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Waddy Vacation Rentals

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Bathrooms

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5 km
49 rentals in Waddy.
Luxury 4 bedroom Log Cabin on 32 acres only 10 minutes from Frankfort, KY, vacation rental in Waddy
Luxury 4 bedroom Log Cabin on 32 acres only 10 minutes from Frankfort, KY, vacation rental in Waddy
Luxury 4 bedroom Log Cabin on 32 acres only 10 minutes from Frankfort, KY, vacation rental in Waddy

Luxury 4 bedroom Log Cabin on 32 acres only 10 minutes from Frankfort, KY

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Luxury lodge in the heart of the Bluegrass, vacation rental in Waddy
Luxury lodge in the heart of the Bluegrass, vacation rental in Waddy
Luxury lodge in the heart of the Bluegrass, vacation rental in Waddy

Luxury lodge in the heart of the Bluegrass

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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✨Luxe Farmhouse✨Bourbon Trail✨ 4 king Beds ✨Hot Tub Games Trails sleeps 16, vacation rental in Waddy
✨Luxe Farmhouse✨Bourbon Trail✨ 4 king Beds ✨Hot Tub Games Trails sleeps 16, vacation rental in Waddy
✨Luxe Farmhouse✨Bourbon Trail✨ 4 king Beds ✨Hot Tub Games Trails sleeps 16, vacation rental in Waddy

✨Luxe Farmhouse✨Bourbon Trail✨ 4 king Beds ✨Hot Tub Games Trails sleeps 16

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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The following properties within 32 kms of Waddy match all your filters:
New Luxury Brbn Trail w HotTub + GameRoom + Sauna, vacation rental in Waddy
New Luxury Brbn Trail w HotTub + GameRoom + Sauna, vacation rental in Waddy
New Luxury Brbn Trail w HotTub + GameRoom + Sauna, vacation rental in Waddy

New Luxury Brbn Trail w HotTub + GameRoom + Sauna

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin, Sleeps 29!, vacation rental in Waddy
Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin, Sleeps 29!, vacation rental in Waddy
Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin, Sleeps 29!, vacation rental in Waddy

Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin, Sleeps 29!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 29
Match: Sleeps
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Peaceful Farmhouse Retreat Frankfort, Kentucky, vacation rental in Waddy
Peaceful Farmhouse Retreat Frankfort, Kentucky, vacation rental in Waddy
Peaceful Farmhouse Retreat Frankfort, Kentucky, vacation rental in Waddy

Peaceful Farmhouse Retreat Frankfort, Kentucky

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Historic home freshly renovated on the Bourbon Trail, vacation rental in Waddy
Historic home freshly renovated on the Bourbon Trail, vacation rental in Waddy
Historic home freshly renovated on the Bourbon Trail, vacation rental in Waddy

Historic home freshly renovated on the Bourbon Trail

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Spacious Ranch in Frankfort., vacation rental in Waddy
Spacious Ranch in Frankfort., vacation rental in Waddy
Spacious Ranch in Frankfort., vacation rental in Waddy

Spacious Ranch in Frankfort.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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KY Bourbon Trail Home, King Bed, FirePit, Near Louisville, vacation rental in Waddy
KY Bourbon Trail Home, King Bed, FirePit, Near Louisville, vacation rental in Waddy
KY Bourbon Trail Home, King Bed, FirePit, Near Louisville, vacation rental in Waddy

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

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Bourbon Country CabinLoft style cabin, great location to visit KY, vacation rental in Waddy
Bourbon Country CabinLoft style cabin, great location to visit KY, vacation rental in Waddy
Bourbon Country CabinLoft style cabin, great location to visit KY, vacation rental in Waddy

Bourbon Country CabinLoft style cabin, great location to visit KY

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Your Kentucky Home Away From Home, vacation rental in Waddy
Your Kentucky Home Away From Home, vacation rental in Waddy
Your Kentucky Home Away From Home, vacation rental in Waddy

Your Kentucky Home Away From Home

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful restored Victorian farmhouse, vacation rental in Waddy
Beautiful restored Victorian farmhouse, vacation rental in Waddy
Beautiful restored Victorian farmhouse, vacation rental in Waddy

Beautiful restored Victorian farmhouse

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Unique Downtown Studio with an Industrial Vibe, vacation rental in Waddy
Unique Downtown Studio with an Industrial Vibe, vacation rental in Waddy
Unique Downtown Studio with an Industrial Vibe, vacation rental in Waddy

Unique Downtown Studio with an Industrial Vibe

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi, vacation rental in Waddy
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi, vacation rental in Waddy
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi, vacation rental in Waddy

Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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H-DERBY, Keeneland, Bourbon or Family Gathering!, vacation rental in Waddy
H-DERBY, Keeneland, Bourbon or Family Gathering!, vacation rental in Waddy
H-DERBY, Keeneland, Bourbon or Family Gathering!, vacation rental in Waddy

H-DERBY, Keeneland, Bourbon or Family Gathering!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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2024 KY Derby 30 min Away ~ Art Gallery ~ Hot Tub, vacation rental in Waddy
2024 KY Derby 30 min Away ~ Art Gallery ~ Hot Tub, vacation rental in Waddy
2024 KY Derby 30 min Away ~ Art Gallery ~ Hot Tub, vacation rental in Waddy

2024 KY Derby 30 min Away ~ Art Gallery ~ Hot Tub

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Luxury farmhouse on Bourbon Trail with hot tub - Bulleit 4 mi - Frankfort 15 mi, vacation rental in Waddy
Luxury farmhouse on Bourbon Trail with hot tub - Bulleit 4 mi - Frankfort 15 mi, vacation rental in Waddy
Luxury farmhouse on Bourbon Trail with hot tub - Bulleit 4 mi - Frankfort 15 mi, vacation rental in Waddy

Luxury farmhouse on Bourbon Trail with hot tub - Bulleit 4 mi - Frankfort 15 mi

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Upscale Kentucky Bourbon Trail & Close to Louisville, vacation rental in Waddy
Upscale Kentucky Bourbon Trail & Close to Louisville, vacation rental in Waddy
Upscale Kentucky Bourbon Trail & Close to Louisville, vacation rental in Waddy

Upscale Kentucky Bourbon Trail & Close to Louisville

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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LeCoop Ultra Luxury 2 bed Loft on Bourbon Trail.Close to BuffaloTrace and others, vacation rental in Waddy
LeCoop Ultra Luxury 2 bed Loft on Bourbon Trail.Close to BuffaloTrace and others, vacation rental in Waddy
LeCoop Ultra Luxury 2 bed Loft on Bourbon Trail.Close to BuffaloTrace and others, vacation rental in Waddy

LeCoop Ultra Luxury 2 bed Loft on Bourbon Trail.Close to BuffaloTrace and others

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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oasis 522!, vacation rental in Waddy
oasis 522!, vacation rental in Waddy
oasis 522!, vacation rental in Waddy

oasis 522!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Bourbon Country Cottage Newly renovated  in the country with amazing views, vacation rental in Waddy
Bourbon Country Cottage Newly renovated  in the country with amazing views, vacation rental in Waddy
Bourbon Country Cottage Newly renovated  in the country with amazing views, vacation rental in Waddy

Bourbon Country Cottage Newly renovated in the country with amazing views

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Horses, Bourbon and More .... Shelbyville Condo, vacation rental in Waddy
Horses, Bourbon and More .... Shelbyville Condo, vacation rental in Waddy
Horses, Bourbon and More .... Shelbyville Condo, vacation rental in Waddy

Horses, Bourbon and More .... Shelbyville Condo

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Bourbon Trail , Cheerful 2 bedroom home, vacation rental in Waddy
Bourbon Trail , Cheerful 2 bedroom home, vacation rental in Waddy
Bourbon Trail , Cheerful 2 bedroom home, vacation rental in Waddy

Bourbon Trail , Cheerful 2 bedroom home

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Bagdad Bungalow on Bourbon Trail!  40 minutes from Valhalla, home to 2024 PGA!, vacation rental in Waddy
Bagdad Bungalow on Bourbon Trail!  40 minutes from Valhalla, home to 2024 PGA!, vacation rental in Waddy
Bagdad Bungalow on Bourbon Trail!  40 minutes from Valhalla, home to 2024 PGA!, vacation rental in Waddy

Bagdad Bungalow on Bourbon Trail! 40 minutes from Valhalla, home to 2024 PGA!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Bourbon Trail & Relaxing rural spot. Restored Farmhouse on 22 acres, all yours!, vacation rental in Waddy
Bourbon Trail & Relaxing rural spot. Restored Farmhouse on 22 acres, all yours!, vacation rental in Waddy
Bourbon Trail & Relaxing rural spot. Restored Farmhouse on 22 acres, all yours!, vacation rental in Waddy

Bourbon Trail & Relaxing rural spot. Restored Farmhouse on 22 acres, all yours!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Heritage House 1900’s home part/close to the Bourbon Trail, vacation rental in Waddy
Heritage House 1900’s home part/close to the Bourbon Trail, vacation rental in Waddy
Heritage House 1900’s home part/close to the Bourbon Trail, vacation rental in Waddy

