Winchester Vacation Rentals

Name: Summer Special 🥃 Bourbon Trail-Downtown-Mins to Rupp-UK-Restaurant-Renovated 🐎
Price range: $318 total

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Vacation Rentals in Winchester

Cozy 1-bedroom ranch house in Georgetown on 10 acres with horse paddock.

Georgetown KY

$171 nightly

$188 total

Sep 1 - Sep 2

Total with taxes and fees

Located in Georgetown, this vacation home is in a rural location, within a 5-minute drive of Country Boy Brewing and Toyota Visitor Center.

Kitchen

Washer

Bhie Lovely Hideaway | RRG | Peaceful | Cozy Stay. Stanton location, just steps from Kroger and a short 15-minute drive to Natural Bridge. Ideal home base for hikers + climbers, featuring a modern kitchen, firepit, grill, covered patio

Stanton KY

Located in Stanton, this vacation home is in a rural location, within a 15-minute drive of Kentucky Reptile Zoo and Osborne Bend Trail.

Kitchen

Washer

Great Locatoin- Mins to Rupp-Kroger Field-Downtown Lexington- Modern Retro 70's

Lexington KY

$268 nightly

$311 total

Aug 26 - Aug 27

Total with taxes and fees

With a stay at this vacation home in Lexington, you'll be within a 5-minute drive of University of Kentucky and Red Mile Racetrack.

Washer

Dryer

Town home with private garage

Lexington KY

With a stay at this vacation home, you'll be centrally located in Lexington, within a 5-minute drive of University of Kentucky and Rupp Arena.

Kitchen

Washer

Luxe Home Downtown - Sleeps 6. Off-street parking

Lexington KY

$239 nightly

$255 total

Aug 27 - Aug 28

Total with taxes and fees

With a stay at this vacation home, you'll be centrally located in Lexington, within a 5-minute drive of Rupp Arena and University of Kentucky.

This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.

Lexington KY

$184 nightly

$187 total

Aug 31 - Sep 1

Total with taxes and fees

With a stay at this vacation home in Lexington, you'll be within a 15-minute walk of Red Mile Racetrack and University of Kentucky.

Kitchen

Washer

Keeneland/Airport/Downtown Tulsa Time!

Lexington KY

With a stay at this vacation home in Lexington, you'll be within a 5-minute drive of University of Kentucky and Red Mile Racetrack.

Kitchen

Washer

DOWNTOWN, Rupp Arena just 5 min away. 2 bedr/1 Bath cozy home.

Lexington KY

With a stay at this vacation home in Lexington (Northside District), you'll be within a 5-minute drive of Rupp Arena and University of Kentucky.

Kitchen

Washer

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

Lexington KY

With a stay at this vacation home in Lexington, you'll be within a 15-minute drive of University of Kentucky and Rupp Arena.

Cozy Farmhouse • Downtown • Wi-Fi • Quiet Setting• 10 Minutes to RRG

Stanton KY

$233 nightly

$264 total

Aug 30 - Aug 31

Total with taxes and fees

Located in Stanton, this vacation home is in a rural location, within a 15-minute drive of Kentucky Reptile Zoo and Osborne Bend Trail.

Downtown Townhouse Near Rupp Arena

Lexington KY

Located in Lexington (Downtown Lexington), this vacation home is within a 15-minute walk of Rupp Arena and University of Kentucky.

Kitchen

Washer

Summer Special 🥃 Bourbon Trail-Downtown-Mins to Rupp-UK-Restaurant-Renovated 🐎

Lexington KY

$274 nightly

$318 total

Aug 26 - Aug 27

Total with taxes and fees

With a stay at this vacation home, you'll be centrally located in Lexington, within a 5-minute drive of University of Kentucky and Rupp Arena.

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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.