Apartment holiday rentals in Madisonville

The Brokerage Main Street Loft

Welcome to the biggest, most luxurious loft apartment in the entire area! With 12 foot ceilings, soaring original windows, 150 feet of exposed original brick walls. a massive 9x5 island and counters made from 140 year old heart pine wood, this is the perfect spot for family and friends in downtown Henderson. We can set up a queen Murphy bed upon request in the big master suite for extra company. Restaurants, shops and the famous Ohio River Walk are within 1 block. Find small town luxury here!

The Mint Julep! Upstairs 3BD/2BA - Next to Brewery

Book your stay at The Mint Julep and experience Henderson like a local. Fresh vibes, classic charm, and a stay worth toasting. You are "mint" to make memories at The Mint Julep. Welcome to The Mint Julep, a stylish and spacious upstairs retreat in the heart of Henderson, Kentucky! This 3-bedroom, 2-bath rental is perfectly located adjacent to Henderson Brewing Co., near Holy Name Church, and just a short walk from downtown restaurants, shops, riverfront attractions, and seasonal festivals.

Suburban Chateau

Located roughly a mile from city limits, this spacious and serene duplex offers a comfortable retreat with easy access to nearby attractions while still providing a peaceful setting. Guests will have exclusive use of their unit, including a separate driveway and private entrance. Please note, this is a duplex. Accommodates up to 4 guests max -Farmer & Frenchman • 3.7 miles away -Holiday World • 43 miles away -Sloughs Hunting State Land • 12 miles away -Sandy Lee Watkins • 9.6 miles away

Country Charm Luxury Waterfront Apartment w/ Dock

Beautiful waterfront home with private dock on Lake Barkley. Our custom built house has a completely finished and immaculate basement apartment with a patio overlooking the lake. This apartment is a private basement apartment in our home with private access. We will likely be around and would be glad to meet you to give you the key. The professionally decorated apartment features a living room with a fireplace, TV, and WiFi, a kitchenette, and has 3 bedrooms and 2 baths.

Modern, Quiet, Hidden Gem: Manna House (7)

Kick back and relax in this peaceful, brand new, stylish space. Located close to town yet feels like a hidden country paradise. This unit is one of two units available at a duplex situated on 5 acres. With 10 foot ceilings, this one bedroom feels so much bigger! It offers a walk in tile shower, queen size adjustable bed, queen size sleeper sofa, full kitchen with Quartz countertops, KitchenAid appliances, and includes full size stacked washer/dryer. We think you will love it here!

Cozy Downtown Studio Apartment

Enjoy a stay in this centrally located downtown studio apartment right in the heart of historic Hopkinsville. The apartment is fully furnished with a queen sized bed, a full couch, two-person dining table, and in-unit washer and dryer. Within walking distance of downtown shops and restaurants. Private entrance to the second story apartment (no elevator). *Note: This studio apartment does not have windows - perfect for third shifters, night owls, gamers, or vampires!

The Guest House at Kate & Waverly

Welcome to the Guesthouse at Kate & Waverly! This beautiful historic building, built in 1902, is located in downtown Owensboro. We are walking distance to many downtown restaurants and bars, as well as the Convention Center, Bluegrass Music Hall of Fame, Bluegrass Fieldhouse, and the beautiful Ohio riverfront and park. The AirBnB is located on the second floor above Kate & Waverly—a gift shop with unique vintage and antique finds, as well as an interior design center.

The Shire Apt 1

I think you'll be surprised at what this little apartment has to offer. This apartment is perfect for the traveling professional who would like a place of their own without having to pay for a costly hotel. If you're looking for a quaint quiet little place, this apartment is perfect. If you're looking for a five-star hotel then there are plenty of other of listings with prices to match. Our rental starts at 5 to 7 days with offers to extend for as long as you need.

Bluegrass Hideaway

Cozy 2-bedroom, 1-bath retreat perfect for families, friends, or business travelers. Sleeps 4 comfortably with plush bedding. Fully equipped kitchen, spacious living area, high-speed WiFi, and Smart TV for entertainment. Fresh towels and toiletries provided. Free parking available. Conveniently located near restaurants, shopping, and local attractions. Experience comfort and convenience in a relaxing space. Book your stay today!

Apt 3 - Furnished 2 bdr 2nd floor Apartment

This is Apt 3 of a 5 unit Apt building that has been converted into 5 airbnbs. Each unit is 2 bdrm 1 bath. It includes full kitchen, dishes, silverware, pots/pans, stove, microwave, refrigerator, dishwasher, coffee maker, washer/dryer, and a smart TV. Each bedroom has a queen bed. Towels, bedding, etc.. are included. You dont need to bring anything. Free Wifi comes with each unit. There are no shared spaces between units.

River House Suite

This special place is close to everything, making it easy to plan your visit. Walking distance to Downtown Owensboro’s Bluegrass Hall of Fame, Riverpark Center and the Convention Center. Peaceful culdesac with a nice view of the Ohio River from the spacious deck where you can barbeque or just relax and watch the river roll by. Walk a few steps to the rivers edge for a look at the Blue bridge and Owensboro's Riverfront.

Liberty Hall Guest Suite

The Guest Suite at Liberty Hall in historic Elkton, Kentucky is a beautiful place to unwind. Guest favorites include the lovely antique furnishings and the porch swing on the private wrap around porch. If interested, the owners will gladly give a tour of the other areas of the home and tell the history of the property.