Waddy Vacation Rentals

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Our top choices for Waddy vacation rentals

Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views

Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views
Waddy
8.8 out of 10, Excellent, (9)
"Clean, quiet and a great location. "
United States
Marla B.
The price is ¥15,241
¥48,371 total
includes taxes & fees
Dec 15 - Dec 16
Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views

Private 7 Acre Estate 6-Bdrm Home+Putting Green+Theatre+Hot Tub+Game Rm+Fire Pit

Private 7 Acre Estate 6-Bdrm Home+Putting Green+Theatre+Hot Tub+Game Rm+Fire Pit
Frankfort
10.0 out of 10, Exceptional, (2)
"3 couples had a great stay at the property. Very clean and tastefully decorated. Well equipped kitchen-needs a new cork screw-but, we were there for the bourbon. Beautiful setting and in the middle of the distilleries we wanted to visit in Bardstown, Frankfort, Versailles and Lexington. Only negative would be it needed some extra wash cloths for bathrooms and bath mats. "
United States
Elizabeth B.
The price is ¥95,496
¥188,541 total
includes taxes & fees
Dec 15 - Dec 16
Private 7 Acre Estate 6-Bdrm Home+Putting Green+Theatre+Hot Tub+Game Rm+Fire Pit

Luxury lodge in the heart of the Bluegrass

Luxury lodge in the heart of the Bluegrass
Waddy
10.0 out of 10, Exceptional, (8)
"Great location, close to Frankfort, Louisville and Lexington. Theater room was amazing! "
United States
Nicole D.
The price is ¥207,539
¥328,278 total
includes taxes & fees
Dec 15 - Dec 16
Luxury lodge in the heart of the Bluegrass

Bourbon Trail: Caboose on the Farm

Bourbon Trail: Caboose on the Farm
Lawrenceburg
10.0 out of 10, Exceptional, (38)
"Staying in the Caboose on the Farm was such a fun and relaxing escape. The space was clean, cozy and full of charm with beautiful views and friendly animals. It was the perfect mix of comfort and nature. Highly recommend for anyone looking for a unique getaway!"
United States
Lindsey
The price is ¥22,086
¥36,626 total
includes taxes & fees
Dec 15 - Dec 16
Bourbon Trail: Caboose on the Farm

Capital City Condo #2

Capital City Condo #2
Frankfort
9.2 out of 10, Wonderful, (59)
"My husband and I stayed for 4 nights and this condo was a great place to come back to each evening to relax. Easy check in/check out, location was a bit run down but never had any problems or felt unsafe so don't let that discourage you from choosing this place for your stay in Frankfort. "
United States
Carrie D.
The price is ¥10,907
¥25,665 total
includes taxes & fees
Dec 16 - Dec 17
Capital City Condo #2

Capital City Condo #8

Capital City Condo #8
Frankfort
8.6 out of 10, Excellent, (36)
"The condo was good for an overnight stay. The owners were very responsive & kind. Very close to just about anything you want to do. The price was good for the accommodations. Thank you for the hospitality! "
United States
Pollee F.
The price is ¥10,907
¥25,665 total
includes taxes & fees
Dec 15 - Dec 16
Capital City Condo #8

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, (4)
"Cute and comfortable place. I was very impressed and the host, Kyra was very communicative and great to work with! Will definitely be my "go-to" when I'm in the area again. "
United States
Lanita C.
The price is ¥11,359
¥34,854 total
includes taxes & fees
Dec 19 - Dec 20
Southern Charm and Comfort on the Bourbon Trail- Trail Suites Inn, Suite C

Five Minutes from Keeneland!

Five Minutes from Keeneland!
Versailles
10.0 out of 10, Exceptional, (23)
"This wonderful property is in the heart of lovely horse farms. Minutes from the airport, Keeneland Race Track and downtown Lexington. Super easy to find and so warm and welcoming. Just perfect for adventures. "
United States
Heidi D.
The price is ¥28,186
¥50,140 total
includes taxes & fees
Dec 16 - Dec 17
Five Minutes from Keeneland!

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, (68)
"Great stay! "
United States
Armando G.
The price is ¥9,349
¥24,701 total
includes taxes & fees
Dec 17 - Dec 18
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.

Bourbon Barrel Cabin B. There are 2 cabins available A & B. Brand new Cabins.

