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Lexington Holiday Apartments

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137 rentals in Lexington.
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Luxury Updated Chevy Chase Home - Close to UK, holiday rental in Lexington
Luxury Updated Chevy Chase Home - Close to UK, holiday rental in Lexington
Luxury Updated Chevy Chase Home - Close to UK, holiday rental in Lexington

Luxury Updated Chevy Chase Home - Close to UK

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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3 Bdr/3 Bath House in Andover Convenient to All of Lexington, holiday rental in Lexington
3 Bdr/3 Bath House in Andover Convenient to All of Lexington, holiday rental in Lexington
3 Bdr/3 Bath House in Andover Convenient to All of Lexington, holiday rental in Lexington

3 Bdr/3 Bath House in Andover Convenient to All of Lexington

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Historic Mansion in Downtown Lexington., holiday rental in Lexington
Historic Mansion in Downtown Lexington., holiday rental in Lexington
Historic Mansion in Downtown Lexington., holiday rental in Lexington

Historic Mansion in Downtown Lexington.

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Charming Cottage Home On A Farm In The Kentucky Horse Country!  Relax!, holiday rental in Lexington
Charming Cottage Home On A Farm In The Kentucky Horse Country!  Relax!, holiday rental in Lexington
Charming Cottage Home On A Farm In The Kentucky Horse Country!  Relax!, holiday rental in Lexington

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cottage on working Thoroughbred Horse Farm on Kentucky's Horse Parkway, holiday rental in Lexington
Cottage on working Thoroughbred Horse Farm on Kentucky's Horse Parkway, holiday rental in Lexington
Cottage on working Thoroughbred Horse Farm on Kentucky's Horse Parkway, holiday rental in Lexington

Cottage on working Thoroughbred Horse Farm on Kentucky's Horse Parkway

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location, holiday rental in Lexington
Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location, holiday rental in Lexington
Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location, holiday rental in Lexington

Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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The Martin House - In the heart of historic downtown Lexington, holiday rental in Lexington
The Martin House - In the heart of historic downtown Lexington, holiday rental in Lexington
The Martin House - In the heart of historic downtown Lexington, holiday rental in Lexington

The Martin House - In the heart of historic downtown Lexington

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Historic Brick Cottage w/carriage house downtown Lexington sleeps 8, holiday rental in Lexington
Historic Brick Cottage w/carriage house downtown Lexington sleeps 8, holiday rental in Lexington
Historic Brick Cottage w/carriage house downtown Lexington sleeps 8, holiday rental in Lexington

Historic Brick Cottage w/carriage house downtown Lexington sleeps 8

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Cottage on horse farm close to Keeneland, Airport, Horse Park, Bourbon Trail, holiday rental in Lexington
Cottage on horse farm close to Keeneland, Airport, Horse Park, Bourbon Trail, holiday rental in Lexington
Cottage on horse farm close to Keeneland, Airport, Horse Park, Bourbon Trail, holiday rental in Lexington

Cottage on horse farm close to Keeneland, Airport, Horse Park, Bourbon Trail

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cheerful and Cozy in the Heart of Chevy Chase!, holiday rental in Lexington
Cheerful and Cozy in the Heart of Chevy Chase!, holiday rental in Lexington
Cheerful and Cozy in the Heart of Chevy Chase!, holiday rental in Lexington

Cheerful and Cozy in the Heart of Chevy Chase!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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A hidden gem in Lexington's Historic District, holiday rental in Lexington
A hidden gem in Lexington's Historic District, holiday rental in Lexington
A hidden gem in Lexington's Historic District, holiday rental in Lexington

A hidden gem in Lexington's Historic District

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Guest House on Kentucky Working Thoroughbred Horse Farm, holiday rental in Lexington
Guest House on Kentucky Working Thoroughbred Horse Farm, holiday rental in Lexington
Guest House on Kentucky Working Thoroughbred Horse Farm, holiday rental in Lexington

