Guesthouse vacation rentals in Jefferson County

A modern kitchen features a sleek bar with five black metal stools arranged around it. The bar is positioned against a clean, white shiplap wall, complemented by a small potted plant placed centrally. A stainless steel refrigerator is visible in the background.

4.9 out of 5 average rating, 135 reviews

Cottage Park Carriage House. Rest w/Hollyhock

The Carriage house is located behind a historic mansion in beautiful Crescent Hill. Situated next to a park, this ideal location is still one block away from Frankfort Ave. shopping & dining, conveniently located near downtown, Churchill Downs, & four blocks from the Largest park in downtown Louisville. Newly designed and renovated-includes two separate bedrooms, office area, full kitchen, bathroom, & laundry. Free wifi, & parking. Refresh and relax in this satisfying getaway!

A charming carriage house features a peaked roof and a welcoming front entrance. A small wooden deck extends from the upper level, adorned with a railing. Lush green grass surrounds the structure, complemented by a decorative tree and hanging floral arrangement.

4.98 out of 5 average rating, 291 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.

4.91 out of 5 average rating, 545 reviews

Cute Carriage House off Frankfort Avenue

Welcome to "The Cute Carriage House at Frankfort Avenue". Experience serenity in a genuine "tiny house” that comfortably accommodates two people. There are several sleeping options that I will mention below. We are located a short block from premier restaurants and shops on Frankfort Avenue in the classy Clifton Neighborhood...and close to Cherokee Park and the cool Bardstown Road. FYI https://www.leoweekly.com/2020/10/the-winners-of-the-2020-readers-choice-awards/

A front garden displays vibrant orange flowers alongside lush green foliage. A yellow sign with red text is positioned among the blooms, while the steps leading to the entrance of the home are framed by stone edging. The entrance door is partially visible in the background.

4.96 out of 5 average rating, 232 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 bathroom features a modern sink vanity with two drawers and a large mirror above. A white toilet is positioned beside the vanity. Lighting is provided by three fixtures mounted above the mirror, and a small trash bin is located on the floor.

4.97 out of 5 average rating, 131 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.)

Guesthouse in Jeffersonville

A charming cottage features a stone exterior with decorative window boxes filled with flowers. A gravel path leads to the entrance, while a covered patio area is visible alongside the structure. The surrounding yard is spacious and green, offering a serene outdoor environment.

4.87 out of 5 average rating, 210 reviews

The Cottage Next Door

Looking for a cozy, clean place to rest your head while you explore? Comfort, simplicity and value- perfect for travelers who care more about adventure than luxury. We offer quiet, efficient and sparkling clean- everything you need to recharge after a day of soaking in the local sights, bites and vibes. We keep our prices low because we believe travel should be about the experience, not the expense. Book now and start your next adventure!

The exterior of a café is depicted, featuring a tan stone façade and a brown awning. Black metal patio tables and chairs are arranged in front of the entrance, shaded by large umbrellas. A sign with the café's name is prominently displayed beside the door.

4.96 out of 5 average rating, 763 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 pinball machine stands against a gray wall, adorned with colorful graphics. A cozy gray sectional couch is positioned nearby, complemented by a small yellow table. Natural light filters through a window, enhancing the inviting atmosphere of the entertainment space.

4.91 out of 5 average rating, 116 reviews

Prime Location, Private, games, pinball Fun!"

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.

Superhost

The entrance features a covered porch with a welcoming sign, providing space for seating and relaxation. Large windows allow natural light, while a basketball hoop mounted in the corner adds recreational options. A charcoal grill is available for outdoor cooking.

Guesthouse in Mount Washington

4.77 out of 5 average rating, 431 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 well-equipped kitchen features a blue island at the center and a mix of quality appliances, including a microwave and a refrigerator. Natural light is let in through large windows, illuminating the wooden floor and neutral-toned walls. Doorways lead to additional areas of the home.

4.86 out of 5 average rating, 177 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 presented, featuring a spacious driveway with a two-car garage below. A staircase leads to the upper level, framed by a tree dusted with snow, creating a serene winter scene.

4.93 out of 5 average rating, 1,009 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 landscaped outdoor space features a wooden deck with green chairs and a table, surrounded by trees and lush foliage. A fire pit is visible on the deck. In the background, a garage with blue siding is set within the tranquil yard, which includes play equipment.