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Midway Vacation Rentals

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Bedrooms

Bathrooms

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5 mi
50 rentals in Midway.
Bourbon Trail, Horse Park & Farms, Keeneland, Vineyard & Winery, vacation rental in Midway
Bourbon Trail, Horse Park & Farms, Keeneland, Vineyard & Winery, vacation rental in Midway
Bourbon Trail, Horse Park & Farms, Keeneland, Vineyard & Winery, vacation rental in Midway

Bourbon Trail, Horse Park & Farms, Keeneland, Vineyard & Winery

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Convenient Townhome in the heart of horse and bourbon country!, vacation rental in Midway
Convenient Townhome in the heart of horse and bourbon country!, vacation rental in Midway
Convenient Townhome in the heart of horse and bourbon country!, vacation rental in Midway

Convenient Townhome in the heart of horse and bourbon country!

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Charming Cottage Conveniently Located In The Heart Of Horse And Bourbon Country, vacation rental in Midway
Charming Cottage Conveniently Located In The Heart Of Horse And Bourbon Country, vacation rental in Midway
Charming Cottage Conveniently Located In The Heart Of Horse And Bourbon Country, vacation rental in Midway

Charming Cottage Conveniently Located In The Heart Of Horse And Bourbon Country

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Elkhorn Creek Retreat, vacation rental in Midway
Elkhorn Creek Retreat, vacation rental in Midway
Elkhorn Creek Retreat, vacation rental in Midway

Elkhorn Creek Retreat

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful upstairs apartment located in historic downtown Midway, vacation rental in Midway
Beautiful upstairs apartment located in historic downtown Midway, vacation rental in Midway
Beautiful upstairs apartment located in historic downtown Midway, vacation rental in Midway

Beautiful upstairs apartment located in historic downtown Midway

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Modern Remodeled Downtown Midway Studio, vacation rental in Midway
Modern Remodeled Downtown Midway Studio, vacation rental in Midway
Modern Remodeled Downtown Midway Studio, vacation rental in Midway

Modern Remodeled Downtown Midway Studio

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Exclusive Spot in Downtown Midway, vacation rental in Midway
Exclusive Spot in Downtown Midway, vacation rental in Midway
Exclusive Spot in Downtown Midway, vacation rental in Midway

Exclusive Spot in Downtown Midway

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Railway House in Charming Downtown Midway, KY near Bourbon Trail/Keeneland, vacation rental in Midway
Railway House in Charming Downtown Midway, KY near Bourbon Trail/Keeneland, vacation rental in Midway
Railway House in Charming Downtown Midway, KY near Bourbon Trail/Keeneland, vacation rental in Midway

Railway House in Charming Downtown Midway, KY near Bourbon Trail/Keeneland

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Bit and Bourbon, vacation rental in Midway
Bit and Bourbon, vacation rental in Midway
Bit and Bourbon, vacation rental in Midway

Bit and Bourbon

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cozy cabin in the heart of horse country, vacation rental in Midway
Cozy cabin in the heart of horse country, vacation rental in Midway
Cozy cabin in the heart of horse country, vacation rental in Midway

Cozy cabin in the heart of horse country

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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This barn is a 2 bedroom(s), 1.5 bathrooms, located in Midway, KY., vacation rental in Midway
This barn is a 2 bedroom(s), 1.5 bathrooms, located in Midway, KY., vacation rental in Midway
This barn is a 2 bedroom(s), 1.5 bathrooms, located in Midway, KY., vacation rental in Midway

This barn is a 2 bedroom(s), 1.5 bathrooms, located in Midway, KY.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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KY Cottage -  Keeneland Horse Sales and Racing, KY Horse Park, Bourbon Tours, vacation rental in Midway
KY Cottage -  Keeneland Horse Sales and Racing, KY Horse Park, Bourbon Tours, vacation rental in Midway
KY Cottage -  Keeneland Horse Sales and Racing, KY Horse Park, Bourbon Tours, vacation rental in Midway

KY Cottage - Keeneland Horse Sales and Racing, KY Horse Park, Bourbon Tours

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Family-friendly newly built house in the heart of Kentucky's Horse Country, vacation rental in Midway
Family-friendly newly built house in the heart of Kentucky's Horse Country, vacation rental in Midway
Family-friendly newly built house in the heart of Kentucky's Horse Country, vacation rental in Midway