Guest House on Kentucky Working Thoroughbred Horse Farm

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Perfect for Summer! Close to downtown & surrounding area attractions!, holiday rental in Lexington
Perfect for Summer! Close to downtown & surrounding area attractions!, holiday rental in Lexington
Perfect for Summer! Close to downtown & surrounding area attractions!, holiday rental in Lexington

Perfect for Summer! Close to downtown & surrounding area attractions!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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World Class Horse Farm Minutes To Keeneland, Bluegrass Airport, Bourbon Trail, holiday rental in Lexington
World Class Horse Farm Minutes To Keeneland, Bluegrass Airport, Bourbon Trail, holiday rental in Lexington
World Class Horse Farm Minutes To Keeneland, Bluegrass Airport, Bourbon Trail, holiday rental in Lexington

World Class Horse Farm Minutes To Keeneland, Bluegrass Airport, Bourbon Trail

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Luxury 5BR/4BA Updated Home In The Heart Of Lexington, holiday rental in Lexington
Luxury 5BR/4BA Updated Home In The Heart Of Lexington, holiday rental in Lexington
Luxury 5BR/4BA Updated Home In The Heart Of Lexington, holiday rental in Lexington

Luxury 5BR/4BA Updated Home In The Heart Of Lexington

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Beautiful country house with pool 10  minutes from Lexington, holiday rental in Lexington
Beautiful country house with pool 10  minutes from Lexington, holiday rental in Lexington
Beautiful country house with pool 10  minutes from Lexington, holiday rental in Lexington

Beautiful country house with pool 10 minutes from Lexington

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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The Wine Cellar Condominium, holiday rental in Lexington
The Wine Cellar Condominium, holiday rental in Lexington
The Wine Cellar Condominium, holiday rental in Lexington

The Wine Cellar Condominium

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Private Lake/Farm Retreat, holiday rental in Lexington
Private Lake/Farm Retreat, holiday rental in Lexington
Private Lake/Farm Retreat, holiday rental in Lexington

Private Lake/Farm Retreat

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Comfortable Family Home, holiday rental in Lexington
Comfortable Family Home, holiday rental in Lexington
Comfortable Family Home, holiday rental in Lexington

Comfortable Family Home

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
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Charming Historic Home in Downtown Lexington, holiday rental in Lexington
Charming Historic Home in Downtown Lexington, holiday rental in Lexington
Charming Historic Home in Downtown Lexington, holiday rental in Lexington

Charming Historic Home in Downtown Lexington

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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KY Horse Park, Equestrian Events, Derby, Keeneland!  4 miles off I-75/I-64, holiday rental in Lexington
KY Horse Park, Equestrian Events, Derby, Keeneland!  4 miles off I-75/I-64, holiday rental in Lexington
KY Horse Park, Equestrian Events, Derby, Keeneland!  4 miles off I-75/I-64, holiday rental in Lexington

KY Horse Park, Equestrian Events, Derby, Keeneland! 4 miles off I-75/I-64

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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Kentucky River Cottages ~ Featured on the Live Well Network's Sweet Retreats!, holiday rental in Lexington
Kentucky River Cottages ~ Featured on the Live Well Network's Sweet Retreats!, holiday rental in Lexington
Kentucky River Cottages ~ Featured on the Live Well Network's Sweet Retreats!, holiday rental in Lexington

Kentucky River Cottages ~ Featured on the Live Well Network's Sweet Retreats!

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Brand New Cottage, 1 mile from Keeneland, holiday rental in Lexington
Brand New Cottage, 1 mile from Keeneland, holiday rental in Lexington
Brand New Cottage, 1 mile from Keeneland, holiday rental in Lexington

Brand New Cottage, 1 mile from Keeneland

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lexington Apt. with parking & private entrance Preview listing, holiday rental in Lexington
Lexington Apt. with parking & private entrance Preview listing, holiday rental in Lexington
Lexington Apt. with parking & private entrance Preview listing, holiday rental in Lexington

