Waddy Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Waddy vacation rentals

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 location, close to Frankfort, Louisville and Lexington. Theater room was amazing! "
United States
Nicole D.
The price is CA $1,817
CA $2,848 total
includes taxes & fees
Feb 27 - Feb 28
Luxury lodge in the heart of the Bluegrass

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, (3 reviews)
"Wonderful location and fantastic space for our family! "
United States
Erica R.
The price is CA $369
CA $1,052 total
includes taxes & fees
Feb 23 - Feb 24
Private 7 Acre Estate 6-Bdrm Home+Putting Green+Theatre+Hot Tub+Game Rm+Fire Pit

Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views

Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views
Waddy
8.0 out of 10, Very good, (10 reviews)
"Clean, quiet and a great location. "
United States
Marla B.
The price is CA $142
CA $388 total
includes taxes & fees
Feb 21 - Feb 22
Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views

The Ridge: 6BR • 100" TV • Hot Tub • Speakeasy

The Ridge: 6BR • 100" TV • Hot Tub • Speakeasy
Waddy
10.0 out of 10, Exceptional, (1 review)
"Thirteen of us escaped to Cat Ridge Resort for a quick stay—and left planning our return.The scenic drive and peaceful setting set the tone. Evenings by the firepit, hot tub soaks under the stars, and time in the sauna made it easy to unwind. The cows next door were a charming bonus.Inside, the design is stunning—thoughtful, handcrafted details and beautiful spaces made for gathering.Communication with the host was excellent, and check-in was a breeze.Short, sweet, and truly special. We can’t...
United States
Barb J.
The price is CA $173
CA $1,191 total
includes taxes & fees
Feb 23 - Feb 24
The Ridge: 6BR • 100" TV • Hot Tub • Speakeasy

Bourbon Trail: Caboose on the Farm

Bourbon Trail: Caboose on the Farm
Lawrenceburg
10.0 out of 10, Exceptional, (38 reviews)
"Loved every aspect of this unique stay! From the very cool caboose to friendly farm animals, we hope to be back again!"
United States
Cindi M.
The price is CA $193
CA $321 total
includes taxes & fees
Feb 23 - Feb 24
Bourbon Trail: Caboose on the Farm

2 Bed/2 Bath/Game Room

2 Bed/2 Bath/Game Room
Lawrenceburg
10.0 out of 10, Exceptional, (123 reviews)
"Great central location for our stay! Than you so much. Would absolutely recommend this to everyone!"
United States
Patrick
The price is CA $177
CA $290 total
includes taxes & fees
Feb 19 - Feb 20
2 Bed/2 Bath/Game Room

Five Minutes from Keeneland!

Five Minutes from Keeneland!
Versailles
10.0 out of 10, Exceptional, (23 reviews)
"In Bluegrass Country yet close to Keeneland and all the other important places and activities around Lexington and surrounds. "
United States
Thomas M.
The price is CA $247
CA $439 total
includes taxes & fees
Feb 21 - Feb 22
Five Minutes from Keeneland!

Restful Bourbon Trail Lodge with Pool and Hot Tub

Restful Bourbon Trail Lodge with Pool and Hot Tub
Lawrenceburg
9.6 out of 10, Exceptional, (27 reviews)
"Everything was very nice and clean"
United States
Ryan W.
The price is CA $253
CA $489 total
includes taxes & fees
Feb 23 - Feb 24
Restful Bourbon Trail Lodge with Pool and Hot Tub

Bourbon Barrel Cottages #3 on Ky. Bourbon Trail

Bourbon Barrel Cottages #3 on Ky. Bourbon Trail
Lawrenceburg
10.0 out of 10, Exceptional, (18 reviews)
"We really enjoyed our stay at the bourbon barrel cottage. Would highly recommend and will book again when we are in the area."
United States
Stephanie B.
The price is CA $286
CA $1,814 total
includes taxes & fees
Mar 15 - Mar 16
Bourbon Barrel Cottages #3 on Ky. Bourbon Trail

KY Bourbon Trail Home, King Bed, FirePit, Near Louisville

KY Bourbon Trail Home, King Bed, FirePit, Near Louisville
Shelbyville
9.8 out of 10, Exceptional, (8 reviews)
"The perfect location for a quick stop on the bourbon trail. Ten minutes from Bulleit, down the road from Jeptha Creed, and a short hop over to Buffalo Trace and downtown Louisville!"
United States
Shay D.
The price is CA $188
CA $446 total
includes taxes & fees
Mar 4 - Mar 5
KY Bourbon Trail Home, King Bed, FirePit, Near Louisville

Two Bourbon Barrel Cabins

Two Bourbon Barrel Cabins
Frankfort
10.0 out of 10, Exceptional, (17 reviews)
"Fun place to stay. Cabins were super cute!"
United States
Rebecca B.
The price is CA $382
CA $625 total
includes taxes & fees
Feb 23 - Feb 24
Two Bourbon Barrel Cabins

Luxury 6BR Bourbon Farmhouse w/ Spa & SpeakEasy

Luxury 6BR Bourbon Farmhouse w/ Spa & SpeakEasy
Lawrenceburg
10.0 out of 10, Exceptional, (73 reviews)
"This was an incredible property to stay at, probably the best I've stayed at. Very smooth and easy check-in and check-out and responsive hosts."
United States
Kyle R.
The price is CA $505
CA $1,280 total
includes taxes & fees
Feb 22 - Feb 23
Luxury 6BR Bourbon Farmhouse w/ Spa & SpeakEasy

# 1 on Ky. Bourbon Trail HOT TUB all distilleries

# 1 on Ky. Bourbon Trail HOT TUB all distilleries
Lawrenceburg
10.0 out of 10, Exceptional, (26 reviews)
"Great, secluded location far enough away for peace and quiet yet close enough to lots of fun activities."
United States
Kevin B.
The price is CA $286
CA $491 total
includes taxes & fees
Feb 19 - Feb 20
# 1 on Ky. Bourbon Trail HOT TUB all distilleries

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, (97 reviews)
"We enjoyed our stay while we were down for Breyer Fest. It was close to places we wanted to go and quiet. We would definitely stay here again."
United States
Jacob Y.
The price is CA $95
CA $225 total
includes taxes & fees
Feb 23 - Feb 24
Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.

Greenwood Farm log cabin close to the Bourbon Trail and Keeneland

Greenwood Farm log cabin close to the Bourbon Trail and Keeneland
Versailles
10.0 out of 10, Exceptional, (33 reviews)
"Perfect for our needs.Came up for keenland and the Kentucky Tennessee game. Was a perfect spot for us and everything was exactly as described. Had a blast and the property is super pretty. Will be coming back again! "
United States
Austin S.
The price is CA $334
CA $633 total
includes taxes & fees
Feb 19 - Feb 20
Greenwood Farm log cabin close to the Bourbon Trail and Keeneland

Bourbon Barrel Cottages #5 on Ky. Bourbon Trail

Bourbon Barrel Cottages #5 on Ky. Bourbon Trail
Lawrenceburg
10.0 out of 10, Exceptional, (14 reviews)
"Very clean place to stay. "
United States
Alisha F.
The price is CA $286
CA $491 total
includes taxes & fees
Feb 23 - Feb 24
Bourbon Barrel Cottages #5 on Ky. Bourbon Trail

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, (82 reviews)
"We had a great stay at this property. The space was clean, well-stocked with supplies, and the hosts were responsive. I would recommend this location to anyone visiting the area. "
United States
Lisa E.
The price is CA $95
CA $225 total
includes taxes & fees
Mar 5 - Mar 6
Capital City Condo #1 close to Interstate, Water Park, Restaurants and Shopping

Seabiscuit 5- Relax And Kick Back (Decorated for the 2025 Christmas Season)

Seabiscuit 5- Relax And Kick Back (Decorated for the 2025 Christmas Season)
Taylorsville
9.6 out of 10, Exceptional, (54 reviews)
"We had a girls weekend and everything was perfect. Would definitely stay here again."
United States
Susan N.
The price is CA $185
CA $369 total
includes taxes & fees
Feb 19 - Feb 20
Seabiscuit 5- Relax And Kick Back (Decorated for the 2025 Christmas Season)

Capital City Condo #8

Capital City Condo #8
Frankfort
8.6 out of 10, Excellent, (36 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 CA $95
CA $225 total
includes taxes & fees
Feb 23 - Feb 24
Capital City Condo #8

Bourbon Trail Lakehouse - Pet Friendly!

Bourbon Trail Lakehouse - Pet Friendly!
Frankfort
9.8 out of 10, Exceptional, (52 reviews)
"Great place to stay!"
United States
Jeff S.
The price is CA $115
CA $344 total
includes taxes & fees
Feb 19 - Feb 20
Bourbon Trail Lakehouse - Pet Friendly!
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.

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Waddy Hotel Reviews

Find out more about Waddy

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Waddy. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Heated Pool, Hot Tub, Mini Golf, Theater-Sleeps 28: This vacation home rental outside of Waddy is located on the waterfront and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 9 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 5 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.