Family-friendly newly built house in the heart of Kentucky's Horse Country

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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HOLIDAY HOUSE - Kentucky Bluegrass Home on Champion Thoroughbred Farm, vacation rental in Midway
HOLIDAY HOUSE - Kentucky Bluegrass Home on Champion Thoroughbred Farm, vacation rental in Midway
HOLIDAY HOUSE - Kentucky Bluegrass Home on Champion Thoroughbred Farm, vacation rental in Midway

HOLIDAY HOUSE - Kentucky Bluegrass Home on Champion Thoroughbred Farm

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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The following properties within 20 miles of Midway match all your filters:
Charming Cottage Home On A Farm In The Kentucky Horse Country!  Relax!, vacation rental in Midway
Charming Cottage Home On A Farm In The Kentucky Horse Country!  Relax!, vacation rental in Midway
Charming Cottage Home On A Farm In The Kentucky Horse Country!  Relax!, vacation rental in Midway

Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Quiet-Country and Spacious Grandma's Duplex, vacation rental in Midway
Quiet-Country and Spacious Grandma's Duplex, vacation rental in Midway
Quiet-Country and Spacious Grandma's Duplex, vacation rental in Midway

Quiet-Country and Spacious Grandma's Duplex

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Jockey Suite at Sugar Hill Farm, vacation rental in Midway
Jockey Suite at Sugar Hill Farm, vacation rental in Midway
Jockey Suite at Sugar Hill Farm, vacation rental in Midway

Jockey Suite at Sugar Hill Farm

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Charming Cottage Home on Farm in Kentucky Horse Country!, vacation rental in Midway
Charming Cottage Home on Farm in Kentucky Horse Country!, vacation rental in Midway
Charming Cottage Home on Farm in Kentucky Horse Country!, vacation rental in Midway

Charming Cottage Home on Farm in Kentucky Horse Country!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Loft above Beautiful Horse Barn on Bourbon Trail, vacation rental in Midway
Loft above Beautiful Horse Barn on Bourbon Trail, vacation rental in Midway
Loft above Beautiful Horse Barn on Bourbon Trail, vacation rental in Midway

Loft above Beautiful Horse Barn on Bourbon Trail

Rental Home
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Linden Place is a new gated Cabin located in the middle of Bluegrass Horse Farms, vacation rental in Midway
Linden Place is a new gated Cabin located in the middle of Bluegrass Horse Farms, vacation rental in Midway
Linden Place is a new gated Cabin located in the middle of Bluegrass Horse Farms, vacation rental in Midway

Linden Place is a new gated Cabin located in the middle of Bluegrass Horse Farms

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Hidden Gem, vacation rental in Midway
Hidden Gem, vacation rental in Midway
Hidden Gem, vacation rental in Midway

Hidden Gem

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Stunning Horse Farm Experience on Bourbon Trail!, vacation rental in Midway
Stunning Horse Farm Experience on Bourbon Trail!, vacation rental in Midway
Stunning Horse Farm Experience on Bourbon Trail!, vacation rental in Midway

Stunning Horse Farm Experience on Bourbon Trail!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Charming 1930s home in the heart of horse country, vacation rental in Midway
Charming 1930s home in the heart of horse country, vacation rental in Midway
Charming 1930s home in the heart of horse country, vacation rental in Midway

Charming 1930s home in the heart of horse country

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Quiet, Comfortable Cottage, vacation rental in Midway
Quiet, Comfortable Cottage, vacation rental in Midway
Quiet, Comfortable Cottage, vacation rental in Midway

Quiet, Comfortable Cottage

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Springwood Cottage in the Heart of the Bluegrass, vacation rental in Midway
Springwood Cottage in the Heart of the Bluegrass, vacation rental in Midway
Springwood Cottage in the Heart of the Bluegrass, vacation rental in Midway

Springwood Cottage in the Heart of the Bluegrass

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Lakehouse on the  KY Bourbon Trail - Pet Friendly, vacation rental in Midway
Lakehouse on the  KY Bourbon Trail - Pet Friendly, vacation rental in Midway
Lakehouse on the  KY Bourbon Trail - Pet Friendly, vacation rental in Midway

Lakehouse on the KY Bourbon Trail - Pet Friendly

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Five Minutes from Keeneland!, vacation rental in Midway
Five Minutes from Keeneland!, vacation rental in Midway
Five Minutes from Keeneland!, vacation rental in Midway

Five Minutes from Keeneland!

Rental Home
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Four Roses Unit, The Woodford Hotel, vacation rental in Midway
Four Roses Unit, The Woodford Hotel, vacation rental in Midway
Four Roses Unit, The Woodford Hotel, vacation rental in Midway

Four Roses Unit, The Woodford Hotel

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Golf Course , Bourbon And Horses!!  Apt near Horse Park and the Bourbon Trail, vacation rental in Midway
Golf Course , Bourbon And Horses!!  Apt near Horse Park and the Bourbon Trail, vacation rental in Midway
Golf Course , Bourbon And Horses!!  Apt near Horse Park and the Bourbon Trail, vacation rental in Midway

Golf Course , Bourbon And Horses!! Apt near Horse Park and the Bourbon Trail

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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EH Taylor Unit, The Woodford Hotel, vacation rental in Midway
EH Taylor Unit, The Woodford Hotel, vacation rental in Midway
EH Taylor Unit, The Woodford Hotel, vacation rental in Midway

EH Taylor Unit, The Woodford Hotel

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Condo unit #5 on Longview Golf Club, vacation rental in Midway
Condo unit #5 on Longview Golf Club, vacation rental in Midway
Condo unit #5 on Longview Golf Club, vacation rental in Midway

Condo unit #5 on Longview Golf Club

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Condo Unit #9 on Longview Golf Club, vacation rental in Midway
Condo Unit #9 on Longview Golf Club, vacation rental in Midway
Condo Unit #9 on Longview Golf Club, vacation rental in Midway

Condo Unit #9 on Longview Golf Club

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Condo Unit #6 on Longview Golf Club, vacation rental in Midway
Condo Unit #6 on Longview Golf Club, vacation rental in Midway
Condo Unit #6 on Longview Golf Club, vacation rental in Midway

Condo Unit #6 on Longview Golf Club

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Pappy VanWinkle Unit, The Woodford Hotel, vacation rental in Midway
Pappy VanWinkle Unit, The Woodford Hotel, vacation rental in Midway
Pappy VanWinkle Unit, The Woodford Hotel, vacation rental in Midway

Pappy VanWinkle Unit, The Woodford Hotel

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Buffalo Trace Blantons Distillery Historic Dwntwn, vacation rental in Midway
Buffalo Trace Blantons Distillery Historic Dwntwn, vacation rental in Midway
Buffalo Trace Blantons Distillery Historic Dwntwn, vacation rental in Midway

Buffalo Trace Blantons Distillery Historic Dwntwn

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Sugar Hill Farm- Pool/9 Guests/10min to Airport, vacation rental in Midway
Sugar Hill Farm- Pool/9 Guests/10min to Airport, vacation rental in Midway
Sugar Hill Farm- Pool/9 Guests/10min to Airport, vacation rental in Midway

Sugar Hill Farm- Pool/9 Guests/10min to Airport

Condo/Apartment
0 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
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House near ky horse park, vacation rental in Midway
House near ky horse park, vacation rental in Midway
House near ky horse park, vacation rental in Midway

House near ky horse park

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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"The Guest House", Located on a 300 acre horse farm., vacation rental in Midway
"The Guest House", Located on a 300 acre horse farm., vacation rental in Midway
"The Guest House", Located on a 300 acre horse farm., vacation rental in Midway

"The Guest House", Located on a 300 acre horse farm.

