Vacation rentals with a fireplace in Middletown

Chic Cabin w/ Trails, Hot Tub & Starry Nights

Privately nestled on over 5 wooded acres & intentionally curated for your stay. Gain access to quiet, immerse yourself in nature, support your rejuvenation, & to tap into your creative flow. Amenities include on-site hiking trail, artist work space, wood burning stove, covered porch, hammocks, outdoor dining, fire pit, moon garden, salt-water hot tub, & outdoor shower. Close to Beaver Lake & located along the Bourbon Trail, just minutes from Wild Turkey & Four Roses distilleries. (Note:18+only)

Bourbon Trail Cabin~Enjoy Christmas decor in Dec!

🌲FOR CHRISTMAS- home is transformed into cozy holiday cabin retreat! A charmingly unique taste of KY waits for you at this peaceful log cabin! Perfect for those wanting to explore the 🥃Bourbon Trail🥃 or other nearby tourist attractions, While still featuring plenty of fun on site, such as: - A hot tub - Private 1/4 mile hiking trail - Game shed - Fire pit - Covered porch - Wooded picnic area And more! Your next adventure is just a peaceful countryside drive away at the Kentucky Bourbon Den!

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

Peppermint Cottage Norton Commons w Breakfast

Step into Peppermint Cottage and find the perfect blend of convenience and charm! Just 20 minutes from SDF airport, Churchill Downs, and downtown Louisville's excitement, this trendy east end haven offers an irresistible walkable lifestyle. Stroll or bike to 18 mouth watering restaurants, 14 unique boutiques, and YMCA with pool. Enjoy lakeside fishing, Sunday farmers markets, summer concerts, parks and Friday food truck festivities. Your ideal Louisville adventure awaits at Peppermint Cottage!

ArTisTs CoTTaGe

Enjoy peaceful privacy with center city convenience! Bright, open ambiance. Art and music supplies, books, toys, games, CD's, movies. Two decks and a covered patio. Found art gardens and galleries. Fully equipped kitchen with granite counters. Large windows in downstairs bedroom with queen bed and gas fireplace. Ladder access to queen bed in skylit loft. A perfect getaway for artists/writers on retreat, solo adventurers, couples, business travelers and small families with well behaved kids.

Captain's Cabin: Bourbon Trail, History & Romance

Your own log cabin on a wooded hillside with gourmet breakfast served to your door (on weekends)! It's been the location for 5 movies, including Lifetime! Period furnishings and modern conveniences make this an unforgettable retreat. A massive stone fireplace creates a quiet ambiance. Watch wildlife by the lake, creek or 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.

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.

The River's Edge Oasis, close to downtown

Welcome to your oasis on the water! Relax and unwind at the River's Edge. This home is about as close as you can get to paradise in Louisville Ky (also known as River City)! Perfect getaway for a romantic weekend or the best place to relax after a long day of work! Voted #1 Vacation rental in KY by Dreamy Stays!! This unique home is designer decorated and updated with all the amenities! An 8 minute drive to downtown Louisville, the oasis offers the best of both worlds. Book today!

Private EAST END gem, minutes to 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.

4th Street Suites - Extravagant King Bed Suite

Wake up to the best of Louisville! Imagine starting your morning in a cozy king bed, strolling to 4th Street Live for brunch, and exploring nearby restaurants, bars, and theatres. Spend the afternoon lounging by the pool or soaking in the hot tub, then watch the city lights twinkle from the 7th‑floor terrace. This stylish suite is your launchpad for urban adventure—and a quiet, relaxing escape when it’s time to rest. Come make it yours and experience the heart of the city!

Cottage of Eden. Bourbon Trail Stay in Shelby Co.

Listen to the birds sing as the walkway guides you to your quaint cottage getaway. Take in nature, as you’re surrounded by trees, near our sweet chicken coop and a creek that flows down from the deck - all while only 10min from town. Special touches were added of Kentucky Derby photos, books, kitchenware, Bourbon Trail glasses and bourbon barrel heads with local distilleries. The dining table top is even made of wood from Shelby County’s own Bulleit Distilling Company.

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.