Heritage House 1900’s home part/close to the Bourbon Trail

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Frankfort Home w/ 3 Balconies - 3 Mi to Downtown, vacation rental in Waddy
Frankfort Home w/ 3 Balconies - 3 Mi to Downtown, vacation rental in Waddy
Frankfort Home w/ 3 Balconies - 3 Mi to Downtown, vacation rental in Waddy

Frankfort Home w/ 3 Balconies - 3 Mi to Downtown

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Bourbon and Horse Racing, vacation rental in Waddy
Bourbon and Horse Racing, vacation rental in Waddy
Bourbon and Horse Racing, vacation rental in Waddy

Bourbon and Horse Racing

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill, vacation rental in Waddy
Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill, vacation rental in Waddy
Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill, vacation rental in Waddy

Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful, Peaceful Lakefront home in ❤️ of Bourbon Country in Shelbyville, KY, vacation rental in Waddy
Beautiful, Peaceful Lakefront home in ❤️ of Bourbon Country in Shelbyville, KY, vacation rental in Waddy
Beautiful, Peaceful Lakefront home in ❤️ of Bourbon Country in Shelbyville, KY, vacation rental in Waddy

Beautiful, Peaceful Lakefront home in ❤️ of Bourbon Country in Shelbyville, KY

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Peaceful, lakefront house on Guist Creek Lake/ Shelbyville-Bourbon Trail, vacation rental in Waddy
Peaceful, lakefront house on Guist Creek Lake/ Shelbyville-Bourbon Trail, vacation rental in Waddy
Peaceful, lakefront house on Guist Creek Lake/ Shelbyville-Bourbon Trail, vacation rental in Waddy

Peaceful, lakefront house on Guist Creek Lake/ Shelbyville-Bourbon Trail

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cabin+Bunkhouse Sleeps 25 near Lou/Lex *Like-New!, vacation rental in Waddy
Cabin+Bunkhouse Sleeps 25 near Lou/Lex *Like-New!, vacation rental in Waddy
Cabin+Bunkhouse Sleeps 25 near Lou/Lex *Like-New!, vacation rental in Waddy

Cabin+Bunkhouse Sleeps 25 near Lou/Lex *Like-New!

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 25
Match: Sleeps
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Bottled in Bond: Featured on HGTV, Close to Buffalo Trace, Sleeps 10., vacation rental in Waddy
Bottled in Bond: Featured on HGTV, Close to Buffalo Trace, Sleeps 10., vacation rental in Waddy
Bottled in Bond: Featured on HGTV, Close to Buffalo Trace, Sleeps 10., vacation rental in Waddy

Bottled in Bond: Featured on HGTV, Close to Buffalo Trace, Sleeps 10.

Condo/Apartment
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Stone Spring Farm situated in the center of Kentucky's Bourbon Country, vacation rental in Waddy
Stone Spring Farm situated in the center of Kentucky's Bourbon Country, vacation rental in Waddy
Stone Spring Farm situated in the center of Kentucky's Bourbon Country, vacation rental in Waddy

Stone Spring Farm situated in the center of Kentucky's Bourbon Country

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Urban Loft 5,000 SqFt. Sleeps 17 Next to Frankfort Distilleries,PERFECT LOCATION, vacation rental in Waddy
Urban Loft 5,000 SqFt. Sleeps 17 Next to Frankfort Distilleries,PERFECT LOCATION, vacation rental in Waddy
Urban Loft 5,000 SqFt. Sleeps 17 Next to Frankfort Distilleries,PERFECT LOCATION, vacation rental in Waddy

Urban Loft 5,000 SqFt. Sleeps 17 Next to Frankfort Distilleries,PERFECT LOCATION

Condo/Apartment
6 bedrooms
4 bathrooms
Sleeps 17
Match: Sleeps
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Saddlebred Suites 6 bed, 6 ba, vacation rental in Waddy
Saddlebred Suites 6 bed, 6 ba, vacation rental in Waddy
Saddlebred Suites 6 bed, 6 ba, vacation rental in Waddy

Saddlebred Suites 6 bed, 6 ba

Condo/Apartment
6 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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Spacious Home in the middle of horse and bourbon country!  Sleeps 8, firepit!!, vacation rental in Waddy
Spacious Home in the middle of horse and bourbon country!  Sleeps 8, firepit!!, vacation rental in Waddy
Spacious Home in the middle of horse and bourbon country!  Sleeps 8, firepit!!, vacation rental in Waddy

