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Waddy Vacation Rentals

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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 rentals

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 ￥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 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 ￥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.

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 ￥21,568
￥47,484 total
includes taxes & fees
Oct 27 - Oct 28
Beautiful New 2-Bedroom Villa with Stunning Rolling-Hill Views
A wooden deck with rocking chairs and a bench, surrounded by trees with autumn foliage.

4. On-Site Tastings, 32 Acre Estate, Shuffleboard , 20 minutes to Buffalo Trace

On-Site Tastings, 32 Acre Estate, Shuffleboard , 20 minutes to Buffalo Trace
Waddy
9.0 out of 10, Wonderful, (7 reviews)
"Some friends and I were in town for a bourbon tour and a Keeneland visit. The property is gorgeous, and centrally located between Lexington and Louisville, The house is immaculate and perfect for a trip like this. The host is excellent, and every detail of the property was thought of. Our stay was over and above anything we imagined. Thank You!! "
United States
Timothy S.
The price is ￥40,932
￥129,138 total
includes taxes & fees
Oct 4 - Oct 5
On-Site Tastings, 32 Acre Estate, Shuffleboard , 20 minutes to Buffalo Trace
A log cabin with a stone chimney, multiple windows, and a porch with outdoor seating.

5. Luxury lodge in the heart of the Bluegrass

Luxury lodge in the heart of the Bluegrass
Waddy
10.0 out of 10, Exceptional, (9 reviews)
"Great property, nice location, well appointed. It is close to the interstate and with the leaves off, truck traffic could be heard from the top floor master bed. We would stay here again."
United States
Anonymous traveler
The price is ￥196,713
￥329,113 total
includes taxes & fees
Oct 28 - Oct 29
Luxury lodge in the heart of the Bluegrass
A living room with a sofa, a coffee table, a rug, and a bookshelf.

6. Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.

Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.
Frankfort
8.8 out of 10, Excellent, (110 reviews)
"Perfect location for the Bourbon Trail. Nice, clean, and affordable. 10 out of 10, would do it again!"
United States
Dwight K.
The price is ￥11,016
￥25,922 total
includes taxes & fees
Oct 5 - Oct 6
Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.
A modern living room with a TV mounted on the wall, a wooden console table, a floor lamp, a potted plant, and a basket.

7. Capital City Condo #1 close to Interstate, Water Park, Restaurants and Shopping

Capital City Condo #1 close to Interstate, Water Park, Restaurants and Shopping
Frankfort
8.8 out of 10, Excellent, (92 reviews)
"It was a nice stay"
United States
Teresa M.
The price is ￥11,016
￥25,922 total
includes taxes & fees
Oct 5 - Oct 6
Capital City Condo #1 close to Interstate, Water Park, Restaurants and Shopping
A bar area with a black bar counter, stools, and a large horseshoe-shaped metal object on the wall.

8. Unique Downtown Studio with an Industrial Vibe

Unique Downtown Studio with an Industrial Vibe
Shelbyville
10.0 out of 10, Exceptional, (32 reviews)
"Wonderful location in a very nice small town. Grocery store, coffee shop and many other amenities close by.The property was very spacious and well done for 2 people."
United States
Kathleen S.
The price is ￥14,163
￥27,958 total
includes taxes & fees
Oct 4 - Oct 5
Unique Downtown Studio with an Industrial Vibe
A living room with a TV, a wooden entertainment unit, a round coffee table, and a sofa.

9. Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
Shelbyville
10.0 out of 10, Exceptional, (21 reviews)
"The Stables suite was perfect for an extended stay in Shelbyville. Great location and wonderful place to stay. "
United States
Kim K.
The price is ￥14,950
￥29,006 total
includes taxes & fees
Oct 4 - Oct 5
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
A beige sofa with patterned cushions, a dark patterned rug, and a window with blinds.

10. Capital City Condo #8

Capital City Condo #8
Frankfort
8.6 out of 10, Excellent, (43 reviews)
"This was our third time staying at this place for a bourbon trip. Overall it is a good value, has the basics and close to distilleries. "
United States
Robert V.
The price is ￥11,016
￥25,922 total
includes taxes & fees
Oct 5 - Oct 6
Capital City Condo #8
A reception area with a mounted TV displaying various streaming services, a wooden console with a welcome sign, and a seating area with a table and chairs.

