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Compare 164 Vacation Homes in Waddy with updated reviews, rates, and availability.

KY Bourbon Trail FUN! Double Shot on Main 2 Bed/2 Bath
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KY Bourbon Trail FUN! Double Shot on Main 2 Bed/2 Bath

10.0 out of 10, Exceptional, (79)
"This house is clean and well located. It is not fancy, but it is lots of fun! We came with another couple for the bourbon trail and to see the horses. At the end of each day, instead of watching TV, we took advantage of the wonderful selection of games. We played darts, cards, and chess. It made a great trip even better. "
The price is SAR 507
SAR 640 total
includes taxes & fees
4 Dec - 5 Dec
KY Bourbon Trail FUN! Double Shot on Main 2 Bed/2 Bath
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.
Living area

This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.

9.4 out of 10, Exceptional, (36)
"Everything was perfect! Only thing was parking was difficult with our F150 truck but we knew that going in from other reviews! Would stay again for sure!! "
The price is SAR 225
SAR 582 total
includes taxes & fees
24 Nov - 25 Nov
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.
Bourbon Trail / Ark Encounter / Horse Racing: Cabin, Fishing, Hunting, & Firepit
Exterior

Bourbon Trail / Ark Encounter / Horse Racing: Cabin, Fishing, Hunting, & Firepit

10.0 out of 10, Exceptional, (47)
"This our third time staying here. It never gets old, treat yourself to a top notch Vrbo such as this one you will not regret it."
Bourbon Trail / Ark Encounter / Horse Racing: Cabin, Fishing, Hunting, & Firepit
The Bourbon Charm Homestay. Bourbon Trail, PGA, Derby
Living area

The Bourbon Charm Homestay. Bourbon Trail, PGA, Derby

10.0 out of 10, Exceptional, (13)
"The house was very clean and quiet, with a huge TV in the common room. A short drive to Bardstown and other stops on the bourbon trail."
The Bourbon Charm Homestay. Bourbon Trail, PGA, Derby
Bourbon and Horse Racing
Exterior

Bourbon and Horse Racing

9.8 out of 10, Exceptional, (15)
"Really a wonderful time with so many distillers less the 20 min away in every direction. Loved the place and it was a good fit for a small friend group "
The price is SAR 657
SAR 1,320 total
includes taxes & fees
24 Nov - 25 Nov
Bourbon and Horse Racing
Two Miles to Buffalo Trace > Speakeasy > Hot Tub > Gas Fire Pit
Welcome to the Bluegrass Bourbon House!

Two Miles to Buffalo Trace > Speakeasy > Hot Tub > Gas Fire Pit

10.0 out of 10, Exceptional, (4)
"The stay was perfect. We enjoyed the theme of the house and cleanliness. Location in Frankfort for walkability to restaurants was ideal. Had a great comfortable stay and communication was great. Would stay again. Thanks."
Two Miles to Buffalo Trace > Speakeasy > Hot Tub > Gas Fire Pit
KY BOURBON TRAIL LAKEFRONT HOUSE WITH DOCK SLEEPS 8! Year round Hot tub!

KY BOURBON TRAIL LAKEFRONT HOUSE WITH DOCK SLEEPS 8! Year round Hot tub!

9.8 out of 10, Exceptional, (106)
"Was a very nice cottage, would definitely recommend to others"
KY BOURBON TRAIL LAKEFRONT HOUSE WITH DOCK SLEEPS 8! Year round Hot tub!
Spacious Ranch in Frankfort.
Living area

Spacious Ranch in Frankfort.

9.8 out of 10, Exceptional, (30)
"Wonderful property with a few minor issues like slow shower drain and no dishwasher soap. Lots of room to spread out. Enjoyed corn hole in the backyard."
The price is SAR 559
SAR 1,443 total
includes taxes & fees
25 Nov - 26 Nov
Spacious Ranch in Frankfort.
Bourbon Trail Lakehouse - Pet Friendly!
Living room

Bourbon Trail Lakehouse - Pet Friendly!

9.8 out of 10, Exceptional, (27)
"Great communication with the host and a very clean place. We didn’t realize that it was an attached house so there wasn’t much privacy on the deck, and the furniture out there was pretty beat up. However it was very quiet and a residential neighborhood near the highway. "
The price is SAR 419
SAR 1,066 total
includes taxes & fees
24 Nov - 25 Nov
Bourbon Trail Lakehouse - Pet Friendly!
3 Bedroom 2 Bath home located on farm land/private but only 2 minutes from town.
Exterior

3 Bedroom 2 Bath home located on farm land/private but only 2 minutes from town.

10.0 out of 10, Exceptional, (12)
"Great place- enjoyed the location and the friendly 4 feet neighbors! Great communication. Will stay here again."
The price is SAR 597
SAR 1,177 total
includes taxes & fees
24 Nov - 25 Nov
3 Bedroom 2 Bath home located on farm land/private but only 2 minutes from town.
Bourbon Trail Downtown Frankfort w/Game Room
Game room

Bourbon Trail Downtown Frankfort w/Game Room

9.8 out of 10, Exceptional, (16)
"Nice roomy house that’s very well laid out for guests. The host has really gone out of their way to make the stay easy and pleasant. We were amazed by all the extra “essentials” provided. If you forgot to pack something, other than clothes, it’s probably available in the home. We’ll definitely stay there on our next visit to Bourbon country!"
The price is SAR 747
SAR 1,329 total
includes taxes & fees
24 Nov - 25 Nov
Bourbon Trail Downtown Frankfort w/Game Room
Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill
Shelbyville Vacation Rental | 3BR | 2BA | 1,700 Sq Ft | Steps Required to Access

Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill

9.6 out of 10, Exceptional, (9)
"Cute house, clean, fun spot"
Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill
New luxury apartment in downtown Frankfort next to Distilleries. Near everything
Private kitchen

New luxury apartment in downtown Frankfort next to Distilleries. Near everything

10.0 out of 10, Exceptional, (21)
"My wife and I just returned from wonderful stay in KY including this spot in downtown Frankfort. This was our first stay in the area, but we will be back. The owner was available to answer any questions and even reached out to us to see if we needed anything upon arrival. Great location; clean and comfortable place in the heart of Frankfort. Loved the decor as well as the convenient location for restaurants and bars as well as experiencing bourbon distilleries. "
New luxury apartment in downtown Frankfort next to Distilleries. Near everything
Valhalla View Home-Minutes to Golf Course-Perfect for Golfers, Horses, Trailers
Exterior

Valhalla View Home-Minutes to Golf Course-Perfect for Golfers, Horses, Trailers

10.0 out of 10, Exceptional, (2)
"Your property was exactly as advertised and exceeded all expectations. "
Valhalla View Home-Minutes to Golf Course-Perfect for Golfers, Horses, Trailers
Secluded Retreat in Scenic Frankfort w/ Hot Tub: Whiskey Woods - Book Now!
Living area

Secluded Retreat in Scenic Frankfort w/ Hot Tub: Whiskey Woods - Book Now!

9.8 out of 10, Exceptional, (9)
"Great weekend touring bourbon trail! Excellent location, so clean and new, and very responsive host when our WiFi went out. He quickly came and fixed it!"
The price is SAR 657
SAR 1,207 total
includes taxes & fees
25 Nov - 26 Nov
Secluded Retreat in Scenic Frankfort w/ Hot Tub: Whiskey Woods - Book Now!
Carriage on Petticoat
Exterior

Carriage on Petticoat

2.0 star property
10.0 out of 10, Exceptional, (4)
"6 of us (3 couples) stayed at he house this weekend. The bedrooms were large and comfortable. The kitchen and seating made it easy for all of us to cook and eat together. The second floor entertainment / hang out area was super comfortable and cozy. We're coming back again!"
The price is SAR 657
SAR 1,367 total
includes taxes & fees
10 Dec - 11 Dec
Carriage on Petticoat
Blissful Home, Frankfort KY
Living area

Blissful Home, Frankfort KY

9.4 out of 10, Exceptional, (13)
"We checked in late and left early but fit our needs well! "
Blissful Home, Frankfort KY
New Luxury Brbn Trail w HotTub + GameRoom + Sauna
Enjoy the outdoors in this stunning fire pit area. With seating for 12, there's plenty of space to relax and enjoy the fire. At night the lights illuminate the countryside, providing a picturesque backdrop for unforgettable evenings under the stars.

New Luxury Brbn Trail w HotTub + GameRoom + Sauna

10.0 out of 10, Exceptional, (49)
"This was a short vacation with friends that enjoy bourbon and spending g time together. The home was outstanding!"
New Luxury Brbn Trail w HotTub + GameRoom + Sauna
Angels Envy 29 - A relaxing place by the lake!

Angels Envy 29 - A relaxing place by the lake!

9.6 out of 10, Exceptional, (14)
"Great place good accommodation "
The price is SAR 507
SAR 1,128 total
includes taxes & fees
24 Nov - 25 Nov
Angels Envy 29 - A relaxing place by the lake!
Lakefront Home Close to Bourbon Trail--Dog friendly and now with WiFi!
Property grounds

Lakefront Home Close to Bourbon Trail--Dog friendly and now with WiFi!

9.8 out of 10, Exceptional, (65)
"Nice, quiet place to decompress during a long weekend. It was in close proximity to the bourbon trail, so that was an added bonus. The pups had a blast too."
Lakefront Home Close to Bourbon Trail--Dog friendly and now with WiFi!
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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Other property types in Waddy

Luxury lodge in the heart of the Bluegrass
Living area

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 SAR 4,318
SAR 7,037 total
includes taxes & fees
25 Nov - 26 Nov
Luxury lodge in the heart of the Bluegrass
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.
Living area

This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.

9.4 out of 10, Exceptional, (36)
"Everything was perfect! Only thing was parking was difficult with our F150 truck but we knew that going in from other reviews! Would stay again for sure!! "
The price is SAR 225
SAR 582 total
includes taxes & fees
24 Nov - 25 Nov
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.
Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail
Seating for 6 in this cozy living room with fire place & 42-inch SMART LCD TV

Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail

10.0 out of 10, Exceptional, (197)
"I am a 65 YO woman and I stayed at this cottage by myself the week of 10/22/24. I am pleased to give a 5-star rating because: this cottage was easy to find and located in a pleasant, quiet area. I felt safe in this cottage; it was very clean; bed slept wonderful; water pressure and temp were great; cottage looks exactly like pictures; everything worked as expected, and my communications with the property manager were easy. This area is wonderful if you want peace and quiet, close to the lake...
Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail
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.