Spacious Home in the middle of horse and bourbon country! Sleeps 8, firepit!!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Gatsby and adjoining ceilings, vacation rental in Waddy
The Gatsby and adjoining ceilings, vacation rental in Waddy
The Gatsby and adjoining ceilings, vacation rental in Waddy

The Gatsby and adjoining ceilings

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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NEW! Mins to Distilleries! Hot tub, Game Room, Firepit, Luxury, Private 5-Acres!, vacation rental in Waddy
NEW! Mins to Distilleries! Hot tub, Game Room, Firepit, Luxury, Private 5-Acres!, vacation rental in Waddy
NEW! Mins to Distilleries! Hot tub, Game Room, Firepit, Luxury, Private 5-Acres!, vacation rental in Waddy

NEW! Mins to Distilleries! Hot tub, Game Room, Firepit, Luxury, Private 5-Acres!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Brand new, beautiful log cabin in the heart of bourbon and horse country., vacation rental in Waddy
Brand new, beautiful log cabin in the heart of bourbon and horse country., vacation rental in Waddy
Brand new, beautiful log cabin in the heart of bourbon and horse country., vacation rental in Waddy

Brand new, beautiful log cabin in the heart of bourbon and horse country.

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The Kentucky Bluegrass Retreat, vacation rental in Waddy
The Kentucky Bluegrass Retreat, vacation rental in Waddy
The Kentucky Bluegrass Retreat, vacation rental in Waddy

The Kentucky Bluegrass Retreat

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bourbon Trail Near Buffalo Trace-Hot Tub & Fire Pit, vacation rental in Waddy
Bourbon Trail Near Buffalo Trace-Hot Tub & Fire Pit, vacation rental in Waddy
Bourbon Trail Near Buffalo Trace-Hot Tub & Fire Pit, vacation rental in Waddy

Bourbon Trail Near Buffalo Trace-Hot Tub & Fire Pit

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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NEW: Hot Tub, Pool, Fully Loaded, 10 min to Bulleit, Between LOU and LEX., vacation rental in Waddy
NEW: Hot Tub, Pool, Fully Loaded, 10 min to Bulleit, Between LOU and LEX., vacation rental in Waddy
NEW: Hot Tub, Pool, Fully Loaded, 10 min to Bulleit, Between LOU and LEX., vacation rental in Waddy

NEW: Hot Tub, Pool, Fully Loaded, 10 min to Bulleit, Between LOU and LEX.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Encounter the Bluegrass & relax comfortably, vacation rental in Waddy
Encounter the Bluegrass & relax comfortably, vacation rental in Waddy
Encounter the Bluegrass & relax comfortably, vacation rental in Waddy

Encounter the Bluegrass & relax comfortably

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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New! Bourbon Trail Getaway: Fire Pit & Arcade Fun, vacation rental in Waddy
New! Bourbon Trail Getaway: Fire Pit & Arcade Fun, vacation rental in Waddy
New! Bourbon Trail Getaway: Fire Pit & Arcade Fun, vacation rental in Waddy

New! Bourbon Trail Getaway: Fire Pit & Arcade Fun

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby, vacation rental in Waddy
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby, vacation rental in Waddy
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby, vacation rental in Waddy

Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Hillside Cabin w/ Slps 20+ 11BD 3BA Fireplace & Hot Tub, vacation rental in Waddy
Hillside Cabin w/ Slps 20+ 11BD 3BA Fireplace & Hot Tub, vacation rental in Waddy
Hillside Cabin w/ Slps 20+ 11BD 3BA Fireplace & Hot Tub, vacation rental in Waddy

Hillside Cabin w/ Slps 20+ 11BD 3BA Fireplace & Hot Tub

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 20
Match: Sleeps
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Oakdale Farms! Fun game room! Hillside views, vacation rental in Waddy
Oakdale Farms! Fun game room! Hillside views, vacation rental in Waddy
Oakdale Farms! Fun game room! Hillside views, vacation rental in Waddy

Oakdale Farms! Fun game room! Hillside views

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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~ NEW HOT TUB�~ Bourbon Trail   ~ Golf⛳️~ Pool Table & Ping Pong �~ Cornhole~, vacation rental in Waddy
~ NEW HOT TUB�~ Bourbon Trail   ~ Golf⛳️~ Pool Table & Ping Pong �~ Cornhole~, vacation rental in Waddy
~ NEW HOT TUB�~ Bourbon Trail   ~ Golf⛳️~ Pool Table & Ping Pong �~ Cornhole~, vacation rental in Waddy

~ NEW HOT TUB�~ Bourbon Trail ~ Golf⛳️~ Pool Table & Ping Pong �~ Cornhole~

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Showing results 1-49 of 49
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