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Winchester Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
50 rentals in Winchester.
Family and Friends at Franklin Ridge Farms, vacation rental in Winchester
Family and Friends at Franklin Ridge Farms, vacation rental in Winchester
Family and Friends at Franklin Ridge Farms, vacation rental in Winchester

Family and Friends at Franklin Ridge Farms

Rental Home
4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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2nd Story Historic Downtown 2BR with Modern Amenities, vacation rental in Winchester
2nd Story Historic Downtown 2BR with Modern Amenities, vacation rental in Winchester
2nd Story Historic Downtown 2BR with Modern Amenities, vacation rental in Winchester

2nd Story Historic Downtown 2BR with Modern Amenities

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Large Downtown Artist's Loft, 30 min to Lexington, Horse, Bourbon, R River Gorge, vacation rental in Winchester
Large Downtown Artist's Loft, 30 min to Lexington, Horse, Bourbon, R River Gorge, vacation rental in Winchester
Large Downtown Artist's Loft, 30 min to Lexington, Horse, Bourbon, R River Gorge, vacation rental in Winchester

Large Downtown Artist's Loft, 30 min to Lexington, Horse, Bourbon, R River Gorge

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Country getaway, vacation rental in Winchester
Country getaway, vacation rental in Winchester
Country getaway, vacation rental in Winchester

Country getaway

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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This house is a 3 bedroom(s), 2 bathrooms, located in Winchester, KY., vacation rental in Winchester
This house is a 3 bedroom(s), 2 bathrooms, located in Winchester, KY., vacation rental in Winchester
This house is a 3 bedroom(s), 2 bathrooms, located in Winchester, KY., vacation rental in Winchester

This house is a 3 bedroom(s), 2 bathrooms, located in Winchester, KY.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Historic Log Cabin - Farm - Near RRG, The Barnyard Music Venue and Lexington, vacation rental in Winchester
Historic Log Cabin - Farm - Near RRG, The Barnyard Music Venue and Lexington, vacation rental in Winchester
Historic Log Cabin - Farm - Near RRG, The Barnyard Music Venue and Lexington, vacation rental in Winchester

Historic Log Cabin - Farm - Near RRG, The Barnyard Music Venue and Lexington

Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Farmhouse living within sight of Lexington - Horse Paddock available, vacation rental in Winchester
Farmhouse living within sight of Lexington - Horse Paddock available, vacation rental in Winchester
Farmhouse living within sight of Lexington - Horse Paddock available, vacation rental in Winchester

Farmhouse living within sight of Lexington - Horse Paddock available

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Camper at Old Pine Grove, vacation rental in Winchester
Cozy Camper at Old Pine Grove, vacation rental in Winchester
Cozy Camper at Old Pine Grove, vacation rental in Winchester

Cozy Camper at Old Pine Grove

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The following properties within 20 miles of Winchester match all your filters:
Beautiful cabin minutes from Red River Gorge, vacation rental in Winchester
Beautiful cabin minutes from Red River Gorge, vacation rental in Winchester
Beautiful cabin minutes from Red River Gorge, vacation rental in Winchester

Beautiful cabin minutes from Red River Gorge

Rental Home
1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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3 Bdr/3 Bath House in Andover Convenient to All of Lexington, vacation rental in Winchester
3 Bdr/3 Bath House in Andover Convenient to All of Lexington, vacation rental in Winchester
3 Bdr/3 Bath House in Andover Convenient to All of Lexington, vacation rental in Winchester

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Renovated Train Station on Thoroughbred Horse Farm, vacation rental in Winchester
Renovated Train Station on Thoroughbred Horse Farm, vacation rental in Winchester
Renovated Train Station on Thoroughbred Horse Farm, vacation rental in Winchester

Renovated Train Station on Thoroughbred Horse Farm

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Hot Tub, WiFi, Pet-Friendly - Cozy Tiny Cabin - The Ridge at Red River Gorge, vacation rental in Winchester
Hot Tub, WiFi, Pet-Friendly - Cozy Tiny Cabin - The Ridge at Red River Gorge, vacation rental in Winchester
Hot Tub, WiFi, Pet-Friendly - Cozy Tiny Cabin - The Ridge at Red River Gorge, vacation rental in Winchester

Hot Tub, WiFi, Pet-Friendly - Cozy Tiny Cabin - The Ridge at Red River Gorge

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cute Crib with Wide Screen Home Theater and Games, vacation rental in Winchester
Cute Crib with Wide Screen Home Theater and Games, vacation rental in Winchester
Cute Crib with Wide Screen Home Theater and Games, vacation rental in Winchester

