Vacation rentals in Simpsonville

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Top-rated vacation rentals in Simpsonville

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

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Guest favorite

Cottage in Taylorsville

4.89 out of 5 average rating, 122 reviews

Best view of the lake two bed two bath cottage #4

Martha GraceRating, 5 stars6 months ago

Kim helped me get reservations set up for my parents anniversary, for the second year in a row. She is extremely kind and helpful, and my parents loved her place and the area so much they went back! Very clean and nice place, plenty of extra amenities, beautiful views of the lake and surrounding area and wildlife, good restaurants within driving distance, and plenty of privacy and a feeling of safety and calm! Thank you again Kim from all of us, especially my very happy parents!

Guest favorite

Home in La Grange

4.93 out of 5 average rating, 105 reviews

Hot Tub-King Bed-Coffee Bar-Arcade-Fire Pit!

JustinRating, 5 stars2 weeks ago

Stayed a week for a family trip around Louisville. We appreciated the nice, affordable stay. Plenty of room for the 4 of us. Location is great as it’s very close to downtown LaGrange. Great little town! We enjoyed our stay!

Top guest favorite

Cottage in Taylorsville

4.96 out of 5 average rating, 194 reviews

Four Seasons Cottage at Taylorsville Lake KY

EricRating, 5 stars1 month ago

Great “home base” for our trip to Louisville. Home matched the description and was very clean and nicely decorated. Very quiet neighborhood during our stay. Close to a great state park for hiking. Host was very proactive with instructions and helpful information.

Top guest favorite

Cabin in Mount Eden

4.98 out of 5 average rating, 143 reviews

Bourbon Country Cottage

TheodoreRating, 5 stars3 weeks ago

The opportunity for me and my brother to enjoy the NCAA tourney while cooking on the grill, enjoying bourbon bought after our tour of Buffalo Trace distillery, all the while taking in the vast landscape by the fire pit and enjoying the Western Kentucky breeze and sunset. If you are looking for a true get away and enjoying a vaca solo or with loved ones this is the spot for you. Just wish we had bought more bourbon and firewood cause both never lasted long enough enjoying the conversations and the night sky. Definitely one for the memory books.

Guest favorite

Home in Bardstown

4.92 out of 5 average rating, 138 reviews

McIntyre’s Country Getaway

MichelleRating, 5 stars9 months ago

This home was perfect for 3 couples. Living room furniture was very comfortable! We all want to buy those couches now. Very nice setting, and enjoyed the winery literally in the backyard. Host was very friendly and even brought us fans for the bedrooms that didn't have them. Will definitely stay again in the future. Close enough to Bardstown activities but far enough away to feel private and secluded at the same time.

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What guests are saying

Sweet Southern Comfort 3 Qn bd 2+bth sleeps 6

4.97 out of 5 average rating, 33 reviews3 weeks ago

The house was perfect for our needs! We were partaking of the bourbon trail and were also able to work a thoroughbred tour at Winstar farms in as well - would highly recommend. The decor and floor plan is very comfortable and inviting. The porch out back was very nice for a nosh and a glass of wine. We walked easily to town central for dinner. We had a delicious cocktail at Liam Ash. The server there was a wealth of information about bourbon culture. There are many great restaurants in town too. Paula is an excellent host and we hope to return soon - thank you!

Home in Bardstown

What guests are saying

2King beds+HotTub+FirePit

4.97 out of 5 average rating, 36 reviews1 week ago

This Kentucky home is a perfect place to stay for visiting Bourbon country. Great location, short drive to restaurants. The house is beautiful and well stocked. All the bedrooms are upstairs, so if stairs are a problem this might be a consideration. Peaceful, beautiful backyard. The hosts are very responsive and helpful.

Home in Crestwood

What guests are saying

Bourbon Barrel Cottages #4 on the Kentucky Bourbon Trail

4.99 out of 5 average rating, 70 reviews3 weeks ago

We stayed one night in the cabin on our way home from Gatlinburg. It was the favorite part of our trip! The cabin was beautiful, thoughtfully stocked with everything we could need. Beautiful and secluded surroundings. We will be back for sure!

Home in Lawrenceburg

What guests are saying

Eire Cottage Hot Tub & Private Waterfall Luxury

4.95 out of 5 average rating, 37 reviews2 weeks ago

Wow! If I could give Brandan more than 5 stars, I would! Her home is so cozy and peaceful! She had everything there a guest would need or never think of needing and available! Her home is spotless! The instructions she gave us were on spot! We were there during the record breaking floods of Frankfort and never had a problem at the house. She offered so many suggestions after finding out a few of our tours were cancelled. Thank you Brandan for a memorable stay with our friends!

