Winchester Vacation Rentals

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Browse Select Winchester Vacation Homes

Our top choices for Winchester vacation homes

"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!"

CA $299 total

includes taxes & fees

Aug 25 - Aug 26

"House was as described and worked out great for our group. "

"Everything was exquisite!!! Clean, Inviting and cozy!!!"

CA $369 total

includes taxes & fees

Aug 24 - Aug 25

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

CA $348 total

includes taxes & fees

Aug 31 - Sep 1

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

CA $311 total

includes taxes & fees

Aug 24 - Aug 25

"We had a really relaxing stay with our dogs! They really enjoyed the yard & we enjoyed the pool! We will be back again! Thank you again!"

"Just a few days in Lexington "

CA $261 total

includes taxes & fees

Aug 24 - Aug 25

"A lovely combination of historical charm with all the modern conveniences you need. And you can’t beat the location! Loved our stay."

CA $659 total

includes taxes & fees

Aug 24 - Aug 25

"Had fabulous stay. Neat, clean, plenty of room, and well taken care of. Would absolutely stay here again! "

"We absolutely loved our stay! The property was super nice and very spacious, it was in a perfect location to reach anywhere in downtown Lex. Will definitely book again!"

CA $474 total

includes taxes & fees

Aug 24 - Aug 25

"We truly enjoyed our stay here. The large kitchen is impressive. The hot tub worked well and the outdoor space was delightful."

CA $572 total

includes taxes & fees

Aug 24 - Aug 25

"We were in Lexington for my daughter’s graduation from UK and this home was clean and comfortable. There were lots of little things provided (lots of comfy blankets, snacks, etc). The location was great for us because we wanted to be close to downtown but not too close. It was very relaxing and peaceful!"

"Had a great time "

CA $309 total

includes taxes & fees

Sep 2 - Sep 3

"Walking distance to Rupp!! It was great!"

3 bedrooms, iron/ironing board, WiFi, bed sheets

"My overall stay was very relaxing and stress free .The house was very clean & beautiful inside & out. I would recommend staying at the property to anyone who is ever in town. Great communication with the host😁"

"We came into town for a work event in Lexington and Wayne was an outstanding host. Beautiful home with plenty of bedrooms to sleep a big group. Wayne was very accommodating and checked in with us throughout the stay. They made sure to provide extra towels/linens/garbage bags knowing we had a large group! I would absolutely recommend this home if you are looking in this area!"