Lexington Apt. with parking & private entrance Preview listing

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Elegant Equestrian-Themed Home Minutes From Keeneland, Airport & Restaurants, holiday rental in Lexington
Elegant Equestrian-Themed Home Minutes From Keeneland, Airport & Restaurants, holiday rental in Lexington
Elegant Equestrian-Themed Home Minutes From Keeneland, Airport & Restaurants, holiday rental in Lexington

Elegant Equestrian-Themed Home Minutes From Keeneland, Airport & Restaurants

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Paradiso - Divine Condo, Perfect Location Walkable to Everything Downtown, holiday rental in Lexington
Paradiso - Divine Condo, Perfect Location Walkable to Everything Downtown, holiday rental in Lexington
Paradiso - Divine Condo, Perfect Location Walkable to Everything Downtown, holiday rental in Lexington

Paradiso - Divine Condo, Perfect Location Walkable to Everything Downtown

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Completely refurbished downstairs apartment in 1920's home, holiday rental in Lexington
Completely refurbished downstairs apartment in 1920's home, holiday rental in Lexington
Completely refurbished downstairs apartment in 1920's home, holiday rental in Lexington

Completely refurbished downstairs apartment in 1920's home

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Private Apartment in Downtown Lexington, holiday rental in Lexington
Private Apartment in Downtown Lexington, holiday rental in Lexington
Private Apartment in Downtown Lexington, holiday rental in Lexington

Private Apartment in Downtown Lexington

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Kentucky Bourbon Suite, holiday rental in Lexington
The Kentucky Bourbon Suite, holiday rental in Lexington
The Kentucky Bourbon Suite, holiday rental in Lexington

The Kentucky Bourbon Suite

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Modern & Elegant Carriage House at Historic Warsaw, holiday rental in Lexington
Modern & Elegant Carriage House at Historic Warsaw, holiday rental in Lexington
Modern & Elegant Carriage House at Historic Warsaw, holiday rental in Lexington

Modern & Elegant Carriage House at Historic Warsaw

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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3,500 sq ft with All New Furnishings + Green Space, holiday rental in Lexington
3,500 sq ft with All New Furnishings + Green Space, holiday rental in Lexington
3,500 sq ft with All New Furnishings + Green Space, holiday rental in Lexington

3,500 sq ft with All New Furnishings + Green Space

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena and Alltech, holiday rental in Lexington
Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena and Alltech, holiday rental in Lexington
Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena and Alltech, holiday rental in Lexington

Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena and Alltech

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Renovated Downtown Lexington Apartment, holiday rental in Lexington
Renovated Downtown Lexington Apartment, holiday rental in Lexington
Renovated Downtown Lexington Apartment, holiday rental in Lexington

Renovated Downtown Lexington Apartment

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming Kentucky Cottage, holiday rental in Lexington
Charming Kentucky Cottage, holiday rental in Lexington
Charming Kentucky Cottage, holiday rental in Lexington

Charming Kentucky Cottage

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Downtown Townhome Near Rupp Arena, holiday rental in Lexington
Downtown Townhome Near Rupp Arena, holiday rental in Lexington
Downtown Townhome Near Rupp Arena, holiday rental in Lexington

Downtown Townhome Near Rupp Arena

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Springwood Cottage in the Heart of the Bluegrass, holiday rental in Lexington
Springwood Cottage in the Heart of the Bluegrass, holiday rental in Lexington
Springwood Cottage in the Heart of the Bluegrass, holiday rental in Lexington

Springwood Cottage in the Heart of the Bluegrass

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Unique Stay in a 1907 Log Cabin on The Kentucky River, holiday rental in Lexington
Unique Stay in a 1907 Log Cabin on The Kentucky River, holiday rental in Lexington
Unique Stay in a 1907 Log Cabin on The Kentucky River, holiday rental in Lexington

Unique Stay in a 1907 Log Cabin on The Kentucky River

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Brand New Remodel with Private Backyard! 1 minute walk to dining and retail!, holiday rental in Lexington
Brand New Remodel with Private Backyard! 1 minute walk to dining and retail!, holiday rental in Lexington
Brand New Remodel with Private Backyard! 1 minute walk to dining and retail!, holiday rental in Lexington