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Quiet Two Bedroom House, vacation rental in Midway
Quiet Two Bedroom House, vacation rental in Midway
Quiet Two Bedroom House, vacation rental in Midway

Quiet Two Bedroom House

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Wild Turkey - Buffalo Trace - Historic Distillery, vacation rental in Midway
Wild Turkey - Buffalo Trace - Historic Distillery, vacation rental in Midway
Wild Turkey - Buffalo Trace - Historic Distillery, vacation rental in Midway

Wild Turkey - Buffalo Trace - Historic Distillery

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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My Old Kentucky Home3 bedroom, 2 full bath. Sleeps 7, vacation rental in Midway
My Old Kentucky Home3 bedroom, 2 full bath. Sleeps 7, vacation rental in Midway
My Old Kentucky Home3 bedroom, 2 full bath. Sleeps 7, vacation rental in Midway

My Old Kentucky Home3 bedroom, 2 full bath. Sleeps 7

Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Paynes Landing Cozy Getaway, vacation rental in Midway
Paynes Landing Cozy Getaway, vacation rental in Midway
Paynes Landing Cozy Getaway, vacation rental in Midway

Paynes Landing Cozy Getaway

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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3 miles from the Ky Horse Park. Read the house rules and listing before you book, vacation rental in Midway
3 miles from the Ky Horse Park. Read the house rules and listing before you book, vacation rental in Midway
3 miles from the Ky Horse Park. Read the house rules and listing before you book, vacation rental in Midway

3 miles from the Ky Horse Park. Read the house rules and listing before you book

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Stunning Home on 125ac farm in Bourbon & Horse country. 20% OFF Oct/Nov weekly, vacation rental in Midway
Stunning Home on 125ac farm in Bourbon & Horse country. 20% OFF Oct/Nov weekly, vacation rental in Midway
Stunning Home on 125ac farm in Bourbon & Horse country. 20% OFF Oct/Nov weekly, vacation rental in Midway

Stunning Home on 125ac farm in Bourbon & Horse country. 20% OFF Oct/Nov weekly

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Equestrian Elegance Tranquil Retreat Horse Bourbon, vacation rental in Midway
Equestrian Elegance Tranquil Retreat Horse Bourbon, vacation rental in Midway
Equestrian Elegance Tranquil Retreat Horse Bourbon, vacation rental in Midway

Equestrian Elegance Tranquil Retreat Horse Bourbon

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Elmcrest Farm 1B Lexington Guest Apartment -Main House VRBO 3581789, vacation rental in Midway
Elmcrest Farm 1B Lexington Guest Apartment -Main House VRBO 3581789, vacation rental in Midway
Elmcrest Farm 1B Lexington Guest Apartment -Main House VRBO 3581789, vacation rental in Midway

Elmcrest Farm 1B Lexington Guest Apartment -Main House VRBO 3581789

Condo/Apartment
4 bedrooms
5 bathrooms
Sleeps 4
Match: Sleeps
More info
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Elmcrest Farm 3B/3B Lexington Home  - Opt. 1B/1B Separate Apt., vacation rental in Midway
Elmcrest Farm 3B/3B Lexington Home  - Opt. 1B/1B Separate Apt., vacation rental in Midway
Elmcrest Farm 3B/3B Lexington Home  - Opt. 1B/1B Separate Apt., vacation rental in Midway

Elmcrest Farm 3B/3B Lexington Home - Opt. 1B/1B Separate Apt.

Rental Home
4 bedrooms
5 bathrooms
Sleeps 6
Match: Sleeps
More info
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Queenslake Mansion and Horse Farm, vacation rental in Midway
Queenslake Mansion and Horse Farm, vacation rental in Midway
Queenslake Mansion and Horse Farm, vacation rental in Midway

Queenslake Mansion and Horse Farm

Rental Home
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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This circa 1917 house has been given new life with a thoughtful renovation by, vacation rental in Midway
This circa 1917 house has been given new life with a thoughtful renovation by, vacation rental in Midway
This circa 1917 house has been given new life with a thoughtful renovation by, vacation rental in Midway

This circa 1917 house has been given new life with a thoughtful renovation by

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Historic Woodford Buffalo Trace Distil - Sleeps 24, vacation rental in Midway
Historic Woodford Buffalo Trace Distil - Sleeps 24, vacation rental in Midway
Historic Woodford Buffalo Trace Distil - Sleeps 24, vacation rental in Midway

Historic Woodford Buffalo Trace Distil - Sleeps 24

Rental Home
10 bedrooms
10 bathrooms
Sleeps 24
Match: Sleeps
More info
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Showing results 1-50 of 50
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