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Compare 336 Vacation Homes in Shelbyville with updated reviews, rates, and availability.

Bourbon Trail Downtown Frankfort w/Game Room near Buffalo Trace

9.6 out of 10, Exceptional, (20)
"The house was fabulous. It was old, big, beautiful and clean; full of character. It was nice to have a pool table, slot machine and an assortment of games to play. The host provided snacks, coffee, water, shampoos & conditioners. Anything you'd need. The house was five minutes from Buffalo Trace and downtown Frankfort. The only downside was the neighborhood. It is very run down, but we felt COMPLETELY SAFE. Side note - Goodwood had great food & cocktails and so did The Stave. "
The price is SAR 581
SAR 1,119 total
includes taxes & fees
19 Feb - 20 Feb
Bourbon Trail Downtown Frankfort w/Game Room near Buffalo Trace

Horse Farm 4-bedroom house with AC and WiFi in Bourbon Country

2.0 star property
10.0 out of 10, Exceptional, (6)
"House was perfect to hub out of for the bourbon tours. Wife loved the horses on the property. "
Horse Farm 4-bedroom house with AC and WiFi in Bourbon Country

"Centrally Located to Many Distilleries" House on the Kentucky Bourbon Trail

9.8 out of 10, Exceptional, (120)
"We had a great time staying here. Communication with the owner was easy. Clean and comfortable house."
"Centrally Located to Many Distilleries" House on the Kentucky Bourbon Trail

Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill

9.8 out of 10, Exceptional, (13)
"My brother and I and our spouses stayed here as a base for exploring bourbon distilleries. The house was perfect for us and was beautifully decorated. I regret not using the hot tub and fire pit but the snow and cold weather was too much to hang out outdoors! "
Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill

Home Sweet Hayden - 4 beds/3 Full Bath in East End

10.0 out of 10, Exceptional, (36)
"This home was exactly what you hoped for when searching for a short, stay location. Reasonably priced, extraordinarily clean, and well furnished."
Home Sweet Hayden - 4 beds/3 Full Bath in East End

Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!

10.0 out of 10, Exceptional, (82)
"We did a two day bourbon trail and this house fit our needs perfectly! Quiet. Safe. Beautiful! Plan to stay again for our next visit. "
The price is SAR 750
SAR 1,899 total
includes taxes & fees
2 Mar - 3 Mar
Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!

Brand New Build > Hot Tub > 3 King Beds > 7 Minutes to Buffalo Trace

10.0 out of 10, Exceptional, (1)
"My husband and I booked a last minute stay to visit Buffalo Trace and a few other bourbon distilleries. We couldn’t have picked a better place. Centrally located to many distilleries and just 7 minutes to Buffalo Trace. The home is sparkling new with all the extra touches. From the plush bath towels, perfect mattress, hot tub with twinkle lights, the coffee bar, and plush oversized sofa that was perfect for watching late night movies. Seriously one of the best VRBO stays in our many travels and...
The price is SAR 563
SAR 1,627 total
includes taxes & fees
17 Feb - 18 Feb
Brand New Build > Hot Tub > 3 King Beds > 7 Minutes to Buffalo Trace

Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby

9.2 out of 10, Wonderful, (13)
"Wonderful warm home. Loved all the personal touchs this place had to offer. Location, parking was the best to take in Shelbyville!"
The price is SAR 315
SAR 747 total
includes taxes & fees
17 Feb - 18 Feb
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby

Hist. Frankfort: Hot Tub, Downtown, Bourbon Trail

10.0 out of 10, Exceptional, (2)
"This was a wonderful stay for us! The location was within walking distance to the Capital building and downtown. Close proximity to several distilleries, groceries, the outlet mall, and Josephine Sculpture park. About thr home: super comfotable, super clean, and super big! Perfect for a friends getaway, a big family, or a couples weekend. THThe fenced in year was a great bunis dor those teaveling woth pets!weeforfamily.fencyearand"
The price is SAR 749
SAR 2,119 total
includes taxes & fees
17 Feb - 18 Feb
Hist. Frankfort: Hot Tub, Downtown, Bourbon Trail

Two Miles to Buffalo Trace > Speakeasy > Hot Tub > Gas Fire Pit

10.0 out of 10, Exceptional, (11)
"Book this place now!! This adorable home is in a prime location for all of your bourbon trail activities. The decor is just as lovely as pictured, and the beds are very comfortable. The hot tub provided a relaxing spot for us girls to unwind, while our hubbies kicked back around the fire pit. We began each morning lazily with coffee around the whiskey room’s gas fireplace. It was divine! "
Two Miles to Buffalo Trace > Speakeasy > Hot Tub > Gas Fire Pit

Lakefront Home Close to Bourbon Trail--Dog friendly and now with WiFi!

9.8 out of 10, Exceptional, (69)
"Wonderful place. "
Lakefront Home Close to Bourbon Trail--Dog friendly and now with WiFi!

KY Bourbon Trail FUN! Double Shot on Main 2 Bed/2 Bath

10.0 out of 10, Exceptional, (87)
"Me and my boyfriend were here celebrating our birthdays and from the moment we walked in, we were impressed! We loved how clean and welcoming the place was. Each room felt like you were stepping into a different unique space, with plenty of different activities to choose from for adults or younger people. We enjoyed how close our destinations were, plus food in the area was amazing. We didn’t need for anything during our stay, there was everything you could think of provided for us for a...
The price is SAR 506
SAR 805 total
includes taxes & fees
18 Feb - 19 Feb
KY Bourbon Trail FUN! Double Shot on Main 2 Bed/2 Bath

This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.

