Guesthouse holiday rentals in Jefferson County

4.94 out of 5 average rating, 120 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

4.92 out of 5 average rating, 306 reviews

Charming Carriage House with 2 private baths.

Our home and Carriage House in is an extremely nice, safe beautiful neighborhood. I know many guests including myself are even more concerned with cleanliness. Rob and I have always taken extreme pride in assuring our guest house is spotless. However, we have taken it up another notch. We have purchased a Utilizer that sanitizes areas with it's ultraviolet light. We use this machine after each guest to ensure the air and every surface is sanitized. It is truly home away from home!!!

4.93 out of 5 average rating, 230 reviews

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!

4.98 out of 5 average rating, 306 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.

4.96 out of 5 average rating, 238 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.

4.97 out of 5 average rating, 133 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.)

4.96 out of 5 average rating, 797 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.

4.91 out of 5 average rating, 143 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.

Guesthouse in Jeffersonville

4.86 out of 5 average rating, 190 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

4.92 out of 5 average rating, 1,074 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.