Home in Frankfort

What guests are saying

Bourbon Trail Beauty

5 out of 5 average rating, 14 reviews1 week ago

Outstanding! Beautifully decorated. Pristine. Great neighborhood with easy walk to several really nice restaurants. We visited with four couples and everyone was totally comfortable. The pictures don't really do justine to how beautiful and spacious this home is. Equipped with everything we needed.

Home in Versailles

What guests are saying

Top of the Rock

4.99 out of 5 average rating, 67 reviews1 month ago

Great place with responsive hosts. Our family loved the property, the views, and the area. We hiked around the state park trails there onsite, explored the little chapel, grilled out, ate around the fire pit, ate at The Chicken House, hiked around Charlestown State Park, watched a lot of March Madness, and just enjoyed being together.

Chalet in Borden

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Popular amenities for Simpsonville vacation rentals

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Stay near Simpsonville's top sights

The Outlet Shoppes of the Bluegrass66 locals recommend

Bass Factory Outlet4 locals recommend

Brick+Mortar Boutique and Coffeehouse3 locals recommend

Other great vacation rentals in Simpsonville

Superhost

Home in New Albany

4.88 out of 5 average rating, 59 reviews

Modern Townhome on Mansion Row w/Pool Table

KellyRating, 5 stars4 months ago

The house was beautiful and exactly what was described. We messed up and locked ourselves out and they took care of that very quickly for us. Very nice area in downtown. When we go back again we will see if it is available and book there again. Thank you!

Top guest favorite

Home in Louisville

5 out of 5 average rating, 10 reviews

Derby House with Hot tub and King Bed

MattRating, 5 stars1 month ago

We really enjoyed our time here. It’s very convenient to all the Louisville attractions. Check and process was very easy and the house was very clean. There were great restaurants nearby. In a very friendly neighborhood. Johlandi was very responsive, she is an excellent host.

Top guest favorite

Home in Louisville

5 out of 5 average rating, 12 reviews

Bourbon City Bungalow

NoahRating, 5 stars3 weeks ago

Daniel was very helpful with accommodating my family. The place was just as described and super nice. Lots of local restaurants and shops close by

Guest favorite

Home in Harrodsburg

4.91 out of 5 average rating, 118 reviews

Private Cabin on Bourbon Trail with Hot Tub

KarleyRating, 5 stars3 weeks ago

Great stay, really loved the hot tub. Loved the privacy and the signs put up to find the cabin were very convenient!

Guest favorite

Apartment in Louisville

4.83 out of 5 average rating, 126 reviews

Highlands Harmony House - Near Cherokee Park

PennyRating, 5 stars1 week ago

The house was very nice and clean in quite neighborhood. The bedding was very comfortable. It was more comfortable than staying at a hotel. And our hostess (Deanna) was very friendly and helpful.

Guest favorite

Farm stay in Simpsonville

4.91 out of 5 average rating, 64 reviews

Spacious Home with Beautiful Views

RitaRating, 5 stars1 month ago

We had a great time! Our first impression was "so pleased" & that describes our stay. Loved the peace & quiet, but we were so close to places we wanted to visit. Very clean. Plenty of seating. We had family over for a meal. Impressed with the amount & variety of spices, etc. that were provided. Having the use of the garage was a bonus. We did fine with Wi-Fi & TV streaming which for us was a miracle! It was a wonderful homecoming & we look forward to a return visit.

Guest favorite

Home in Kentucky

4.9 out of 5 average rating, 111 reviews

The Stagg House on the Ky River

ChristopherRating, 5 stars3 weeks ago

Myself and three friends stayed at the Stagg House during our visit to the bourbon trail. Private and peaceful location along the Kentucky river. Perfect place to stay during our visit to the area.

Guest favorite

Home in Jeffersonville

5 out of 5 average rating, 9 reviews

Amazing 2 units house mins to Louisville!

RobertRating, 5 stars1 week ago

Renee’s place was excellent. She was very communicative from the beginning, helpful in giving some recommendations. The place is easy to get to with a great location. It was very quiet. I was with 4 other parents for our kids volleyball tournament and I would definitely stay here again. Thank you Renee for the hospitality.

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Vacation rentals in Simpsonville

Top-rated vacation rentals in Simpsonville

Sweet Southern Comfort 3 Qn bd 2+bth sleeps 6

Eastern Sky

Historic Nulu Loft| Downtown | Bourbon Trail

Ol Susannah of the Bourbon Trail

2King beds+HotTub+FirePit

Mia's House

The Maple Den

Bourbon Barrel Cottages #4 on the Kentucky Bourbon Trail

Beachfront River Cottage

Eire Cottage Hot Tub & Private Waterfall Luxury

Bourbon Trail Beauty

Top of the Rock

Vacation rentals for every style

Popular amenities for Simpsonville vacation rentals

Stay near Simpsonville's top sights

Other great vacation rentals in Simpsonville

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