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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Waddy vacation homes

A modern kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a marble countertop.

1. Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views

Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views
Waddy
9.0 out of 10, Wonderful, (12 reviews)
"Excellent stay and a beautiful property. Perfect for our needs no complaints."
United States
Anthony T.
The price is ￥19,836
￥59,244 total
includes taxes & fees
Oct 26 - Oct 27
Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views
A modern kitchen with stainless steel appliances, white cabinetry, and a blue accent wall.

2. Beautiful New 2-Bedroom Villa with Stunning Rolling-Hill Views

Beautiful New 2-Bedroom Villa with Stunning Rolling-Hill Views
Waddy
The price is ￥21,568
￥47,484 total
includes taxes & fees
Oct 27 - Oct 28
Beautiful New 2-Bedroom Villa with Stunning Rolling-Hill Views
A modern kitchen with a central island, stainless steel appliances, and a large window providing natural light.

3. Ridge View Villa #1 -Haven in the Heart of the Bourbon Trail.

Ridge View Villa #1 -Haven in the Heart of the Bourbon Trail.
Waddy
10.0 out of 10, Exceptional, (2 reviews)
"The place was great. Tucked away off the main highway and between bourbon country’s best. Well stocked amenities and little things provided that were a great touch. Will be back again!"
United States
Daniel H.
The price is ￥18,727
￥43,263 total
includes taxes & fees
Oct 4 - Oct 5
Ridge View Villa #1 -Haven in the Heart of the Bourbon Trail.
A wooden coffee table with three bottles and a glass container in a living room.

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

This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.
Frankfort
8.8 out of 10, Excellent, (76 reviews)
"Great stay! "
United States
Armando G.
The price is ￥9,446
￥24,958 total
includes taxes & fees
Oct 26 - Oct 27
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.
A modern kitchen with a dining area, built-in shelves, and a green sofa in the living room.

5. Quiet Downtown Maple Cottage Gem

Quiet Downtown Maple Cottage Gem
Shelbyville
10.0 out of 10, Exceptional, (1 review)
"Very convenient for Horse Show we were attending. Everything was as described and the hosts were very accommodating. "
United States
Marlena J.
The price is ￥19,836
￥55,239 total
includes taxes & fees
Oct 5 - Oct 6
Quiet Downtown Maple Cottage Gem
A living room with a fireplace, a television, and a large window.

6. "Deer Creek Lodge" - Secluded Bourbon Trail Stay

"Deer Creek Lodge" - Secluded Bourbon Trail Stay
Lawrenceburg
10.0 out of 10, Exceptional, (4 reviews)
"We had a great experience staying at the Deer Creek Lodge. The location is very peaceful, the lodge was unique and a perfect size, and the hosts were very helpful. We will be back!"
United States
David B.
The price is ￥13,685
￥38,853 total
includes taxes & fees
Oct 14 - Oct 15
"Deer Creek Lodge" - Secluded Bourbon Trail Stay
A kitchen counter with a coffee maker, a coffee filter container, and a sugar and tea container.

7. University Stay | Sleeps 10 | Game Room + Firepit + Grill

University Stay | Sleeps 10 | Game Room + Firepit + Grill
Frankfort
The price is ￥19,375
￥52,794 total
includes taxes & fees
Oct 19 - Oct 20
University Stay | Sleeps 10 | Game Room + Firepit + Grill
A house with a covered porch, outdoor seating, and a grill area.

8. Your Kentucky Bourbon Trail stay hosted by Sixteen Chairs with panoramic horse country views, barrel sauna, cold plunge, hot tub, gym, game room, theatre room, and dedicated outdoor space

Your Kentucky Bourbon Trail stay hosted by Sixteen Chairs with panoramic horse country views, barrel sauna, cold plunge, hot tub, gym, game room, theatre room, and dedicated outdoor space
Shelbyville
The price is ￥26,832
￥118,912 total
includes taxes & fees
Oct 4 - Oct 5
Your Kentucky Bourbon Trail stay hosted by Sixteen Chairs with panoramic horse country views, barrel sauna, cold plunge, hot tub, gym, game room, theatre room, and dedicated outdoor space
A room with a large open door leading to a balcony with a view of houses. There is a small table and chairs on the balcony.

9. This gem sits in the heart of picturesque South Frankfort, near the Kentucky river

This gem sits in the heart of picturesque South Frankfort, near the Kentucky river
Frankfort
8.6 out of 10, Excellent, (12 reviews)
"We had the best time! Second time staying at this location - first time was on the first floor. A great location and very welcoming! We'll be back!"
United States
Melissa R.
The price is ￥16,373
￥33,413 total
includes taxes & fees
Oct 12 - Oct 13
This gem sits in the heart of picturesque South Frankfort, near the Kentucky river
A modern kitchen with a central island, dark wooden stools, a hanging light fixture, and a sliding barn door.

10. "The Homestead" UPSCALE STAY - Downtown with Yard

"The Homestead" UPSCALE STAY - Downtown with Yard
Lawrenceburg
8.8 out of 10, Excellent, (8 reviews)
"We enjoyed being close to distilleries and the small town feel. Several good restaurants nearby. "
United States
Wanda N.
"The Homestead" UPSCALE STAY - Downtown with Yard
A living room with a television, leather sofas, a coffee table, and a fireplace.

