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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

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 CA $112
CA $438 total
includes taxes & fees
Sep 13 - Sep 14
Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views
A modern kitchen with a central island, stainless steel appliances, and a large window providing natural light.

2. 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 CA $164
CA $386 total
includes taxes & fees
Sep 21 - Sep 22
Ridge View Villa #1 -Haven in the Heart of the Bourbon Trail.
A house with a covered porch, outdoor seating, and a grill area.

3. Your Kentucky Bourbon Trail stay 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 with panoramic horse country views, barrel sauna, cold plunge, hot tub, gym, game room, theatre room, and dedicated outdoor space
Shelbyville
The price is CA $235
CA $985 total
includes taxes & fees
Sep 13 - Sep 14
Your Kentucky Bourbon Trail stay with panoramic horse country views, barrel sauna, cold plunge, hot tub, gym, game room, theatre room, and dedicated outdoor space
A modern kitchen with a central island, wooden accents, and a dining area with a table and chairs.

4. Bourbon and Horse Racing

Bourbon and Horse Racing
Frankfort
10.0 out of 10, Exceptional, (51 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 CA $217
CA $461 total
includes taxes & fees
Sep 14 - Sep 15
Bourbon and Horse Racing
A living room with a television, leather sofas, a coffee table, and a fireplace.

5. Peaceful Retreat on the Bourbon Trail

Peaceful Retreat on the Bourbon Trail
Lawrenceburg
10.0 out of 10, Exceptional, (28 reviews)
"Great stay. Would book again easily. "
United States
CODY C.
The price is CA $176
CA $352 total
includes taxes & fees
Sep 21 - Sep 22
Peaceful Retreat on the Bourbon Trail
A modern kitchen with a dining area, built-in shelves, and a green sofa in the living room.

6. 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 CA $174
CA $484 total
includes taxes & fees
Sep 29 - Sep 30
Quiet Downtown Maple Cottage Gem
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and pendant lighting.

7. Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill

Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill
Frankfort
9.8 out of 10, Exceptional, (27 reviews)
"Our stay was amazing! Beautiful porch for sitting outside on a rainy Kentucky night in late spring. The spa was delightful as well when it was raining. We stayed with our daughter and son in law, we look forward to bringing friends with us in the future."
United States
Laura O.
The price is CA $246
CA $677 total
includes taxes & fees
Sep 14 - Sep 15
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill
A hot tub with a wooden deck and stairs, surrounded by a grassy area and trees.

8. Bourbon Trail Getaway | Hot Tub • Fire Pit

Bourbon Trail Getaway | Hot Tub • Fire Pit
Lawrenceburg
10.0 out of 10, Exceptional, (30 reviews)
"The house was great, very clean, owners communicated great, check in was easy, highly recommend the house! "
United States
Ron C.
The price is CA $275
CA $764 total
includes taxes & fees
Sep 15 - Sep 16
Bourbon Trail Getaway | Hot Tub • Fire Pit
A modern kitchen with a central island, dark wooden stools, a hanging light fixture, and a sliding barn door.

9. "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 price is CA $142
CA $352 total
includes taxes & fees
Sep 16 - Sep 17
"The Homestead" UPSCALE STAY - Downtown with Yard
A hot tub with a wooden deck, outdoor seating, and string lights.

10. 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 CA $188
CA $671 total
includes taxes & fees
Sep 14 - Sep 15
Secluded Bourbon Trail Retreat • Hot Tub, Barrel Sauna, Fire Pit, Game Room
A two-story house with a porch, a small garden, and a sign that reads "Hotel."

11. 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, (48 reviews)
"Great house and location. Enjoyed our stay. Would use this location again."
United States
Donald A.
The price is CA $217
CA $426 total
includes taxes & fees
Sep 14 - Sep 15
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
A compact kitchen with a refrigerator, stove, microwave, and coffee maker. There is a dining area with chairs and a table.

12. 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 CA $220
CA $454 total
includes taxes & fees
Sep 21 - Sep 22
Miss Reba's Love is a charming house with a warm Kentucky feel.
A wooden coffee table with three bottles and a glass container in a living room.

