Search Vacation Homes in Winchester

Change your mind

Book hotels with free cancellation

Treat yourself

Be picky

Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Vacation Homes in Winchester

Our top choices for Winchester vacation homes

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

"House was cute and great location in downtown Lexington! "

SAR 800 total

includes taxes & fees

29 Sep - 30 Sep

Fridge, coffee/tea maker, cookware/dishes/utensils

"We gambled n we won"

SAR 1,007 total

includes taxes & fees

4 Sep - 5 Sep

"This property is cute and worked well for our needs. Great communication. Clean. