Waddy Holiday Rentals

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Holiday Rentals in Waddy

The Havilah House! Country living with amazing views!
10.0 out of 10, Exceptional, (30)
"I met my 8 girlfriends from college in central Kentucky. The Havilah House was the perfect location for keeneland and bourbon tours and halfway between the bluegrass and Louisville airports. The house is comfortable and well stocked. The host was very responsive and answered our questions quickly. I would highly recommend it."
The Havilah House! Country living with amazing views!
Luxury lodge in the heart of the Bluegrass
10.0 out of 10, Exceptional, (4)
"Let’s start with the negative…I am only allowed to rate the property on 5 stars, instead of a WELL DESERVING 10!!! This place is amazing! The home (not house, there is more than enough character to go around which puts it on another level as far as I’m concerned) is located conveniently off the highway and is situated on meticulously maintained grounds. Plenty of space to host a larger crowd or spread out and seek privacy. We’ve stayed in numerous different areas around the country and this...
The price is NZ$2,405
per night
12 Jun - 13 Jun
Luxury lodge in the heart of the Bluegrass
Capital City Cottage
9.8 out of 10, Exceptional, (9)
"This house is in a cute historic neighborhood close to the capital. Perfect for morning and evening walks. Less than 10 minutes to Buffalo Trace distillery. House was clean and comfortable. Would definitely stay here again!"
The price is NZ$387
per night
2 Jul - 3 Jul
Capital City Cottage
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Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.
9.0 out of 10, Wonderful, (69)
"Clean & Cute! "
The price is NZ$247
per night
10 Jun - 11 Jun
Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.
Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail
10.0 out of 10, Exceptional, (178)
"A+++"
Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.
9.0 out of 10, Wonderful, (22)
"The code was showing on the wall next to the door which made us feel less than safe. I tried to contact the owner and he never responded. The sofa smelt like someone peed in it. The bedroom close to the kitchen had a mold smell. But the most worrying issue was the shower that was in the bathtub was on a platform with no rail to hold on to in order to get out safely. Otherwise we enjoyed the house."
The price is NZ$257
per night
10 Jun - 11 Jun
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.
"Centrally Located to Many Distilleries" House on the Kentucky Bourbon Trail
9.8 out of 10, Exceptional, (88)
"Family was in town for a local graduation so we rented this property rather than get a hotel room. The creek was gorgeous, outdoor space was perfect, and the home is gorgeous and well maintained!"
"Centrally Located to Many Distilleries" House on the Kentucky Bourbon Trail
2024 KY Derby 30 min Away ~ Art Gallery ~ Hot Tub
10.0 out of 10, Exceptional, (12)
"We so enjoyed this house. It had everything we needed. The house is beautiful with three bedrooms and bathrooms. The kitchen was so very nice with lots of extras. We thoroughly enjoyed the porch. So nice to relax and enjoy the weather. The location was excellent and it was within walking distance to restaurants and boutiques. The 6 of us loved it!!"
2024 KY Derby 30 min Away ~ Art Gallery ~ Hot Tub
Family-Friendly Versailles House: 12 Mi to UK!
10.0 out of 10, Exceptional, (2)
"Great location to visit horse farms, racetrack, and distilleries."
Family-Friendly Versailles House: 12 Mi to UK!
Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin
9.8 out of 10, Exceptional, (189)
"Great property and had a wonderful time. Only problem we had was the large gas grill needed cleaning. When we used it, it caught fire because of all the grease buildup below grate. We had to shut it down."
The price is NZ$1,085
per night
5 Jun - 6 Jun
Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin
KY Bourbon Trail FUN! Double Shot on Main 2 Bed/2 Bath
10.0 out of 10, Exceptional, (59)
"The property was perfect for a quick bourbon trail getaway with friends. It has everything you need a for a comfortable stay."
KY Bourbon Trail FUN! Double Shot on Main 2 Bed/2 Bath
Spacious Kentucky Home in the Heart of Derby and Bourbon Country
10.0 out of 10, Exceptional, (1)
"Our family had a great stay in Mount Washington for Thanksgiving. We had three generations in the house staying together, and it was perfect for what we all needed. Every bedroom except one has its own connected bathroom, which made showers and getting ready so easy. Amazingly, we never ran out of hot water! Big plus! The house has been completely renovated and everything is new and beautiful. The kitchen was perfectly stocked with everything we needed for cooking. The TVs were connected to...
Spacious Kentucky Home in the Heart of Derby and Bourbon Country
Lakefront Home Close to Bourbon Trail--Dog friendly and now with WiFi!
9.8 out of 10, Exceptional, (52)
"Great place to stay! Loved the location. Felt like backwoods yet very close to several of the area’s bourbon trail stops and an easy drive to Frankfort and Lexington."
Lakefront Home Close to Bourbon Trail--Dog friendly and now with WiFi!
Bourbon Trail Cabin on the Farm
10.0 out of 10, Exceptional, (15)
"This beautiful cabin is in the heart of rolling hills! It was spotlessly cleaned and smelled so fresh! Beautiful outside areas including fireplace and outdoor furniture and games! Short drive to distilleries and wineries! Kim and Ryan were so gracious! Will make this a yearly retreat! A big plus- cats, goats, cows and Otis the donkey!!!"
The price is NZ$267
per night
11 Jun - 12 Jun
Bourbon Trail Cabin on the Farm
1 Bedroom KY Bourbon Trail Loft in Horse Country
10.0 out of 10, Exceptional, (23)
"This is where you want to stay in Frankfort. Nice place. Perfect location. Excellent host. We enjoyed our time there and had zero complaints."
The price is NZ$333
per night
5 Jun - 6 Jun
1 Bedroom KY Bourbon Trail Loft in Horse Country
GET AWAY FROM IT ALL - Cottage 28 Taylorsville Lake
9.4 out of 10, Exceptional, (22)
"Yearly my wife and I get away just to enjoy our time together. This is the second year in a row we stayed at this location and we are planning on next year already. The cabin is so relaxing and the host is outstanding in communicating with us before our arrival. This is the place to be. Thank you for an enjoyable time."
GET AWAY FROM IT ALL - Cottage 28 Taylorsville Lake
Secluded "New" 2 Bedroom Sanctuary on 20 Acres in the Heart of the Bourbon Trail
10.0 out of 10, Exceptional, (33)
"The cabin is everything described in the listing. Very clean, inviting and well decorated. It was so peaceful sitting on the porch watching the wildlife and hearing the birds chirp while drinking your morning coffee. The owners were very nice and easy to work with. We would definitely recommend this cabin to friends and family. We were there exploring the Bourbon as a weekend getaway."
Secluded "New" 2 Bedroom Sanctuary on 20 Acres in the Heart of the Bourbon Trail
The Green Cabin-on-The Bourbon Trail
9.8 out of 10, Exceptional, (179)
"We enjoyed our stay. The place was great"
The Green Cabin-on-The Bourbon Trail
Historically Registered 1847 log Cabin
10.0 out of 10, Exceptional, (129)
"Had a great stay at this home for the PGA championship. Home was clean, comfortable and in a great location. Property was peaceful and beautiful and would be great for families with kids. Hosts Tim and Lynn were amazing! Highly recommend!"
Historically Registered 1847 log Cabin
25% off June! Classic Kentucky Farm to host your Bluegrass Bourbon Adventure
10.0 out of 10, Exceptional, (26)
"We wish we had planned to stay longer! The house and the property is ideal! We very much enjoyed the outdoor seating and fire pit. The bedrooms were all well appointed and very comfortable. We would definitely plan to stay here again if we travel back to the area."
25% off June! Classic Kentucky Farm to host your Bluegrass Bourbon Adventure
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See all available properties in Waddy
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.

