Holiday rentals with a kayak in Jefferson County

4.99 out of 5 average rating, 155 reviews

The interior features a bunk bed with a twin upper and a full/queen lower mattress. A cozy seating area is provided with a round table and two orange chairs. Light enters through a nearby window, complementing the light-colored walls and flooring.

Tiny home in Louisville

Mugsy's Bunkhouse @ Progress Park Airstream Resort

Skip the packing & extra costs - everything you need is already here. Perfect for groups, families, or midweek getaways. This bunkhouse combines comfort, convenience, & a one of a kind outdoor experience. Enjoy your own private space PLUS access to boating, games, & more. All included with your stay. Show up, settle in, and start relaxing. Progress Park has 11 total units on site. 2 houses, 8 airstreams & this bunk house. *KY DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

4.95 out of 5 average rating, 368 reviews

A charming log cabin is framed by lush green trees, showcasing a warm exterior with a stone chimney. Rocking chairs are placed on the front porch, surrounded by vibrant flowers and a neatly maintained garden path leading to the entrance.

Cabin in Louisville

Captain's Cabin: Bourbon Trail, History & Romance

Your own log cabin on a wooded hillside with gourmet breakfast served to your door (on weekends)! It's been the location for 5 movies, including Lifetime! Period furnishings and modern conveniences make this an unforgettable retreat. A massive stone fireplace creates a quiet ambiance. Watch wildlife by the lake, creek or from back porch swings. Comfy bed, luxury sheets, high-speed internet, bluetooth stereo and special touches make your stay magical! Ask for Cooking With Bourbon Experience.

4.96 out of 5 average rating, 255 reviews

A modern kitchen space features white cabinetry and open shelving, displaying neatly arranged dishes and plants. A breakfast bar with four metal stools offers a casual dining area, complemented by a window that allows natural light to brighten the room.

Home in Louisville

502 House @ Progress Park w/ Game Room

Skip the packing & extra costs - everything you need is already here. Perfect for groups, families, or midweek getaways. The 502 house combines comfort, convenience, & a one of a kind outdoor experience. Enjoy your own private space PLUS access to boating, games, & more. All included with your stay. Show up, settle in, and start relaxing. Progress Park has 11 total units on site. 2 houses, 8 airstreams & a bunk house. *KY DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

Private room in Louisville

A vibrant living area presents a mix of teal and yellow walls, accentuating a stone fireplace. A wooden coffee table is positioned in the foreground, while a television and a dining area are visible in the background, creating an inviting communal space.

4.97 out of 5 average rating, 95 reviews

Bourbon Trail Beauty Basement Suite

You will enjoy a private room with a queen bed, a small private bath and my game room with pool table, dart board, games a large tv, an electric fireplace. and a bonus full bed. We are 5 blocks from Iroquois Park and just 2.3 miles to Churchill Downs and University of Louisville. I have kayaks you may rent as well as a bike to rent. My home has multiple bedrooms, so if you have more than 4 guests, check out one of my other room listings. I can host up to 8, if rooms are available.

The interior space of the Airstream showcases a modern design with reclaimed wood floors and white walls. A spacious kitchen features concrete countertops and various appliances. A cozy seating area includes a daybed, while the rear sleeping area is softly illuminated, creating a comfortable atmosphere.

4.97 out of 5 average rating, 335 reviews

The Grace Airstream at Progress Park in Derby City

Skip the packing & extra costs - everything you need is already here. Perfect for groups, families, or midweek getaways. The Grace combines comfort, convenience, & a one of a kind outdoor experience. Enjoy your own private space PLUS access to boating, games, & more. All included with your stay. Show up, settle in, and start relaxing. Progress Park has 11 total units on site. 2 houses, 8 airstreams & a bunk house. *KY DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

Superhost

A private bedroom is filled with warm tones, featuring a large wooden bed adorned with a floral-patterned comforter. A wooden chair complements the space, and natural light enters through a window with red floral curtains. Soft carpeting adds to the room's comfort.

