Holiday rentals in Middletown

4.92 out of 5 average rating, 13 reviews

Home in Jeffersontown

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

A spacious living area features large windows allowing natural light to fill the room. A comfortable couch and a reclined chair offer seating, with a coffee table in front. A fireplace serves as a focal point, framed by decorative elements and bookshelves.

4.96 out of 5 average rating, 318 reviews

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

An aerial view of a spacious one-story home is surrounded by lush greenery and manicured lawns. A paved driveway leads to the entryway, providing ample parking. The home is set against a backdrop of trees and distant hills under a clear blue sky.

5.0 out of 5 average rating, 64 reviews

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.

An updated kitchen features stainless steel appliances, including a fridge and microwave, complemented by white cabinetry. A central island with metal stools provides additional workspace. A wooden cabinet displays dishware, and decorative plates are mounted on the wall, enhancing the room's functional design.

5.0 out of 5 average rating, 264 reviews

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.

A cozy living space features a brown sectional sofa adorned with a cushion displaying the phrase 'CALL ME OLD FASHIONED.' Green plants are positioned beside the couch, while patterned wall art and a decorative sign contribute to the inviting decor.

4.99 out of 5 average rating, 255 reviews

"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!

5.0 out of 5 average rating, 93 reviews

An open-concept living area features a cozy sofa and armchair, with light-colored walls and wooden beams above. The modern kitchen, equipped with stainless steel appliances and a spacious island, is complemented by bar seating and a view of the outdoors through a window.

Home in Crestwood

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!

4.9 out of 5 average rating, 155 reviews

Home in Jeffersontown

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.

A charming outdoor area features a multi-level deck with a bright umbrella over a seating area. Red Adirondack chairs are surrounded by lush greenery and flowering plants. A gazebo with string lights offers a cozy space for relaxation, while a pathway connects various sections of the garden.

5.0 out of 5 average rating, 34 reviews

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.

Guest house in Middletown

4.91 out of 5 average rating, 11 reviews

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.

5.0 out of 5 average rating, 52 reviews

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!

A stylish living area features a modern gray sofa accompanied by two blue accent chairs. A large flat-screen TV is mounted above a black fireplace. Natural light enters through multiple windows, which frame views of the surrounding greenery, enhancing the room's serene ambiance.

4.98 out of 5 average rating, 136 reviews

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.

The exterior of the home features a light beige facade with a metal roof and a vibrant red front door. Two shrubs frame the entrance, and the porch is accessed by three steps, providing a welcoming approach. Clear skies and lush greenery enhance the setting.

4.93 out of 5 average rating, 178 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.

Popular amenities for Middletown holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Middletown

4.76 out of 5 average rating, 58 reviews

A well-lit recreational room features a pool table at its center, surrounded by windows that allow natural light. Colorful pool balls are arranged on the table, and wall decor includes playful circular elements. A door leads to an outdoor space, enhancing accessibility.

Home in Jeffersontown

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

5.0 out of 5 average rating, 30 reviews

A modern kitchen features white cabinetry and a spacious island with seating for five. The countertops are finished in light stone, complemented by a neutral backsplash. Large windows provide natural light, and stainless steel appliances are neatly integrated into the design.

Flat in Prospect

Cozy Getaway at Norton Commons!

4.92 out of 5 average rating, 39 reviews

An open kitchen and dining area features modern appliances and a spacious dining table with multiple chairs. Sunlight pours through large windows, offering views of the outdoor landscape. A cozy seating area with neutral-colored cushions and decorative pillows is positioned nearby.

Home in Crestwood

Garden House, a private getaway

The lodge is surrounded by lush greenery, with a spacious deck extending from the upper level. A clear swimming pool, framed by manicured landscaping, is visible in the foreground. The two-story structure features large windows and a modern design, creating an inviting outdoor space.

4.92 out of 5 average rating, 66 reviews

Bourbon Country Lodge • 5 Acre Resort Pool+Hot Tub

4.98 out of 5 average rating, 80 reviews

An outdoor space features a newly built fire pit surrounded by several wooden chairs. Warm light illuminates the area, highlighting the green grass and shrubs in the background, while a two-story house is visible in the distance, framed by trees.

Home in Crestwood

Crestwood Louisville | Hot Tub | Bourbon Trail

5.0 out of 5 average rating, 3 reviews

Privacy to spread out, patio, TVs, pets, location

A split-level home is displayed, featuring a combination of brick and siding. A well-maintained garden with vibrant flowers lines the front. A mature tree provides shade, and the house is accented with dark shutters beside the windows. A welcoming sign is visible in the yard.

4.94 out of 5 average rating, 36 reviews

The Getaway!

The exterior of a large building features a welcoming entrance with a cupola atop the roof. The surrounding area includes manicured lawns and golf course greens, providing a scenic view of the landscape and open space for recreational activities.