Other types of properties in Waddy you may be interested in

The Havilah House! Country living with amazing views!
10.0 out of 10, Exceptional, (30)
"I met my 8 girlfriends from college in central Kentucky. The Havilah House was the perfect location for keeneland and bourbon tours and halfway between the bluegrass and Louisville airports. The house is comfortable and well stocked. The host was very responsive and answered our questions quickly. I would highly recommend it."
The Havilah House! Country living with amazing views!
Luxury lodge in the heart of the Bluegrass
10.0 out of 10, Exceptional, (4)
"Let’s start with the negative…I am only allowed to rate the property on 5 stars, instead of a WELL DESERVING 10!!! This place is amazing! The home (not house, there is more than enough character to go around which puts it on another level as far as I’m concerned) is located conveniently off the highway and is situated on meticulously maintained grounds. Plenty of space to host a larger crowd or spread out and seek privacy. We’ve stayed in numerous different areas around the country and this...
The price is NZ$2,405
per night
12 Jun - 13 Jun
Luxury lodge in the heart of the Bluegrass
Capital Plaza Hotel
3.0 star property
8.4 out of 10, Very good, (1009)
"No parking on the property. Put dirty linens outside my door to be replaced. Had to go to front desk in the evening to get clean one and other things I needed. Breakfast was great and staff there was friendly!!"
The price is NZ$257
per night
5 Jun - 6 Jun
Capital Plaza Hotel
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Waddy holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Waddy. 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 Waddy. 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 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 holiday 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 Waddy short-term rentals, that won’t be hard to do.

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?

The Havilah House! Country living with amazing views! : This highly rated holiday home rental in Waddy is located in a rural location, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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 Salato Wildlife Education Center and Kentucky State Capitol.

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.

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