Cute Crib with Wide Screen Home Theater and Games

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Right off interstate - sleeping for 14 -next to best shopping and dinning in Lex, vacation rental in Winchester
Right off interstate - sleeping for 14 -next to best shopping and dinning in Lex, vacation rental in Winchester
Right off interstate - sleeping for 14 -next to best shopping and dinning in Lex, vacation rental in Winchester

Right off interstate - sleeping for 14 -next to best shopping and dinning in Lex

Rental Home
5 bedrooms
4 bathrooms
Sleeps 18
Match: Sleeps
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2 Bed/2 Bath Home in Andover area. Premier Host with 250+ 5-Star Reviews!, vacation rental in Winchester
2 Bed/2 Bath Home in Andover area. Premier Host with 250+ 5-Star Reviews!, vacation rental in Winchester
2 Bed/2 Bath Home in Andover area. Premier Host with 250+ 5-Star Reviews!, vacation rental in Winchester

2 Bed/2 Bath Home in Andover area. Premier Host with 250+ 5-Star Reviews!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Hamburg Haven / Garage /� Pit / 7mi to Rupp / WiFi, vacation rental in Winchester
Hamburg Haven / Garage /� Pit / 7mi to Rupp / WiFi, vacation rental in Winchester
Hamburg Haven / Garage /� Pit / 7mi to Rupp / WiFi, vacation rental in Winchester

Hamburg Haven / Garage /� Pit / 7mi to Rupp / WiFi

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Hamburg Retreat: Firepit, Walking Trail, Shopping, Dining, Entertainment & More, vacation rental in Winchester
Hamburg Retreat: Firepit, Walking Trail, Shopping, Dining, Entertainment & More, vacation rental in Winchester
Hamburg Retreat: Firepit, Walking Trail, Shopping, Dining, Entertainment & More, vacation rental in Winchester

Hamburg Retreat: Firepit, Walking Trail, Shopping, Dining, Entertainment & More

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Peaceful Mt Sterling Cabin: Deck & Fire Pit!, vacation rental in Winchester
Peaceful Mt Sterling Cabin: Deck & Fire Pit!, vacation rental in Winchester
Peaceful Mt Sterling Cabin: Deck & Fire Pit!, vacation rental in Winchester

Peaceful Mt Sterling Cabin: Deck & Fire Pit!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Colliver House at Claybank Farm, vacation rental in Winchester
Colliver House at Claybank Farm, vacation rental in Winchester
Colliver House at Claybank Farm, vacation rental in Winchester

Colliver House at Claybank Farm

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Renovated train station on thoroughbred horse farm., vacation rental in Winchester
Renovated train station on thoroughbred horse farm., vacation rental in Winchester
Renovated train station on thoroughbred horse farm., vacation rental in Winchester

Renovated train station on thoroughbred horse farm.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cabin in Kentucky Horse Country, vacation rental in Winchester
Cabin in Kentucky Horse Country, vacation rental in Winchester
Cabin in Kentucky Horse Country, vacation rental in Winchester

Cabin in Kentucky Horse Country

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY, vacation rental in Winchester
Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY, vacation rental in Winchester
Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY, vacation rental in Winchester

Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Comfort and Convenience! Free Breakfast, Free Parking, Close to Loudoun House, vacation rental in Winchester
Comfort and Convenience! Free Breakfast, Free Parking, Close to Loudoun House, vacation rental in Winchester
Comfort and Convenience! Free Breakfast, Free Parking, Close to Loudoun House, vacation rental in Winchester

Comfort and Convenience! Free Breakfast, Free Parking, Close to Loudoun House

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Boone Creek Lodge and Troutfishing in Lexington KY, vacation rental in Winchester
Boone Creek Lodge and Troutfishing in Lexington KY, vacation rental in Winchester
Boone Creek Lodge and Troutfishing in Lexington KY, vacation rental in Winchester

Boone Creek Lodge and Troutfishing in Lexington KY

Rental Home
4 bedrooms
4 bathrooms
Sleeps 17
Match: Sleeps
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'Edith' Carriage House Getaway - I-75/Hamburg!, vacation rental in Winchester
'Edith' Carriage House Getaway - I-75/Hamburg!, vacation rental in Winchester
'Edith' Carriage House Getaway - I-75/Hamburg!, vacation rental in Winchester

'Edith' Carriage House Getaway - I-75/Hamburg!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cabin on I-75 in Lexington an Outdoor Destination, vacation rental in Winchester
Cabin on I-75 in Lexington an Outdoor Destination, vacation rental in Winchester
Cabin on I-75 in Lexington an Outdoor Destination, vacation rental in Winchester

