Holiday Homes in Winchester

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Featured Holiday Homes in Winchester

"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!"

includes taxes & fees

28 Aug - 29 Aug

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

"We gambled n we won"

includes taxes & fees

28 Aug - 29 Aug

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

includes taxes & fees

31 Aug - 1 Sept

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

includes taxes & fees

22 Sept - 23 Sept

"Property was spacious, clean, and inviting. Host was very fast to reply and helpful. Plently of room for kids to spread out. Pool was large and hit all around. Easy to find and within trip to stores if you forgot anything. Very well furnished, even had pool toys and some life jackets. Can't wait to stay again. Easily became one our top rentals we have stayed at. "

"Just a few days in Lexington "

includes taxes & fees

1 Sept - 2 Sept

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

includes taxes & fees

28 Aug - 29 Aug

"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!"

includes taxes & fees

28 Aug - 29 Aug

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

includes taxes & fees

1 Sept - 2 Sept

"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 "

includes taxes & fees

9 Sept - 10 Sept

"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😁"

includes taxes & fees

1 Sept - 2 Sept

"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!"