, serene atmosphere ideal for unwinding together. With 5 comfortable bedrooms and multiple living areas, it easily accommodates up to 16 guests. Enjoy a fully equipped kitchen, a cozy fireplace, and a private backyard perfect for relaxed mornings and peaceful evenings—ideal for families and group getaways seeking comfort and quiet.

Red Bridge Retreat

Red Bridge Retreat is your perfect Christmas getaway! Set on 5 serene acres just outside Louisville, you’re only 30 minutes from major holiday events. Elegant, stylish décor throughout. This 4-bed, 3-bath private home features a kitchen deck with a Blackstone & gas grill, a covered patio with HOT TUB, a covered fire-pit area, a fully equipped kitchen, a game room with bumper pool & Pac-Man, and a tree-lined drive. It even includes a bourbon-themed lounge to unwind and relax.

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.

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!

Charming Bungalow on 1.5 Acres in Amazing Location

Peaceful. Private. Clean. Comfortable. Convenient. Hummingbird is a charming updated bungalow in one of Louisville's most coveted neighborhoods. Nestled on 1.5 acres of a historic street, you'll enjoy a park-like setting teeming with wildlife. Private, yet offering easy access to shopping, dining, entertainment, and major highways, this hidden gem is sure to please. Whether here work, fun, or both, you’ll love your time at Hummingbird.