Cabin on I-75 in Lexington an Outdoor Destination

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Kentucky River Cottages ~ 3rd Floor Suite ~ On The Bourbon Trail!, vacation rental in Winchester
Kentucky River Cottages ~ 3rd Floor Suite ~ On The Bourbon Trail!, vacation rental in Winchester
Kentucky River Cottages ~ 3rd Floor Suite ~ On The Bourbon Trail!, vacation rental in Winchester

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

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Budget-Friendly Property, Free Breakfast, Onsite Pool, Free Parking, vacation rental in Winchester
Budget-Friendly Property, Free Breakfast, Onsite Pool, Free Parking, vacation rental in Winchester
Budget-Friendly Property, Free Breakfast, Onsite Pool, Free Parking, vacation rental in Winchester

Budget-Friendly Property, Free Breakfast, Onsite Pool, Free Parking

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Budget-Friendly Property, Free Breakfast, Free Parking, Onsite Pool, vacation rental in Winchester
Budget-Friendly Property, Free Breakfast, Free Parking, Onsite Pool, vacation rental in Winchester
Budget-Friendly Property, Free Breakfast, Free Parking, Onsite Pool, vacation rental in Winchester

Budget-Friendly Property, Free Breakfast, Free Parking, Onsite Pool

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Your Home Away From Home! Free Breakfast, Free Parking, Near Applebee s Park, vacation rental in Winchester
Your Home Away From Home! Free Breakfast, Free Parking, Near Applebee s Park, vacation rental in Winchester
Your Home Away From Home! Free Breakfast, Free Parking, Near Applebee s Park, vacation rental in Winchester

Your Home Away From Home! Free Breakfast, Free Parking, Near Applebee s Park

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Historic 2-Bedroom in Downtown, vacation rental in Winchester
Historic 2-Bedroom in Downtown, vacation rental in Winchester
Historic 2-Bedroom in Downtown, vacation rental in Winchester

Historic 2-Bedroom in Downtown

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Unique Stay in a 1907 Log Cabin on The Kentucky River, vacation rental in Winchester
Unique Stay in a 1907 Log Cabin on The Kentucky River, vacation rental in Winchester
Unique Stay in a 1907 Log Cabin on The Kentucky River, vacation rental in Winchester

Unique Stay in a 1907 Log Cabin on The Kentucky River

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Honey Hut, Think of “ On Golden Pond", vacation rental in Winchester
The Honey Hut, Think of “ On Golden Pond", vacation rental in Winchester
The Honey Hut, Think of “ On Golden Pond", vacation rental in Winchester

The Honey Hut, Think of “ On Golden Pond"

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Dairy Dream Farm Stay ~  It's Udderly Perfect!, vacation rental in Winchester
The Dairy Dream Farm Stay ~  It's Udderly Perfect!, vacation rental in Winchester
The Dairy Dream Farm Stay ~  It's Udderly Perfect!, vacation rental in Winchester

The Dairy Dream Farm Stay ~ It's Udderly Perfect!

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Lovely Townhome in Horse Country/Lexington, Ky-Located near Keeneland and city!., vacation rental in Winchester
Lovely Townhome in Horse Country/Lexington, Ky-Located near Keeneland and city!., vacation rental in Winchester
Lovely Townhome in Horse Country/Lexington, Ky-Located near Keeneland and city!., vacation rental in Winchester

Lovely Townhome in Horse Country/Lexington, Ky-Located near Keeneland and city!.

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Spacious, beautiful and cozy house, quiet neighborhood., vacation rental in Winchester
Spacious, beautiful and cozy house, quiet neighborhood., vacation rental in Winchester
Spacious, beautiful and cozy house, quiet neighborhood., vacation rental in Winchester

Spacious, beautiful and cozy house, quiet neighborhood.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Lovely 3 Bdrm Home w/Free Parking Close to I-75!, vacation rental in Winchester
Lovely 3 Bdrm Home w/Free Parking Close to I-75!, vacation rental in Winchester
Lovely 3 Bdrm Home w/Free Parking Close to I-75!, vacation rental in Winchester

Lovely 3 Bdrm Home w/Free Parking Close to I-75!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Escape to Comfort in Lexington/Hamburg: Stylish 3BR/2.5BA Home, vacation rental in Winchester
Escape to Comfort in Lexington/Hamburg: Stylish 3BR/2.5BA Home, vacation rental in Winchester
Escape to Comfort in Lexington/Hamburg: Stylish 3BR/2.5BA Home, vacation rental in Winchester

