Holiday rentals in Pioneer Village

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Pioneer Village

Guests agree: these stays are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Tiny home in Shepherdsville

4.93 out of 5 average rating, 229 reviews

Tiny House Near Louisville

The tiny house is 200 square feet, but has everything you need for a cozy stay! It’s located inside our half acre fenced in backyard which is right off I-65 and is 15 minutes to downtown Louisville. Fast food, restaurants, gas stations, and laundry mat are less than a mile away. The backyard is a shared space with us, so there’s a small chance you see us or our friendly dogs out there. We built the tiny house ourselves, so we take pride in it and hope you choose to experience tiny house living!

Guest favourite

Cabin in Louisville

4.95 out of 5 average rating, 340 reviews

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 4 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.

Top guest favourite

Home in Shepherdsville

5 out of 5 average rating, 12 reviews

Cozy Home Near the Bourbon Trail & KY Derby

Welcome to our spacious 4-bedroom home, located between Kentucky’s iconic Bourbon Trail and all that Louisville has to offer. Just a few minutes drive to I65 close to E-town, Bardstown or Louisville. Nestled in a small, quiet neighborhood, comfortable and convenient for families, friends, or groups looking to explore the heart of Kentucky. Whether you’re here for bourbon, events, the Kentucky Derby, or relaxation, this home is your perfect getaway. Book now to make unforgettable memories!

Top guest favourite

Cabin in Louisville

5 out of 5 average rating, 214 reviews

Historic Cabin by Bourbon Trail

Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

Top guest favourite

Campervan/Motorhome in Louisville

4.97 out of 5 average rating, 119 reviews

The Pearl Airstream at Progress in Derby City

Meet our Pearl Airstream. She's a 1989 Squarestream. That's right, a SQUARE Airstream! There were less than 300 made from 1989-1991, so this is your chance to stay in one of very few in existence! She sleeps 4, possibly 5 depending on your comfort level. There's a private bath/shower. You'll have a kitchen & covered patio with grill & firepit. There are 11 total units on site. 2 houses, 8 airstreams & a bunk house. *DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

Top guest favourite

Flat in Louisville

5 out of 5 average rating, 42 reviews

Cozy Garage Apt- Country Charm with City Amenities

We invite you to enjoy city amenities in a country setting. Nestled in the heart of Fern Creek on Louisville's southeast side, our location is a convenient drive to most places with many nearby restaurants. Come leave the hustle and bustle behind as you enjoy a peaceful stay. This space is a studio apartment, one open room except for the bathroom. The apartment is located above our two car garage. You will enter through the side door. This apartment is accessed by a set of stairs.

Guest favourite

Serviced apartment in Louisville

4.94 out of 5 average rating, 62 reviews

ground level flat with washer-dryer & easy parking

This super adorable and stylish new flat is nestled on the ground floor of a duplex in the community of Zoneton. You'll have convenience of being only 17 minutes from Downtown Louisville, while enjoying a peaceful country style suburb setting. The great room boasts a fully accessorized kitchen, pull out queen sofa with memory foam & a 50" smart TV. The bedroom has a queen bed and smart TV. Included are a washer/dryer & walk-in closet. There is fiber optic WIFI & Netflix.

Guest favourite

Cottage in Coxs Creek

4.96 out of 5 average rating, 142 reviews

Bourbon Trail Cottage

Unique cottage nestled in the woods located along the Bourbon Trail. Centrally located near miles of nature trails in Bernheim Forest & many of the distillery tours. Yet lots of privacy on 10 wooded acers. 8 minutes to Jim Beam Distillery, 8 min to Bernheim Forest, 4 min to Four Roses Bourbon Warehouse & Bottling Tour, 12 min to the City of Bardstown, 30 min to Churchill Downs, 26 min to Louisville International Airport (SDF) NO SMOKING NO PETS

Top guest favourite

Dome in Mount Washington

4.98 out of 5 average rating, 172 reviews

My Old Kentucky Dome

An elevated camping “glamping” experience. This brand-new one of a kind geodesic dome is located on a private road that leads you to an overlook featuring one of the most beautiful countryside views in Kentucky. While this getaway experience is nestled deep in the woods, it is also a close drive to all the conveniences you can imagine. This is an off the grid outdoor experience with a ½ mile gravel road including a steep hill. AWD or 4WD advised.

Top guest favourite

Flat in Mount Washington

4.95 out of 5 average rating, 202 reviews

“Crossroads” connecting Louisville and Bardstown

This apartment is good for couples, solo adventurer and business travelers. It is 10 miles south of Louisville, 18 miles north of Bardstown, 18 miles west of Taylorsville Lake and 1 hr away from Lexington. It is close to a very cool park, The Parklands, where you can hike, bike and kayak. The apartment is centrally located in the “crossroads” of several really cool communities in horse country, Kentucky.

Top guest favourite

Guest suite in Louisville

4.96 out of 5 average rating, 163 reviews

One Room Apartment with Private Off Street Parking

Room is a stand alone efficiency with a kitchenette, blackout curtains, and reclining queen bed. It has one designated parking space and seperate entrance. Unit has private bath and walk in closet, and kitchenete. Also has refeigerator, coffee maker, work desk microwave, 42" smart tv, Ninja airfryer oven, and couch. Private porch with table and chairs. Close/secure single parking space.

Guest house in Mount Washington

4.77 out of 5 average rating, 432 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.