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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Waddy vacation homes

A modern kitchen with a central island, stainless steel appliances, and a large window providing natural light.

1. 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 AED 437
AED 1,026 total
includes taxes & fees
12 Oct - 13 Oct
Ridge View Villa #1 -Haven in the Heart of the Bourbon Trail.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a marble countertop.

2. 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 AED 338
AED 1,213 total
includes taxes & fees
14 Oct - 15 Oct
Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views
A single-story house with a white exterior, black shutters, and a number 'Two' sign above the door.

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

Beautiful New 2-Bedroom Villa with Stunning Rolling-Hill Views
Waddy
The price is AED 665
AED 1,312 total
includes taxes & fees
3 Nov - 4 Nov
Beautiful New 2-Bedroom Villa with Stunning Rolling-Hill Views
A living room with a fireplace, a television, and a large window.

4. "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 AED 351
AED 946 total
includes taxes & fees
21 Oct - 22 Oct
"Deer Creek Lodge" - Secluded Bourbon Trail Stay
A wooden coffee table with three bottles and a glass container in a living room.

5. 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, (77 reviews)
"Great stay! "
United States
Armando G.
The price is AED 220
AED 582 total
includes taxes & fees
2 Nov - 3 Nov
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.

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 AED 463
AED 1,289 total
includes taxes & fees
12 Oct - 13 Oct
Quiet Downtown Maple Cottage Gem
A house with a covered porch, outdoor seating, and a grill area.

7. 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 AED 949
AED 3,187 total
includes taxes & fees
26 Oct - 27 Oct
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 living room with a television, leather sofas, a coffee table, and a fireplace.

8. Peaceful Retreat on the Bourbon Trail

Peaceful Retreat on the Bourbon Trail
Lawrenceburg
10.0 out of 10, Exceptional, (31 reviews)
"Very nice place."
United States
Josh B.
The price is AED 468
AED 1,039 total
includes taxes & fees
22 Oct - 23 Oct
Peaceful Retreat on the Bourbon Trail
A two-story house with a porch, a small garden, and a sign that reads "Hotel."

9. 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 AED 555
AED 1,100 total
includes taxes & fees
25 Oct - 26 Oct
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
A modern kitchen with a central island, wooden accents, and a dining area with a table and chairs.

10. 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 AED 579
AED 1,219 total
includes taxes & fees
12 Oct - 13 Oct
Bourbon and Horse Racing
A modern kitchen with a central island, dark wooden stools, a hanging light fixture, and a sliding barn door.

11. "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 AED 377
AED 970 total
includes taxes & fees
11 Oct - 12 Oct
"The Homestead" UPSCALE STAY - Downtown with Yard
A modern kitchen with white cabinetry, stainless steel appliances, and a granite countertop.

12. the bourbon barrel escape HotTub Game Room pets ok

the bourbon barrel escape HotTub Game Room pets ok
Shelbyville
The price is AED 955
AED 2,028 total
includes taxes & fees
14 Oct - 15 Oct
the bourbon barrel escape HotTub Game Room pets ok
A hot tub with a wooden deck, outdoor seating, and string lights.

13. 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.
Secluded Bourbon Trail Retreat • Hot Tub, Barrel Sauna, Fire Pit, Game Room
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, (15 reviews)
"Really nice little cottage. We had a great stay!"
United States
Jeff W.
The price is AED 438
AED 1,122 total
includes taxes & fees
27 Oct - 28 Oct
Modern Cottage on the Bourbon Trail
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.

15. 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 AED 345
AED 743 total
includes taxes & fees
2 Nov - 3 Nov
This gem sits in the heart of picturesque South Frankfort, near the Kentucky river
A two-story house with a wooden deck and a covered porch.

16. 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 AED 275
AED 637 total
includes taxes & fees
2 Nov - 3 Nov
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.

17. 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 AED 585
AED 1,194 total
includes taxes & fees
20 Oct - 21 Oct
Miss Reba's Love is a charming house with a warm Kentucky feel.
A kitchen with a large stainless steel sink, wooden countertops, and brick walls.

18. Shire-Southern-Comfort quiet 3-bedroom house w/WiFi and AC in heart of downtown

Shire-Southern-Comfort quiet 3-bedroom house w/WiFi and AC in heart of downtown
Frankfort
9.8 out of 10, Exceptional, (25 reviews)
"This was perfect for our week in Frankfort"
United States
Dan G.
The price is AED 383
AED 982 total
includes taxes & fees
12 Oct - 13 Oct
Shire-Southern-Comfort quiet 3-bedroom house w/WiFi and AC in heart of downtown
A house with a front porch, a wooden bench, a sign indicating a Kentucky Bourbon Trail, and a small garden with plants and rocks.

19. CLEAN! 2 Bed/2 Bath/Game Room

CLEAN! 2 Bed/2 Bath/Game Room
Lawrenceburg
10.0 out of 10, Exceptional, (145 reviews)
"Great hospitality. Great tips for fun stuff to do in the area!"
United States
Kim W.
The price is AED 593
AED 994 total
includes taxes & fees
12 Oct - 13 Oct
CLEAN! 2 Bed/2 Bath/Game Room
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
"Very clean inexpensive stay"
Arthur 1-night trip
Posted 13 hours ago
Bluegrass Inn