13. 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
9.0 out of 10, Wonderful, (75 reviews)
"Parking was great. We were able to walk right into the cute town of Frankfort. The bathroom is quite small and slightly outdated. Other than that, Bourbon On The Hill was perfect for girls weekend! "
United States
Megan E.
The price is CA $83
CA $219 total
includes taxes & fees
Sep 14 - Sep 15
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.
A modern kitchen with a large island, wooden beams, recessed lighting, and a view of the living area.

14. Modern Cottage on the Bourbon Trail

Modern Cottage on the Bourbon Trail
Lawrenceburg
10.0 out of 10, Exceptional, (14 reviews)
"Really nice little cottage. We had a great stay!"
United States
Jeff W.
The price is CA $152
CA $399 total
includes taxes & fees
Sep 29 - Sep 30
Modern Cottage on the Bourbon Trail
A patio with a table and chairs, a barbecue grill, and a covered umbrella.

15. the bourbon barrel escape HotTub Game Room pets ok

the bourbon barrel escape HotTub Game Room pets ok
Shelbyville
The price is CA $359
CA $807 total
includes taxes & fees
Sep 28 - Sep 29
the bourbon barrel escape HotTub Game Room pets ok
A log cabin interior with a ceiling fan, large windows, and four seating areas.

16. Bourbon Trail Cabin-Sleeps 10-Hot Tub, Firepit by Iconiq Stays

Bourbon Trail Cabin-Sleeps 10-Hot Tub, Firepit by Iconiq Stays
LAWRENCEBURG
10.0 out of 10, Exceptional, (21 reviews)
"Awesome place to stay, our family enjoyed the stay!"
United States
Kevin I.
The price is CA $210
CA $674 total
includes taxes & fees
Sep 15 - Sep 16
Bourbon Trail Cabin-Sleeps 10-Hot Tub, Firepit by Iconiq Stays
A spacious living room with two grey sofas, a wooden bookshelf, and a staircase leading to an upper level.

17. H-DERBY, Keeneland, Bourbon or Family Gathering!

H-DERBY, Keeneland, Bourbon or Family Gathering!
Frankfort
9.8 out of 10, Exceptional, (81 reviews)
"Another great trip to the Bourbon Trail with the guys. Great house in a perfect location."
United States
Jason M.
The price is CA $559
CA $992 total
includes taxes & fees
Sep 15 - Sep 16
H-DERBY, Keeneland, Bourbon or Family Gathering!
A white building with a porch, columns, and a covered entrance.

18. Luxury farmhouse on Bourbon Trail with hot tub - Bulleit 4 mi - Frankfort 15 mi

Luxury farmhouse on Bourbon Trail with hot tub - Bulleit 4 mi - Frankfort 15 mi
Bagdad
10.0 out of 10, Exceptional, (17 reviews)
"Great location and very clean. Plenty of room to spread out and relax. Carrie is a Professional and thoughtful host!!"
United States
David S.
The price is CA $537
CA $1,078 total
includes taxes & fees
Sep 21 - Sep 22
Luxury farmhouse on Bourbon Trail with hot tub - Bulleit 4 mi - Frankfort 15 mi
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.

19. 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 CA $130
CA $279 total
includes taxes & fees
Sep 13 - Sep 14
This gem sits in the heart of picturesque South Frankfort, near the Kentucky river
A modern living room with a sofa, armchairs, a coffee table, and a fireplace.

20. Stylish Bourbon Trail 3BR Home Walk to State Capitol 2.5 miles to Buffalo Trace

Stylish Bourbon Trail 3BR Home Walk to State Capitol 2.5 miles to Buffalo Trace
Frankfort
10.0 out of 10, Exceptional, (11 reviews)
"Was a great place to get together with family for the weekend. Very nice furnishings throughout the house. "
United States
Michal T.
The price is CA $173
CA $545 total
includes taxes & fees
Sep 29 - Sep 30
Stylish Bourbon Trail 3BR Home Walk to State Capitol 2.5 miles to Buffalo Trace
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

Bluegrass Inn

Bluegrass Inn

10/10 Excellent
"Good room nice comfortable beds, great price. Very good staff 👍"
Daniel 2-night trip
Posted 1 hour ago
Bluegrass Inn

Find out more about Waddy

Waddy Vacation Homes information

Number of reviews
403
Accommodation
258 Vacation Homes
Lowest Price
CA $219
Highest Price
CA $1,078

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