11. Capital City Condo #10

Capital City Condo #10
Frankfort
8.2 out of 10, Very good, (10 reviews)
"Such a great little place. Hosts are wonderful!"
United States
Amanda L.
The price is ￥11,016
￥25,922 total
includes taxes & fees
Oct 14 - Oct 15
Capital City Condo #10
A modern living room with a sofa, a coffee table, and a bed.

12. The Bourbon Garage- walking distance to Buffalo Trace!

The Bourbon Garage- walking distance to Buffalo Trace!
Frankfort
9.8 out of 10, Exceptional, (34 reviews)
"Great property and wonderful hosts! "
United States
Jacinda C.
The price is ￥16,429
￥39,698 total
includes taxes & fees
Oct 26 - Oct 27
The Bourbon Garage- walking distance to Buffalo Trace!
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
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 living room with a large sofa, a coffee table, and a TV. There is a fireplace with a large painting above it.

14. Southern Charm and Comfort on the Bourbon Trail- Trail Suites Inn, Suite C

Southern Charm and Comfort on the Bourbon Trail- Trail Suites Inn, Suite C
Lawrenceburg
10.0 out of 10, Exceptional, (12 reviews)
"Absolutely beautiful well maintained it’s right downtown A+++++ "
United States
Dustin
The price is ￥16,288
￥41,552 total
includes taxes & fees
Oct 5 - Oct 6
Southern Charm and Comfort on the Bourbon Trail- Trail Suites Inn, Suite C
A spacious living area with a high ceiling, a staircase leading to an upper level, a blue sofa, a wooden coffee table, and a TV mounted on the wall.

15. 1BD Modern Bourbon Cottage

1BD Modern Bourbon Cottage
Lawrenceburg
9.6 out of 10, Exceptional, (8 reviews)
"It was absolutely beautiful and such a wonderful place for a little get away! We will definitely we back!"
United States
Maddy W.
The price is ￥21,725
￥50,503 total
includes taxes & fees
Nov 1 - Nov 2
1BD Modern Bourbon Cottage
A modern kitchen with a central island, wooden accents, and a dining area with a table and chairs.

16. 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 living room with a television, leather sofas, a coffee table, and a fireplace.

17. 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 5 - Oct 6
Peaceful Retreat on the Bourbon Trail
A modern living room with a round coffee table, a sofa with numbered cushions, a dining area with striped curtains, and a chandelier with red flowers.

18. Off to the Races Retreat - Hidden Clues Inside

Off to the Races Retreat - Hidden Clues Inside
Frankfort
10.0 out of 10, Exceptional, (11 reviews)
"Great place! "
United States
Brad S.
The price is ￥19,679
￥36,677 total
includes taxes & fees
Nov 1 - Nov 2
Off to the Races Retreat - Hidden Clues Inside
A wooden sign with "Capital City Cottage" written on it, placed in front of a white picket fence.

19. Capital City Cottage

Capital City Cottage
Frankfort
8.6 out of 10, Excellent, (52 reviews)
"Nice little place close to many things, enjoyed our stay "
United States
Tim W.
The price is ￥15,737
￥38,329 total
includes taxes & fees
Oct 14 - Oct 15
Capital City Cottage
A two-story house with a porch, a small garden, and a sign that reads "Hotel."

20. 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
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 10 hours ago
Best Western Parkside Inn

Find out more about Waddy

Search for holiday rentals in Waddy on Expedia! You can easily find your home rentals, villas, holiday apartments in Waddy using one of the methods below:

  • View our selection of featured holiday rentals in Waddy
  • Use the map to find apartments and other holiday homes in the Waddy neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Waddy while they last

Look no further and take a look at our great range of rental properties in Waddy!

Frequently asked questions

Can I find vacation rentals in Waddy?

Yes, you can find vacation rentals close to well known local attractions in Waddy, or you can choose a more remote option if you're looking for a relaxing stay.

What are some of the best vacation home rentals that Waddy has to offer?

Bourbon Trail Estate - Theater, Games & Hot Tub: Visitors like this Waddy vacation home rental. It is located on a river and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Waddy?

With 8 Expedia vacation rentals, you're sure to find just the right place for your Waddy stay.

What can I see and do in Waddy?

While exploring the area, visit family-friendly sights like Blue Grass Railroad Museum, or get outside and enjoy nature at Taylorsville Lake State Park. In the larger area, you’ll find Bulleit Distilling Co. and Berry Hill Mansion.

What are vacation rentals like in Waddy?

Vacation rentals are privately owned accommodations you can stay in for a couple days or more in Waddy. Vacation rentals feature amenities like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for small groups.