Guesthouse vacation rentals in Jefferson County

An open kitchen and living area is displayed, featuring a stylish kitchen island with bar seating. A light-colored sectional sofa is arranged with a wooden coffee table, and an accent chair adds a pop of color. A piece of wall art is visible, enhancing the modern décor.

4.94 out of 5 average rating, 125 reviews

Carriage House - Crescent Hill (Frankfort Avenue)

Newly constructed carriage house in a charming historic community. Enjoy your own private getaway in the heart of Louisville's Crescent Hill neighborhood. This carriage house features an open kitchen / living concept with two private bedrooms (each has a comfortable queen bed) and a shared bathroom. In close proximity to local shops, restaurants, coffee shops and parks. Located less than 5 miles from downtown Louisville, less than 6 miles from the Expo center, less than 7 miles from the airport

5 out of 5 average rating, 111 reviews

A charming two-story brick guest house is set against a lush green lawn. The exterior features large windows and a welcoming front porch with two white chairs. A gently curving driveway leads to the entrance, framed by manicured shrubs and a nearby tree.

Guesthouse in Prospect

Prospect Guest House

Take it easy at this unique and tranquil getaway. Newly remodeled, new bathroom and kitchenette. We live in the house next door, but guest house is private and very quiet. Nestled in horse country-neighboring horses graze in adjacent fields. Queen bed upstairs, converted sofa queen in loft. Air bed also available. Lots of closet space, extra large bathtub, internet and streaming TV. Great location whether you are touring the Bourbon Trail or attending any of the The Kentucky Derby events!

4.92 out of 5 average rating, 235 reviews

A green barn structure with a metal roof is visible. The building features multiple windows and doors on the front, surrounded by well-kept grass and trees. A circular driveway approaches the barn, enhancing accessibility.

Guesthouse in Georgetown

Indian Creek Barn Cottage w/ EV & RV Charger

Private barn cottage in the knobs of Kentuckiana located on a 12 acre horse farm, recently renovated into a cozy comfortable space. The barn cottage is private space with 500 sqft, fully furnished 1 bedroom, 1 bath with living area, kitchenette equipped with a microwave, toaster, coffee maker, and mini refrigerator. Located just outside of New Albany, IN and less than 15 minutes to Louisville, KY allowing for the relaxation of the countryside, while also enjoying the city attractions!

An open concept living area presents a spacious layout with a red leather sofa and two black chairs surrounding a circular coffee table. A large Smart TV is mounted on the wall, and the area leads to a fully equipped kitchen, while natural light fills the space.

4.89 out of 5 average rating, 102 reviews

Chic Derby stay minutes from Churchill Downs!

A modern, open concept space will provide comfort and ease for your Louisville stay! This 2 bedroom, 1 bath apartment features a spacious living room with ample seating, a 65" Smart TV and 2 sleeper conversion chairs that sleep 2 extra people. There's a full kitchen, stocked bathroom, desk & washer/dryer for your convenience! Enjoy plenty of natural light equipped with room darkening shades for privacy. Conveniently located minutes from Downtown, Churchill Downs and the Highlands!

A charming balcony features a wooden table surrounded by four slatted chairs. A potted fern hangs gracefully from the angled ceiling, with views of lush greenery visible beyond the railing, creating a serene outdoor space.

4.98 out of 5 average rating, 318 reviews

Highlands Carriage House

Secluded Retreat in the Heart of the Highlands! Perfect for DERBY! Our carriage house is perfectly located in the heart of all Louisville has to offer. We are only steps from the finest dining, entertainment, pubs, shopping, parks, and coffee in Louisville. Bustling and eccentric Bardstown Road is only half a block away, yet the Carriage House feels secluded and very private. It is located 5 miles from Churchill Downs, 7 miles from the airport, and 2 miles from downtown.

A spacious bedroom features a large bed with dark bedding centered on wooden floors. Two cozy armchairs are positioned nearby, complemented by a vibrant area rug. A decorative mirror and framed artworks adorn the walls, while a bookshelf holds an array of books, adding character to the space.