Bourbon Barrel Cabin B. There are 2 cabins available A & B. Brand new Cabins.
Frankfort
9.8 out of 10, Exceptional, (14)
"Property was clean and comfy! Would stay again. "
United States
Amy L.
The price is ¥23,683
¥41,883 total
includes taxes & fees
Dec 15 - Dec 16
Bourbon Barrel Cabin B. There are 2 cabins available A & B. Brand new Cabins.

This house is a 0 bedroom(s), 2 bathrooms, located in Frankfort, KY.

This house is a 0 bedroom(s), 2 bathrooms, located in Frankfort, KY.
2.0 star property
Frankfort
9.6 out of 10, Exceptional, (14)
"Very nice kept and clean will be booking again "
United States
Donald
The price is ¥23,372
¥41,337 total
includes taxes & fees
Jan 13 - Jan 14, 2026
This house is a 0 bedroom(s), 2 bathrooms, located in Frankfort, KY.

Bourbon Trail Lakehouse - Pet Friendly!

Bourbon Trail Lakehouse - Pet Friendly!
Frankfort
9.8 out of 10, Exceptional, (50)
"Great place to stay!"
United States
Jeff S.
The price is ¥15,215
¥41,642 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Bourbon Trail Lakehouse - Pet Friendly!

Two Bourbon Barrel Cabins

Two Bourbon Barrel Cabins
Frankfort
10.0 out of 10, Exceptional, (17)
"Fun place to stay. Cabins were super cute!"
United States
Rebecca B.
The price is ¥49,859
¥77,049 total
includes taxes & fees
Dec 16 - Dec 17
Two Bourbon Barrel Cabins

Bourbon Trail Cabin on the Farm

Bourbon Trail Cabin on the Farm
Lawrenceburg
10.0 out of 10, Exceptional, (46)
"Fantastic location and great hosts!"
United States
James S.
The price is ¥14,724
¥27,743 total
includes taxes & fees
Dec 17 - Dec 18
Bourbon Trail Cabin on the Farm

The Carriage - Quaint Haven 6 mins. to Buffalo Trace

The Carriage - Quaint Haven 6 mins. to Buffalo Trace
Frankfort
10.0 out of 10, Exceptional, (22)
"The Vrbo was cozy & in a quiet location. "
United States
Teresa V.
The price is ¥12,739
¥29,655 total
includes taxes & fees
Dec 15 - Dec 16
The Carriage - Quaint Haven 6 mins. to Buffalo Trace

Spacious Ranch in Frankfort.

Spacious Ranch in Frankfort.
Frankfort
9.8 out of 10, Exceptional, (46)
"Clean and plenty of room! Beds were comfortable and kitchen was spacious. Would definitely stay again!"
United States
Michelle R.
The price is ¥23,216
¥59,556 total
includes taxes & fees
Dec 15 - Dec 16
Spacious Ranch in Frankfort.

Ideal One-Bedroom Getaway on the Bourbon Trail

Ideal One-Bedroom Getaway on the Bourbon Trail
LAWRENCBURG
10.0 out of 10, Exceptional, (13)
"This little house was perfect. Very clean and well-kept. Modernly decorated. Walking distance to the little downtown area, the park and the town square. We loved our short stay! "
United States
Kristi
The price is ¥16,360
¥30,059 total
includes taxes & fees
Dec 22 - Dec 23
Ideal One-Bedroom Getaway on the Bourbon Trail

The Bourbon Garage- walking distance to Buffalo Trace!

The Bourbon Garage- walking distance to Buffalo Trace!
Frankfort
10.0 out of 10, Exceptional, (8)
"Super convenient to buffalo trace. Comfortable space. Would recommend "
United States
Brandy
The price is ¥15,737
¥38,133 total
includes taxes & fees
Dec 15 - Dec 16
The Bourbon Garage- walking distance to Buffalo Trace!

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, (19)
"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 ¥13,244
¥31,140 total
includes taxes & fees
Dec 15 - Dec 16
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

Capital City Cottage

Capital City Cottage
Frankfort
8.6 out of 10, Excellent, (43)
"Cute little cottage. Great for 2. Very clean and centrally located to many things in the area. "
United States
Matt T.
The price is ¥15,581
¥37,581 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Capital City Cottage
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

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:

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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?

"Centrally Located to Many Distilleries" House on the Kentucky Bourbon Trail: This vacation home rental outside of Waddy is located on a river and has a selection of games, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals are there in Waddy?

With 4 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 Berry Hill Mansion and Talon Winery.

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.