Search Vacation Homes in Winchester

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Vacation Homes in Winchester

Stroll up to the charming front entrance, flanked by two windows with shutters, and enter through the green door.

"We had a great time staying here. Barely noticed the highway noise. "

$228 nightly

Aug 7 - Aug 8

Total includes taxes and fees

Houses with gabled and flat roofs line the quiet neighborhood, surrounded by trees and a fence.

"My week stay was great! Hosts were flexible and accommodated a reservation change to add two additional days. Would highly recommend for anyone staying in Lexington!"

$216 nightly

Aug 7 - Aug 8

Total includes taxes and fees

Enjoy cooking in this well-equipped kitchen with a large window, stainless steel appliances, and a dishwasher.

"We had a great stay. Perfect for multigenerational families."

$418 nightly

Sep 2 - Sep 3

Total includes taxes and fees

Stunning two-story home with a symmetrical facade, featuring a combination of siding and stone accents.

"We had a great stay for a wedding weekend in Lexington. Centrally located, clean and comfortable. The owners were great communicators and the house was perfect."

$666 nightly

Aug 17 - Aug 18

Total includes taxes and fees

Enjoy cooking in this well-lit kitchen with a central island, oven, and ample counter space.

"Perfect location for us to enjoy with friends who have never been to Lexington before! Keeneland, bourbon trail and our accommodations did not disappoint! The whole process was seamless thanks to our amazing host! "

Enjoy meals in the kitchen with stainless steel appliances and a central island, adjacent to a dining area with a wooden table and comfortable seating.

"The townhouse was very clean and organized. Jennifer provided all of the basic supplies needed and her communication was excellent!"

Enjoy cooking in this well-equipped kitchen with a microwave, oven, refrigerator, and dishwasher.

"This is a great property! We were so close to the things we wanted to see and do. Was such a nice house and would definitely stay again!!"

Enjoy cooking in this well-equipped kitchen with a gas stove, oven, and refrigerator, complemented by a dining area with a table and chairs.

"Overall good stay. Plenty of room for families."

$663 nightly

Aug 11 - Aug 12

Total includes taxes and fees

Stunning two-story house with a central entrance, flanked by windows and a door, set amidst beautifully maintained lawns and lush trees.

"Nicely upgraded unit, relaxing and comfortable. Close to everything!"

$209 nightly

Aug 13 - Aug 14

Total includes taxes and fees

Enjoy a peaceful outdoor space with a table and chairs on the deck, surrounded by a fence.

"Enjoyed our stay. Location was great. "

$276 nightly

Aug 10 - Aug 11

Total includes taxes and fees

Relax in a hot tub surrounded by a forested area.

"Loved our stay here, we had everything we could possibly need!"

$276 nightly

Aug 17 - Aug 18

Total includes taxes and fees

Relax in a spacious living area with a sofa set and flat-screen TV, and cook in a well-equipped kitchen with microwave, oven, and refrigerator.

"It was very nice and clean and very comfortable! "

$343 nightly

Sep 1 - Sep 2

Total includes taxes and fees

Modern kitchen with a microwave, dishwasher, stove, and sink, featuring pendant lights and a window with blinds.

"Super location, amenities, very clean, fenced yard for our dog was a definite bonus. Would rent again for sure!"

$222 nightly

Aug 7 - Aug 8

Total includes taxes and fees

Enjoy cooking in this well-equipped kitchen with an oven, microwave, and coffee maker.

"Perfect spot plent of beds, great neighborhood near everything!"

Relax in the serene outdoor patio with a hot tub under a shaded pergola.

"Great location to walk to shopping/dining and easy drive to the horse park. It was a great stay!"

$373 nightly

Sep 2 - Sep 3

Total includes taxes and fees

Enjoy cooking in this well-equipped kitchen with a stainless steel range, mosaic tile backsplash, and ample cabinetry.

"Great stay. Great place."

Enjoy cooking in this kitchen with a sleek dishwasher, oven, and microwave, plus ample counter space.

"We came for the K3DE at the horse park and this property was the perfect distance between the horse park and some nice restaurants in the city. We all really like the house it was a nice size and very cute. "