Escape to Comfort in Lexington/Hamburg: Stylish 3BR/2.5BA Home

Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Creekside Home on Boone Creek in Lexington Ky., vacation rental in Winchester
Creekside Home on Boone Creek in Lexington Ky., vacation rental in Winchester
Creekside Home on Boone Creek in Lexington Ky., vacation rental in Winchester

Creekside Home on Boone Creek in Lexington Ky.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Kentucky River Cottages ~ Featured on the Live Well Network's Sweet Retreats!, vacation rental in Winchester
Kentucky River Cottages ~ Featured on the Live Well Network's Sweet Retreats!, vacation rental in Winchester
Kentucky River Cottages ~ Featured on the Live Well Network's Sweet Retreats!, vacation rental in Winchester

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

Rental Home
3 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Lexington Near downtown/keeneland/interstate. Pool table. Self check in 3000sqft, vacation rental in Winchester
Lexington Near downtown/keeneland/interstate. Pool table. Self check in 3000sqft, vacation rental in Winchester
Lexington Near downtown/keeneland/interstate. Pool table. Self check in 3000sqft, vacation rental in Winchester

Lexington Near downtown/keeneland/interstate. Pool table. Self check in 3000sqft

Rental Home
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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A Breath of Fresh Air... Jordan Hill Farm, vacation rental in Winchester
A Breath of Fresh Air... Jordan Hill Farm, vacation rental in Winchester
A Breath of Fresh Air... Jordan Hill Farm, vacation rental in Winchester

A Breath of Fresh Air... Jordan Hill Farm

Rental Home
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Hill 'n' Dale Kentucky Thoroughbred Horse Farm at Xalapa, vacation rental in Winchester
Hill 'n' Dale Kentucky Thoroughbred Horse Farm at Xalapa, vacation rental in Winchester
Hill 'n' Dale Kentucky Thoroughbred Horse Farm at Xalapa, vacation rental in Winchester

Hill 'n' Dale Kentucky Thoroughbred Horse Farm at Xalapa

Rental Home
3 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Modern 4 bedroom fenced in yard-Hamburg, vacation rental in Winchester
Modern 4 bedroom fenced in yard-Hamburg, vacation rental in Winchester
Modern 4 bedroom fenced in yard-Hamburg, vacation rental in Winchester

Modern 4 bedroom fenced in yard-Hamburg

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Large and Luxurious, with Green Space, vacation rental in Winchester
Large and Luxurious, with Green Space, vacation rental in Winchester
Large and Luxurious, with Green Space, vacation rental in Winchester

Large and Luxurious, with Green Space

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Welcome Hall 5 bedroom 1880’s home on 55 acres, vacation rental in Winchester
Welcome Hall 5 bedroom 1880’s home on 55 acres, vacation rental in Winchester
Welcome Hall 5 bedroom 1880’s home on 55 acres, vacation rental in Winchester

Welcome Hall 5 bedroom 1880’s home on 55 acres

Rental Home
5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Private Country Estate: 16 miles to Keeneland, 13 to KY Horse Park!, vacation rental in Winchester
Private Country Estate: 16 miles to Keeneland, 13 to KY Horse Park!, vacation rental in Winchester
Private Country Estate: 16 miles to Keeneland, 13 to KY Horse Park!, vacation rental in Winchester

Private Country Estate: 16 miles to Keeneland, 13 to KY Horse Park!

Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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1840 Historic Antibellum Estate in the heart of the Bluegrass, vacation rental in Winchester
1840 Historic Antibellum Estate in the heart of the Bluegrass, vacation rental in Winchester
1840 Historic Antibellum Estate in the heart of the Bluegrass, vacation rental in Winchester

1840 Historic Antibellum Estate in the heart of the Bluegrass

Rental Home
8 bedrooms
9 bathrooms
Sleeps 20
Match: Sleeps
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Northwoods Offgrid Cabins - Discover Living Off the Grid in the Appalachians, vacation rental in Winchester
Northwoods Offgrid Cabins - Discover Living Off the Grid in the Appalachians, vacation rental in Winchester
Northwoods Offgrid Cabins - Discover Living Off the Grid in the Appalachians, vacation rental in Winchester

Northwoods Offgrid Cabins - Discover Living Off the Grid in the Appalachians

Cabin
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Hill n Dale Thoroughbred Horse Farm at Xalapa , vacation rental in Winchester
Hill n Dale Thoroughbred Horse Farm at Xalapa , vacation rental in Winchester
Hill n Dale Thoroughbred Horse Farm at Xalapa , vacation rental in Winchester

Hill n Dale Thoroughbred Horse Farm at Xalapa

Rental Home
3 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
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Showing results 1-50 of 50
Frequently Asked Questions about Winchester