4.96 out of 5 average rating, 241 reviews

Comfortable-relaxed space to find your inspiration

Located in the Germantown neighborhood of Louisville, this peaceful efficiency apartment in a traditional "shotgun" home, built in the 1890s, is within 10 minutes of nearly all of Louisville’s airport traveler’s attractions. Guests enjoy great sleep on top bedding and attention to detail. Sit on the front porch and let time slip by or spend the evening with a relaxing drink or meal in one of the neighborhood’s hip local eateries and bars. Plan your next journey.

The bedroom features a spacious king-sized bed, adorned with decorative pillows, and a stylish ceiling fan above. A wooden chest sits at the foot of the bed, complemented by a desk and chair in the corner. Natural light enters through window treatments, illuminating the room.

4.96 out of 5 average rating, 140 reviews

The City Cottage…quiet, peaceful, and convenient!

A quaint, cozy, and private space close to everything Louisville has to offer. Located on the Northeast side of Louisville, The City Cottage is near the highways for quick access to destinations in and around Louisville. This newly completed space is fresh, clean and created for guests in mind. Are you a couple traveling or a business person wanting more room and comfort than a typical hotel? The City Cottage is for you! (Three night minimum during Derby time.)

4.97 out of 5 average rating, 829 reviews

Germantown Carriage House w/garage

Germantown is a quaint neighborhood revitalized with restaurants, coffee shops and pubs. The carriage house has all the amenities for any length of stay, including garage parking with room for bikes. Only 2 miles from downtown Louisville, Germantown is nestled between the energetic and historic Highlands neighborhood, beautiful historic Old Louisville, and hipster NULU. Keyless entry makes for seamless check in and out.

Guesthouse in Mount Washington

A spacious outdoor area features a covered porch with seating options, including two lounge chairs and a large hammock. A charcoal grill is positioned nearby on a concrete surface. Lush grass surrounds the structure, providing ample space for outdoor activities.

4.78 out of 5 average rating, 445 reviews

Kentucky Derby Guest House

The Kentucky Derby guest house is an affordable place to stay that’s comfortable with plenty of room. Sleeps 6 comfortably with 3 queen beds w/ linens but there is plenty of room for more guests with SELF SUPPLIED air mattresses and bedding, we do not supply them. Great for an overnight stay on a road trip , or a multi day getaway while you’re in Kentucky visiting the Bourbon Trail.

Guesthouse in Jeffersonville

A serene bedroom features a spacious bed adorned with plaid and vibrant orange pillows. A bedside table with a small lamp sits next to a window, allowing natural light to fill the room. Inspirational wall art adds a personal touch to the calming blue backdrop.

4.86 out of 5 average rating, 213 reviews

Quiet & Quaint Carriage House: Sabai Sabai

Welcome to our lovely carriage house located in a quiet neighborhood in Jeffersonville, yet close to all downtown Louisville has to offer! You'll be in for a surprise when you're introduced to the relaxing and quaint living quarters that is "Sabai Sabai." Small town feel, big city access. You are only: 7 Minutes from the KFC Yum! Center 10 Minutes from NULU 15 Minutes from Churchill Downs

A blue carriage house is viewed from the driveway, surrounded by greenery and blooming trees. Steps lead to an upper balcony, offering outdoor potential. The driveway provides easy access to the garage, emphasizing a sense of space and privacy.

4.92 out of 5 average rating, 1,153 reviews

HIghlands Modern Get Away

Ideal, quiet place in the highlands. You have the apartment over the garage. You'll have a place all to yourself with most the amenities of your own home. Studio apartment with a balcony if you decide to hang out and relax for the evening. There is a cook top, but no oven in the kitchen. Park in the driveway in front of the garage. Pets are welcome, plz add them when booking.

A warm and inviting loft space features a spacious bed with dark green and white bedding, complemented by two pillows in yellow. A small round wooden table with two chairs sits nearby, with natural light filtering in through a window, enhancing the cozy atmosphere.