Waddy Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Waddy holiday 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 AU$369
includes taxes & fees
10 Nov - 11 Nov
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 AU$585
includes taxes & fees
11 Nov - 12 Nov
Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views
A kitchen with a central island, wooden ceiling, and bar stools.

3. 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 AU$1,100
includes taxes & fees
10 Nov - 11 Nov
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.

4. 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 traveller
The price is AU$1,920
includes taxes & fees
10 Nov - 11 Nov
Luxury lodge in the heart of the Bluegrass
A modern kitchen with a central island, stainless steel appliances, and bar stools.

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

Beautiful New 2-Bedroom Villa with Stunning Rolling-Hill Views
Waddy
The price is AU$455
includes taxes & fees
9 Dec - 10 Dec
Beautiful New 2-Bedroom Villa with Stunning Rolling-Hill Views
A cozy cabin interior with a stone fireplace, a leather sofa, and a large window offering a view of the outdoors.

6. Cabin+Bunkhouse Sleeps 23 near Lex Lou Like New Spacious Modern Rustic Retreat

Cabin+Bunkhouse Sleeps 23 near Lex Lou Like New Spacious Modern Rustic Retreat
Shelbyville
10.0 out of 10, Exceptional, (13 reviews)
"Nice stay"
United States
Jackie S.
The price is AU$2,357
includes taxes & fees
7 Dec - 8 Dec
Cabin+Bunkhouse Sleeps 23 near Lex Lou Like New Spacious Modern Rustic Retreat
A spacious living room with two grey sofas, a wooden bookshelf, and a staircase leading to an upper level.

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

H-DERBY, Keeneland, Bourbon or Family Gathering!
Frankfort
9.8 out of 10, Exceptional, (88 reviews)
"Another great trip to the Bourbon Trail with the guys. Great house in a perfect location."
United States
Jason M.
The price is AU$1,001
includes taxes & fees
10 Nov - 11 Nov
H-DERBY, Keeneland, Bourbon or Family Gathering!
A swimming pool with a deck area, outdoor seating, and a covered patio with string lights.

8. *NEW* UNIQUE HOME: HOT TUB-SAUNA-FIREPIT-GAME ROOM-SPEAKEASY-INGROUND POOL-6 BEDS/5 BATHS-5 KING BEDS

*NEW* UNIQUE HOME: HOT TUB-SAUNA-FIREPIT-GAME ROOM-SPEAKEASY-INGROUND POOL-6 BEDS/5 BATHS-5 KING BEDS
Bagdad
9.8 out of 10, Exceptional, (11 reviews)
"My family & I had a great time at the house. My grandkids loved the pool. It was a very enjoyable stay."
United States
LORI T.
*NEW* UNIQUE HOME: HOT TUB-SAUNA-FIREPIT-GAME ROOM-SPEAKEASY-INGROUND POOL-6 BEDS/5 BATHS-5 KING BEDS
A gazebo with a stone base and metal roof, surrounded by a wooden fence and trees.

9. Bourbon Trail Cabin on the Farm

Bourbon Trail Cabin on the Farm
Lawrenceburg
10.0 out of 10, Exceptional, (65 reviews)
"The cabin and grounds were perfectly relaxing-we hope to return!"
United States
Julie N.
The price is AU$276
includes taxes & fees
15 Nov - 16 Nov
Bourbon Trail Cabin on the Farm
An outdoor deck with a long table set for dining, surrounded by chairs, and a view of a red building in the distance.

10. 6 Private Acres! HotTub~Theater | Gamerm | Arcade

6 Private Acres! HotTub~Theater | Gamerm | Arcade
Frankfort
10.0 out of 10, Exceptional, (3 reviews)
"The host and property were excellent! Well equipped, great location, lots for everyone of all ages to relax. Quick drive over to Keeneland and other horse and bourbon country fun as well."
United States
John H.
The price is AU$1,167
includes taxes & fees
10 Nov - 11 Nov
6 Private Acres! HotTub~Theater | Gamerm | Arcade
A modern kitchen with a central island, wooden accents, and a dining area with a table and chairs.

11. Bourbon and Horse Racing

Bourbon and Horse Racing
Frankfort
9.8 out of 10, Exceptional, (55 reviews)
"Beautifully renovated and has everything you need. Would stay here again if we return to the area."
United States
Nancy C.
Bourbon and Horse Racing
A log cabin with a covered porch, large windows, and a well-maintained front yard.