Private room in Louisville

5 out of 5 average rating, 4 reviews

Captain's Annex: close to Bourbon Trail

Enjoy Louisville and bourbon country while staying in a private bedroom on a wooded hillside. Churchill Downs, 18 mi. Private entrance to your bedroom and private bath. On weekends, a hot gourmet breakfast is served on the wide front porch or eat in the log living room decorated with antiques and a massive fireplace. A Continental breakfast is served on weekdays. Take a quiet break with a walk along the pond or the creek. Try homemade bourbon balls. Get a taste of Kentucky!

The interior of the Airstream features a bright and modern layout. A well-equipped kitchen is visible on the left, including a stove and sink. A cozy sitting area with a light-colored couch is present, while a sleeping area is seen towards the back, adorned with soft bedding.

4.98 out of 5 average rating, 145 reviews

The Marie Airstream at Progress Park in Derby City

Marie is a 1996 Excella, perfect for groups, families, or midweek getaways.Skip the packing & extra costs - everything you need is already here. Maire combines comfort, convenience, & a one of a kind outdoor experience. Enjoy your own private space PLUS access to boating, games, & more. All included with your stay. Progress Park has 11 total units on site. 2 houses, 8 airstreams & a bunk house. *KY DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

A well-equipped kitchen area features modern appliances including a stove, oven, and microwave. A coffee maker is positioned on a wooden tray near a window, while bright cabinetry and smooth countertops create a clean, inviting space. Natural light illuminates the hardwood floor.

4.96 out of 5 average rating, 136 reviews

Stella Airstream at Progress Park in Derby City

Stella is a 1983 Classic, lovingly named after Airstream Founder Wally Byam's wife Stella! Perfect for groups, families, or midweek getaways. Stella combines comfort, convenience, & a one of a kind outdoor experience. Enjoy your own private space PLUS access to boating, games, & more. All included with your stay. Progress Park has 11 total units on site. 2 houses, 8 airstreams & a bunkhouse. *KY DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

The interior of the Airstream features a modern kitchen area, with white cabinetry and wooden countertops. A patterned wall adds a stylish touch. Natural light illuminates the space through windows, showcasing a clean and functional layout, including essential appliances and cooking supplies.

4.98 out of 5 average rating, 55 reviews

Yaya Airstream at Progress Park

Yaya is lovingly named after our owner Val's late mom. Perfect for groups, families, or midweek getaways. Everything you need is already here. Enjoy your own private space PLUS access to boating, games, & more. All included with your stay. Show up, settle in, and start relaxing. Progress Park has 11 total units on site. 2 houses, 8 airstreams & a bunk house. *KY DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

The interior of the Airstream showcases a modern layout with a cozy dining area featuring a dark table and beige seating. A spacious bed is visible in the background, complemented by neutral tones and warm lighting. Large windows allow natural light to fill the space.

5 out of 5 average rating, 155 reviews

The GiGi Airstream, Lakeside at Progress Park

This Gigi is a 2022 Airstream Flying Cloud w/ all the bells and whistles. Everything you need is already here. Perfect for groups, families, or midweek getaways. Enjoy your own private space PLUS access to boating, games, & more. All included with your stay. Progress Park has 11 total units on site. 2 houses, 8 airstreams & a bunk house. *KY DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

A stately two-story home is framed by manicured lawns and trees. The façade features large windows, a centered doorway with a porch, and classic black shutters, creating an inviting entrance. A clear blue sky complements the serene outdoor environment.

Home in Louisville

The Country Chic Cottage

Relax in this updated 4‑bed home with tons of space and fun for all ages. Enjoy a finished basement with games, gym, and big‑screen TV, plus a huge deck with smoker, grill, and outdoor dining. Three living areas, comfy bedrooms, and a kid‑friendly yard with trampoline, playhouses, and sports goals make this the perfect East Louisville getaway.