Brand New Remodel with Private Backyard! 1 minute walk to dining and retail!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Bourbon Country's Clubhouse Year Round Pool Estate, holiday rental in Lexington
Bourbon Country's Clubhouse Year Round Pool Estate, holiday rental in Lexington
Bourbon Country's Clubhouse Year Round Pool Estate, holiday rental in Lexington

Bourbon Country's Clubhouse Year Round Pool Estate

Holiday Rental House
8 bedrooms
11 bathrooms
Sleeps 40
Match: Sleeps
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NEW! Horse Farm Hideaway ~ 6 Mi to KY Horse Park!, holiday rental in Lexington
NEW! Horse Farm Hideaway ~ 6 Mi to KY Horse Park!, holiday rental in Lexington
NEW! Horse Farm Hideaway ~ 6 Mi to KY Horse Park!, holiday rental in Lexington

NEW! Horse Farm Hideaway ~ 6 Mi to KY Horse Park!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Newly remodeled home central to downtown!, holiday rental in Lexington
Newly remodeled home central to downtown!, holiday rental in Lexington
Newly remodeled home central to downtown!, holiday rental in Lexington

Newly remodeled home central to downtown!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Top Shelf Condo!  For Explorers Seeking An Exclusive Kentucky Experience, holiday rental in Lexington
The Top Shelf Condo!  For Explorers Seeking An Exclusive Kentucky Experience, holiday rental in Lexington
The Top Shelf Condo!  For Explorers Seeking An Exclusive Kentucky Experience, holiday rental in Lexington

The Top Shelf Condo! For Explorers Seeking An Exclusive Kentucky Experience

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Your Home Away From Home, holiday rental in Lexington
Your Home Away From Home, holiday rental in Lexington
Your Home Away From Home, holiday rental in Lexington

Your Home Away From Home

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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NEW Luxury Remodel 4BR/2.5BA Only 10 min to Keeneland and downtown, holiday rental in Lexington
NEW Luxury Remodel 4BR/2.5BA Only 10 min to Keeneland and downtown, holiday rental in Lexington
NEW Luxury Remodel 4BR/2.5BA Only 10 min to Keeneland and downtown, holiday rental in Lexington

NEW Luxury Remodel 4BR/2.5BA Only 10 min to Keeneland and downtown

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Upscale downtown Lexington townhome, holiday rental in Lexington
Upscale downtown Lexington townhome, holiday rental in Lexington
Upscale downtown Lexington townhome, holiday rental in Lexington

Upscale downtown Lexington townhome

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Historic Downtown Private Room and Bath, holiday rental in Lexington
Historic Downtown Private Room and Bath, holiday rental in Lexington
Historic Downtown Private Room and Bath, holiday rental in Lexington

Historic Downtown Private Room and Bath

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Town home with private garage and backyard, holiday rental in Lexington
Town home with private garage and backyard, holiday rental in Lexington
Town home with private garage and backyard, holiday rental in Lexington

Town home with private garage and backyard

Holiday Rental House
1 bedroom
3 bathrooms
Sleeps 2
Match: Sleeps
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The Black Bear Lodge, holiday rental in Lexington
The Black Bear Lodge, holiday rental in Lexington
The Black Bear Lodge, holiday rental in Lexington

The Black Bear Lodge

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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1.7 miles to KY Horse Park, holiday rental in Lexington
1.7 miles to KY Horse Park, holiday rental in Lexington
1.7 miles to KY Horse Park, holiday rental in Lexington

1.7 miles to KY Horse Park

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Kentucky River Cottages ~ 3rd Floor Suite ~ On The Bourbon Trail!, holiday rental in Lexington
Kentucky River Cottages ~ 3rd Floor Suite ~ On The Bourbon Trail!, holiday rental in Lexington
Kentucky River Cottages ~ 3rd Floor Suite ~ On The Bourbon Trail!, holiday rental in Lexington

Kentucky River Cottages ~ 3rd Floor Suite ~ On The Bourbon Trail!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Frequently Asked Questions about Lexington