Guest house holiday 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, 123 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, 105 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.

Guest house 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!

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, 309 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, 239 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.

4.97 out of 5 average rating, 136 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.)

A welcoming living area features exposed brick walls, highlighting a vintage painting. A leather sofa and a floral upholstered couch are positioned around a wooden coffee table. Natural light enters through tall windows, complemented by sheer curtains that gently frame the view.

4.98 out of 5 average rating, 160 reviews

Charming Carriage House in Old Louisville

Charming carriage house in historic Old Louisville neighborhood near Churchill Downs, convention center and downtown attractions. Unique, newly renovated space with 3 bedrooms, 3 queen beds/1 twin bed, 2 full baths each with shower, kitchen, patio/deck and 5G high speed internet. Also 2 Roku TVs with popular streaming channels like Fubo, Prime, Apple TV and Netflix, washer/dryer, parking spots at back of house plus on street parking in front of Carriage house.

A cozy sitting area is furnished with two slender armchairs and a small ottoman, placed on a decorative rug. A flat-screen TV is mounted on the wall, and a narrow table holds decorative items. Sliding doors lead into the bedroom, enhancing the open feel.

4.97 out of 5 average rating, 805 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.

A spacious living area features a comfortable sofa adorned with orange pillows, positioned on a patterned area rug. The open layout allows visibility into the kitchen, which includes wood cabinetry and dining space. A ceiling fan and light fixtures enhance the room's functionality.

4.91 out of 5 average rating, 147 reviews

St. Matthews Gem *Pinball *Private Parking

Welcome to your home away from home! This charming 2-bedroom house is located on our property but offers private access and private fenced area. The house features a pinball machine, board games, a Nintendo Switch, and an Xbox—perfect for relaxing after a day of exploring Louisville. Tucked away on a quiet dead-end street, this home offers private driveway parking and convenient highway access.

Guest house 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.

4.87 out of 5 average rating, 197 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.

4.93 out of 5 average rating, 1,096 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.

Superhost

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.

4.83 out of 5 average rating, 518 reviews

Carriage House Loft

Come enjoy our Carriage House loft located in the popular Louisville neighborhood of Crescent Hill. The loft is equipped with wifi internet, TV, and kitchen supplies. You will be within walking distance to some of the most popular establishments in Louisville; including Blue Dog Bakery, Clifton Coffee, and the Parlour Pizza. Short Term License # LIC-STL-24-00014

The spacious bedroom features a cozy bed with layered bedding and decorative pillows. An upholstered sofa in a soft yellow hue complements the room, while patterned wallpaper and eclectic decor add character. Natural light filters through sheer curtains, creating a welcoming ambiance.