11. Peaceful Retreat on the Bourbon Trail

Peaceful Retreat on the Bourbon Trail
Lawrenceburg
10.0 out of 10, Exceptional, (29 reviews)
"Great stay. Would book again easily. "
United States
CODY C.
The price is ￥21,410
￥41,652 total
includes taxes & fees
Oct 6 - Oct 7
Peaceful Retreat on the Bourbon Trail
A modern kitchen with a central island, wooden accents, and a dining area with a table and chairs.

12. Bourbon and Horse Racing

Bourbon and Horse Racing
Frankfort
9.8 out of 10, Exceptional, (52 reviews)
"Beautifully renovated and has everything you need. Would stay here again if we return to the area."
United States
Nancy C.
The price is ￥24,786
￥51,852 total
includes taxes & fees
Oct 14 - Oct 15
Bourbon and Horse Racing
A two-story house with a porch, a small garden, and a sign that reads "Hotel."

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

Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
Shelbyville
9.4 out of 10, Exceptional, (50 reviews)
"Great house and location. Enjoyed our stay. Would use this location again."
United States
Donald A.
The price is ￥24,402
￥45,732 total
includes taxes & fees
Oct 25 - Oct 26
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
A hot tub with a wooden deck, outdoor seating, and string lights.

14. Secluded Bourbon Trail Retreat • Hot Tub, Barrel Sauna, Fire Pit, Game Room

Secluded Bourbon Trail Retreat • Hot Tub, Barrel Sauna, Fire Pit, Game Room
Lawrenceburg
10.0 out of 10, Exceptional, (6 reviews)
"Cozy home with everything you need. Nicely decorated and thoughtful touches throughout home."
United States
Christina A.
The price is ￥21,415
￥75,999 total
includes taxes & fees
Oct 5 - Oct 6
Secluded Bourbon Trail Retreat • Hot Tub, Barrel Sauna, Fire Pit, Game Room
A modern kitchen with white cabinetry, stainless steel appliances, and a granite countertop.

15. the bourbon barrel escape HotTub Game Room pets ok

the bourbon barrel escape HotTub Game Room pets ok
Shelbyville
The price is ￥40,948
￥87,277 total
includes taxes & fees
Oct 19 - Oct 20
the bourbon barrel escape HotTub Game Room pets ok
A living room with a leather sofa, a green armchair, a fireplace, and a chandelier.

16. Award-winning 3 king bedroom retreat in historic downtown Lawrenceburg, steps from Main Street and minutes to the Kentucky Bourbon Trail.

Award-winning 3 king bedroom retreat in historic downtown Lawrenceburg, steps from Main Street and minutes to the Kentucky Bourbon Trail.
Lawrenceburg
9.8 out of 10, Exceptional, (12 reviews)
"Great place to stay for bourbon and Keenland"
United States
Tad S.
The price is ￥24,474
￥64,421 total
includes taxes & fees
Oct 5 - Oct 6
Award-winning 3 king bedroom retreat in historic downtown Lawrenceburg, steps from Main Street and minutes to the Kentucky Bourbon Trail.
A modern kitchen with a large island, wooden beams, recessed lighting, and a view of the living area.

17. Modern Cottage on the Bourbon Trail

Modern Cottage on the Bourbon Trail
Lawrenceburg
10.0 out of 10, Exceptional, (15 reviews)
"Really nice little cottage. We had a great stay!"
United States
Jeff W.
The price is ￥21,402
￥50,482 total
includes taxes & fees
Oct 26 - Oct 27
Modern Cottage on the Bourbon Trail
A large, multi-story house with a central driveway and a pond in the background.

18. Bourbon Trail Lakehouse

Bourbon Trail Lakehouse
Frankfort
9.6 out of 10, Exceptional, (64 reviews)
"Great place to stay!"
United States
Jeff S.
The price is ￥19,498
￥48,747 total
includes taxes & fees
Oct 20 - Oct 21
Bourbon Trail Lakehouse
A two-story house with a wooden deck and a covered porch.

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

This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.
Frankfort
8.0 out of 10, Very good, (49 reviews)
"Affordable place to stay while visiting the bourbon trail. Parking is tight for mid size suv. Absolutely 1 parking spot available. The reminaing parking spot is for the other VRBO. Host is very responsive."
United States
joshua t.
The price is ￥13,219
￥28,910 total
includes taxes & fees
Oct 26 - Oct 27
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.
A compact kitchen with a refrigerator, stove, microwave, and coffee maker. There is a dining area with chairs and a table.

20. Miss Reba's Love is a charming house with a warm Kentucky feel.

Miss Reba's Love is a charming house with a warm Kentucky feel.
Frankfort
10.0 out of 10, Exceptional, (10 reviews)
"Very clean and communication with host was excellent. Would recommend to anyone. "
United States
Chuck F.
The price is ￥25,069
￥51,159 total
includes taxes & fees
Oct 7 - Oct 8
Miss Reba's Love is a charming house with a warm Kentucky feel.
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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Top Waddy Hotel Reviews

Best Western Parkside Inn

Best Western Parkside Inn

10/10 Excellent
"Free coffee all day long"
Arlene 1-night trip
Posted 9 hours ago
Best Western Parkside Inn

Find out more about Waddy

Waddy Vacation Homes information

Number of reviews
353
Accommodation
264 Vacation Homes
Lowest Price
￥24,958
Highest Price
￥118,912