9.2 out of 10, Wonderful, (41)
"Our second stay at this property was as good as the first. Top notch all around. "
The price is SAR 225
SAR 591 total
includes taxes & fees
20 Feb - 21 Feb
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.

Limestone Landing - Cozy Luxury Retreat w/ Hot Tub

10.0 out of 10, Exceptional, (41)
"This house is in a beautiful spot with a stream running through the backyard. In the evenings we would sit in the hot tub and relax in the peaceful surroundings. The layout of the house is great, with plenty of kitchen and livingroom space. The beds are very comfortable. The owner provided everything we needed including lots of towels, laundry and dish soap, miscellaneous toiletries, even some snacks!The location of the house was convenient for the distilleries that we visited: Buffalo Trace,...
Limestone Landing - Cozy Luxury Retreat w/ Hot Tub

1890's charm on Bourbon Trail- 7 distilleries w/in 25min! Bourbon Room in house!

10.0 out of 10, Exceptional, (66)
"Very roomy and cozy. "
1890's charm on Bourbon Trail- 7 distilleries w/in 25min! Bourbon Room in house!

NEW: Hot Tub, Pool, Fully Loaded, 10 min to Bulleit, Between LOU and LEX.

10.0 out of 10, Exceptional, (1)
"Our stay at the Bourbon Bungalow was a fantastic experience for our group of three families! The property is in a peaceful, rural spot across from Guist Creek Lake, offering a relaxing atmosphere and perfect access to the Bourbon Trail.The house is incredibly spacious and thoughtfully designed. Each of the four bedrooms is themed after a local distillery, adding a unique, fun touch. The Woodford and Buffalo Trace rooms, both with king beds and en-suite baths, were hits for the adults. The...
The price is SAR 656
SAR 1,756 total
includes taxes & fees
17 Feb - 18 Feb
NEW: Hot Tub, Pool, Fully Loaded, 10 min to Bulleit, Between LOU and LEX.

Cheerful Historical Mansion 8-bedrooms and 6 baths Vacation Home in Derby City

9.8 out of 10, Exceptional, (63)
"My sorority sisters and I booked this property for a weekend together - we had a lovely time, even though weather caused us to cut the trip short. The host was very responsive and understanding of our leaving ahead of schedule. The property was a great size for our group and we had plenty of space to spread out but still be together. "
The price is SAR 2,247
SAR 4,467 total
includes taxes & fees
17 Feb - 18 Feb
Cheerful Historical Mansion 8-bedrooms and 6 baths Vacation Home in Derby City

New Luxury Brbn Trail w HotTub + GameRoom + Sauna

10.0 out of 10, Exceptional, (53)
"Posting is exactly as the property is and more! This place is perfect for friends and family. Perfect meeting of fun and relaxation. Host was amazing, quick response, accommodating and thoughtful. Quick and easy to many local restaurants and distilleries. 100/100 would recommend and we hope to stay again in the future. Absolutely top notch!"
The price is SAR 2,729
SAR 5,229 total
includes taxes & fees
9 Mar - 10 Mar
New Luxury Brbn Trail w HotTub + GameRoom + Sauna

The Stagg House on the Ky River

10.0 out of 10, Exceptional, (8)
"The cabin was so cute. Lots of room!"
The price is SAR 713
SAR 1,176 total
includes taxes & fees
23 Feb - 24 Feb
The Stagg House on the Ky River

Upscale Kentucky Bourbon Trail & Close to Louisville

10.0 out of 10, Exceptional, (20)
"We all loved the property and had more than enough space for 6 of us to relax after visiting distilleries. Having 2 kitchens and 2 living rooms was perfect when we needed some space or quiet, and there is a good sized tvs in each living room. The bathrooms and kitchens are nicely updated. We walked to dinner in downtown shelbyville - about 4-5 blocks. We would definitely stay there again. "
Upscale Kentucky Bourbon Trail & Close to Louisville
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Shelbyville

Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby

9.2 out of 10, Wonderful, (13)
"Wonderful warm home. Loved all the personal touchs this place had to offer. Location, parking was the best to take in Shelbyville!"
The price is SAR 315
SAR 747 total
includes taxes & fees
17 Feb - 18 Feb
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby

Cabin+Bunkhouse Sleeps 25 near Lou/Lex *Like-New!

10.0 out of 10, Exceptional, (15)
"Great space! Perfect for a handful of folks or a bigger family gathering. Quiet and self-contained environment. And, convenient for the Bourbon Trail, Golf, with easy access to Louisville or Lexington."
The price is SAR 2,063
SAR 4,343 total
includes taxes & fees
17 Feb - 18 Feb
Cabin+Bunkhouse Sleeps 25 near Lou/Lex *Like-New!

2025 KY Derby 30 min Away ~ Bourbon Trail ~ Hot Tub

10.0 out of 10, Exceptional, (19)
"The location is perfect for horse races and distillery tours. With it being located in between Lexington and Louisville, it was perfect for day trips to places of interest. "
2025 KY Derby 30 min Away ~ Bourbon Trail ~ Hot Tub
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.