Simpsonville holiday homes

We found 140 holiday rentals — enter your dates for availability
Discover a selection of 11 homes and other holiday rentals in Simpsonville that are perfect for your trip. Holiday homes offer the best amenities for your family, friends or furry companion, such as parking and a washer and dryer. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Simpsonville

Showing deals for:8 Jan - 15 Jan

Interior
Exterior
Private kitchen
Property grounds
Exceptional
(5 reviews)

Restored 1919 Farmhouse on 100 Private Acres

Simpsonville

8% off
NZ$3,935
for 7 nights, 1 room
NZ$562 per night
includes taxes & fees
Restored 1919 Farmhouse on 100 Private Acres
Dining
Exterior
Interior
Living area
Exceptional
(13 reviews)

4Br Home on Sabre Hill Horse Farm 25 acres ~ Bourbon Trail

Simpsonville

8% off
NZ$7,091
for 7 nights, 1 room
NZ$1,013 per night
includes taxes & fees
4Br Home on Sabre Hill Horse Farm 25 acres ~ Bourbon Trail
Exterior
Interior
Dining
Private kitchen
Exceptional
(6 reviews)

Historic Home Farm Stay in the Heart of Bourbon Country

Shelbyville

8% off
NZ$9,620
for 7 nights, 1 home
NZ$1,374 per night
includes taxes & fees
Historic Home Farm Stay in the Heart of Bourbon Country
Terrace/patio
Kitchen view 2
Master bedroom view 2
Kitchen view 3
Exceptional
(49 reviews)

Unique Serenity - Entire Home On Private 3-Acres in Metro. Expo Center, Bourbon

Louisville

7% off
NZ$5,755
for 7 nights, 1 home
NZ$822 per night
includes taxes & fees
Unique Serenity - Entire Home On Private 3-Acres in Metro. Expo Center, Bourbon
Living area
Room
Living area
Private kitchen
Exceptional
(43 reviews)

Historic 1909 Gem on the Bourbon Trail w/4 King Beds

Shelbyville

7% off
NZ$4,064
for 7 nights, 1 home
NZ$581 per night
includes taxes & fees
Historic 1909 Gem on the Bourbon Trail w/4 King Beds
Exterior of House
Kitchen
Living Area
Downstairs Living
Exceptional
(7 reviews)

Shelbyville, KY - Bourbon Trail, Horse Country and more. A modern, spacious gem.

Shelbyville

8% off
NZ$3,627
for 7 nights, 1 home
NZ$518 per night
includes taxes & fees
Shelbyville, KY - Bourbon Trail, Horse Country and more. A modern, spacious gem.
Brand new dining room with views of deck, side and backyard.
View from kitchen toward dining room.
Charming living room with a sleeper sofa, YouTubeTV, and plenty of seating.
Back of house with new walkway and deck.
Exceptional
(87 reviews)

Charming house in one of Louisville's most coveted neighborhoods

Louisville

8% off
NZ$3,449
for 7 nights, 1 home
NZ$493 per night
includes taxes & fees
Charming house in one of Louisville's most coveted neighborhoods
Walkout basement sleeping area. Note: This is an Unfinished Basement.
Living Room, Breakfast area. Kitchen is to the right.
Friendly front porch.
Catwalk adjoins the upstairs bedrooms.
Exceptional
(57 reviews)

Near Highways and a 20 Min Drive to Louisville's Main Attractions

Louisville

7% off
NZ$5,154
for 7 nights, 1 home
NZ$736 per night
includes taxes & fees
Near Highways and a 20 Min Drive to Louisville's Main Attractions
Room
Terrace/patio
Living area
Living area
Exceptional
(23 reviews)

Enchanted Cabin at LedgeRock Springs

Louisville

7% off
NZ$7,581
for 7 nights, 1 cabin
NZ$1,083 per night
includes taxes & fees
Enchanted Cabin at LedgeRock Springs
Interior
Exterior
Room
Private kitchen
Exceptional
(11 reviews)

The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade Barn, Sleeps 12+

Shelbyville

13% off
NZ$7,505
for 7 nights, 1 cabin
NZ$1,072 per night
includes taxes & fees
The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade Barn, Sleeps 12+
Living area
Exterior detail
Room
Exterior detail
Exceptional
(9 reviews)

Bourbon Trail Retreat . Sleeps 10 + Hot Tub. In the Heart of the Bourbon Trail

Shelbyville

7% off
NZ$4,729
for 7 nights, 1 home
NZ$676 per night
includes taxes & fees
Bourbon Trail Retreat . Sleeps 10 + Hot Tub. In the Heart of the Bourbon Trail

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Simpsonville getaway

Learn about the unique charm of Simpsonville with a stay in a holiday home rental. This city has something for everyone. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Sightseeing in and around Simpsonville

Are you looking for attractions to see while you're in the area? Venture out of your cosy holiday rental and check out everything that makes Simpsonville a fun spot to go on holiday. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Valhalla Golf Club (7.1 mi / 11.4 km)
  • Louisville Zoo (19.4 mi / 31.2 km)
  • Talon Winery (4.5 mi / 7.3 km)
  • Polo Fields Golf and Country Club (6.1 mi / 9.9 km)
  • Eagle Creek Golf Course (12 mi / 19.3 km)
  • Long Run Golf Course (5.7 mi / 9.2 km)

Exploring the natural features in Simpsonville

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Simpsonville is a great spot to appreciate mother nature. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Beckley Creek Park (6.8 mi / 11 km)
  • Yew Dell Botanical Gardens (10.8 mi / 17.4 km)
  • Ohio River Valley (12.3 mi / 19.7 km)
  • E.P. Tom Sawyer State Park (12.5 mi / 20 km)
  • Taylorsville Lake State Park (13.5 mi / 21.7 km)
  • Taylorsville Lake (15.9 mi / 25.6 km)

Transport options to and around Simpsonville

The nearest airport is in Louisville International Airport (SDF), located 21.4 mi (34.5 km) from the city centre.

