Winchester Vacation Rentals

Name: 4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
Price range: $292 total

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Vacation Rentals in Winchester

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

‘Clara’ Just Off I-75! 2 Full Bedrooms!

Lexington KY

$145 nightly

$168 total

Oct 25 - Oct 26

Total with taxes and fees

With a stay at this vacation home in Lexington, you'll be within a 10-minute drive of Lexington Convention Center and Rupp Arena.

Kitchen

Luxe Home Downtown - Sleeps 6. Off-street parking

Lexington KY

$246 nightly

$264 total

Nov 3 - Nov 4

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.

Kitchen

Washer

The Historic Fairway Estate: Downtown Lex, Ky Luxury in the Horse Capital

Lexington KY

With a stay at this vacation home in Lexington (Fairway), you'll be within a 5-minute drive of University of Kentucky and Lexington Convention Center.

Kitchen

Washer

Cecil's Cozy Cottage

Lexington KY

$220 nightly

$224 total

Oct 27 - Oct 28

Total with taxes and fees

With a stay at this vacation home in Lexington, you'll be a 5-minute drive from University of Kentucky and 6 minutes from Red Mile Racetrack.

Kitchen

Washer

Cozy 1-bedroom in Lexington

Lexington KY

$196 nightly

$228 total

Oct 25 - Oct 26

Total with taxes and fees

With a stay at this vacation home, you'll be centrally located in Lexington, steps from University of Kentucky and a short 3-minute drive from Rupp Arena.

Kitchen

Washer

Charming Cottage - Near I-75 & Horse Park + Farms

Lexington KY

$267 nightly

$310 total

Oct 21 - Oct 22

Total with taxes and fees

With a stay at this vacation home in Lexington, you'll be within a 10-minute drive of Lexington Convention Center and Rupp Arena.

Kitchen

Washer

Mins to UK- Rupp- Kroger Field- Blocks away to UK & ST Joes Hospital-

Lexington KY

$230 nightly

$267 total

Oct 21 - Oct 22

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 Red Mile Racetrack and University of Kentucky.

Kitchen

Washer

Cute bungalow located in the Fairwood neighborhood of Lexington. #15081244-1

Lexington KY

With a stay at this vacation home, you'll be centrally located in Lexington, a 5-minute drive from University of Kentucky and 5 minutes from Lexington Convention Center.

Kitchen

Washer

Hot Tub/Playground/12 min to Horse Park/30min Ark

Georgetown KY

$336 nightly

$353 total

Oct 21 - Oct 22

Total with taxes and fees

With a stay at this vacation home in Georgetown, you'll be within a 10-minute drive of Kentucky Horse Park and Georgetown College.

Hot Tub

Kitchen

Sandstone Lodge, Ride to Hollerwood + DBBB Access

Stanton KY

$433 nightly

$477 total

Nov 16 - Nov 17

Total with taxes and fees

With a stay at this vacation home in Stanton, you'll be 3.3 mi (5.2 km) from Natural Bridge State Park and 13.8 mi (22.2 km) from Red River Gorge Geological Area.

Kitchen

Washer

4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

Winchester KY

$265 nightly

$292 total

Oct 25 - Oct 26

Total with taxes and fees

Located in Winchester, this vacation home is within a 5-minute drive of College Park and Community Park.

Kitchen

Washer

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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.