12. The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade Barn, Sleeps 12+

The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade Barn, Sleeps 12+
Shelbyville
10.0 out of 10, Exceptional, (12 reviews)
"Stay was great, the place was perfect, and the view was beautiful."
United States
Bobby E.
The price is AU$859
includes taxes & fees
10 Nov - 11 Nov
The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade Barn, Sleeps 12+
A wooden sauna structure with a door open, a pool, and lounge chairs in the background.

13. Pool Hot Tub Sauna Fire Pit Game & Theater Room

Pool Hot Tub Sauna Fire Pit Game & Theater Room
Frankfort
The price is AU$1,310
includes taxes & fees
10 Nov - 11 Nov
Pool Hot Tub Sauna Fire Pit Game & Theater Room
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and pendant lighting.

14. 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, (29 reviews)
"Beautiful and spacious! The host has thought of absolutely everything. We had a wonderfully relaxing time and the beds are SUPER comfortable! It's a perfect blend of being "out in the country" and close enough to civilization that you don't feel isolated."
United States
Sabrina P.
The price is AU$683
includes taxes & fees
10 Nov - 11 Nov
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill
A kitchen with grey cabinets, a large island, pendant lighting, and a view of the outdoors.

15. Beautiful restored Victorian farmhouse

Beautiful restored Victorian farmhouse
Shelbyville
9.4 out of 10, Exceptional, (16 reviews)
"Lovely place, great outdoor seating areas, and spacious rooms."
United States
Joann E.
The price is AU$609
includes taxes & fees
10 Nov - 11 Nov
Beautiful restored Victorian farmhouse
A beige sofa with patterned cushions, a dark patterned rug, and a window with blinds.

16. 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 AU$228
includes taxes & fees
10 Nov - 11 Nov
Capital City Condo #8
A modern living room with a TV mounted on the wall, a wooden console table, a floor lamp, a potted plant, and a basket.

17. 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 AU$228
includes taxes & fees
10 Nov - 11 Nov
Capital City Condo #1 close to Interstate, Water Park, Restaurants and Shopping
A bar area with stools, a coffee machine, and a large metal horseshoe decoration on the wall.

18. Unique Downtown Studio with an Industrial Vibe

Unique Downtown Studio with an Industrial Vibe
Shelbyville
10.0 out of 10, Exceptional, (34 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 AU$249
includes taxes & fees
8 Dec - 9 Dec
Unique Downtown Studio with an Industrial Vibe
A bed with a wooden headboard and patterned bedding.

19. Capital City Condo #5 Close to Water Park and Restaurants

Capital City Condo #5 Close to Water Park and Restaurants
Frankfort
8.6 out of 10, Excellent, (27 reviews)
"Quiet, affordable, nice local get away. Would book again."
United States
SANDRA
The price is AU$228
includes taxes & fees
10 Nov - 11 Nov
Capital City Condo #5 Close to Water Park and Restaurants
A covered outdoor patio with wicker furniture, a fire pit, and string lights.

20. Kentucky Bourbon Trail: Hot Tub & Game Room

Kentucky Bourbon Trail: Hot Tub & Game Room
Bagdad
10.0 out of 10, Exceptional, (26 reviews)
"Such a beautiful, peaceful area and the cutest home! It was perfect for our large group and Iris was an incredible host. We definitely want to visit again!"
United States
Hannah G.
The price is AU$799
includes taxes & fees
10 Nov - 11 Nov
Kentucky Bourbon Trail: Hot Tub & 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

A hotel sign for Candlewood Suites, an IHG hotel, with a modern building in the background and parked cars in front.
Candlewood Suites Shelbyville by IHG

Candlewood Suites Shelbyville by IHG

Candlewood Suites Shelbyville by IHG
Shelbyville

10/10 Excellent

Room was so clean and staff was so friendly esp Ash.
Australia
Mateo
Reviewed November 26, 2025
Candlewood Suites Shelbyville by IHG

Find out more about Waddy

Everything you need to know about Waddy holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Waddy holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Waddy holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Waddy holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Waddy. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Waddy holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Waddy holiday rentals we have selected for you start as low as AU$218 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Waddy rentals

At Expedia, we put the best Waddy holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Waddy rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Waddy holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Waddy. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find holiday rentals in Waddy?

Yes, there are holiday rentals close to the most popular sights in Waddy, or you can select a more secluded option if you're looking for a relaxing stay.

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

Bourbon Trail Estate - Theater, Games & Hot Tub: This highly rated holiday home rental in Waddy is located on a river, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Waddy?

With 8 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Bulleit Distilling Co. and Berry Hill Mansion.

What are holiday rentals like in Waddy?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Waddy. Holiday rentals offer amenities like laundry facilities and kitchens so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for a small group gathering.