Frequently asked questions

What is the best area to stay in Simpsonville when booking a holiday rental?
When considering a holiday rental in Simpsonville, Kentucky, a popular area to stay is near the charming downtown. This location offers a delightful blend of convenience and local character, with several properties available that provide easy access to the town's amenities. The downtown area is home to quaint shops and eateries, allowing visitors to experience the local culture.Another appealing option is the vicinity of the historic sites and the surrounding countryside, which features beautiful landscapes and tranquil settings. This area not only provides a peaceful retreat but also proximity to attractions such as the nearby Kentucky Bourbon Trail, which is superb for those looking to explore the region's rich distilling heritage.For those who enjoy outdoor activities, the nearby parks offer picturesque walking trails and picnic spots, making it an excellent choice for families and nature enthusiasts alike.
What is the most popular type of holiday rental accomodation in Simpsonville?
In Simpsonville, holiday houses and cottages are the most popular types of holiday rentals, with several options available throughout the area. These properties often feature spacious interiors, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many rentals also provide outdoor spaces, such as patios or gardens, great for enjoying the pleasant Kentucky weather.
Are there any family house rentals in Simpsonville?
In Simpsonville, Kentucky, there are several family-friendly house rentals available, making it a wonderful choice for those travelling with children. Many of these homes are situated in peaceful neighbourhoods, providing a safe environment for families. Visitors can expect spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play or enjoy a barbecue.The town is conveniently located near attractions such as the Kentucky Horse Park and the beautiful parks that offer walking trails and picnic areas. Additionally, families can explore nearby farms, which often host seasonal activities, creating memorable experiences for all ages.
Are there any remote work holiday rentals in Simpsonville?
In Simpsonville, Kentucky, there are several remote work holiday rentals available, making it a suitable destination for those looking to combine work and leisure. Many of these properties come equipped with essential amenities for remote work, including dedicated desk spaces and reliable Wi-Fi, ensuring that guests can stay productive during their stay.The town itself offers a charming environment, with nearby parks and recreational areas providing opportunities for relaxation and outdoor activities after work hours. Additionally, the local community features quaint shops and restaurants, adding to the appeal for long-term stays. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Simpsonville?
In Simpsonville, popular rental amenities include well-equipped kitchens, which allow travellers to prepare their own meals conveniently. Onsite parking is also a common feature, providing ease of access for guests with vehicles. Many rentals come with coffee and tea makers, great for a quick morning brew. Additionally, properties often feature decks or patios for outdoor relaxation, as well as desks that cater to those needing a workspace during their stay.
When is the best time to visit Simpsonville for a holiday rental?
The peak season for visiting Simpsonville falls between June and August, when the warm summer weather makes it ideal for outdoor activities and local events. July stands out as the most popular month, bustling with visitors eager to explore the charming town and its surrounding attractions. During this time, you can enjoy the vibrant setting, with opportunities for hiking, picnicking, and experiencing the local culture.In terms of climate, you can expect pleasant temperatures averaging around 25 to 30 degrees Celsius, great for enjoying outdoor adventures or simply relaxing in the sun. The long daylight hours allow for ample sightseeing, whether you're wandering through local parks or visiting nearby attractions.For those looking for a more budget-conscious option, January offers a quieter experience in Simpsonville. While it's the low season, this month presents a unique opportunity to enjoy the town's winter charm without the crowds, allowing for a more relaxed pace and the chance to explore local eateries and shops at your leisure.Whichever month you choose to visit, Simpsonville welcomes you with a variety of experiences, making it a delightful destination for a holiday rental.
What are the top attractions in Simpsonville?
In Simpsonville, Kentucky, visitors can explore several attractions that highlight the charm of the area. The nearby Kentucky Bourbon Trail is a major draw, with various distilleries offering tours and tastings, showcasing the region's rich bourbon heritage. The town itself features beautiful parks, such as the Simpsonville Park, which provides walking trails, picnic areas, and playgrounds, making it a great spot for families.Additionally, the nearby Red Orchard Park is known for its scenic walking paths and community events, offering a lovely outdoor experience. For those interested in shopping or dining, the local area has a selection of charming boutiques and restaurants that showcase Kentucky's culinary delights.
Are all fees included in the Simpsonville holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Simpsonville holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Simpsonville with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Simpsonville holiday homes?
You can find great discounts on holiday homes in Simpsonville on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Simpsonville holiday home booking on Bookabach?
To find Simpsonville holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Simpsonville?
A long-stay holiday home in Simpsonville is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Simpsonville holiday home?
Book your Simpsonville holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Simpsonville?
Prices for holiday homes in Simpsonville vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Simpsonville to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.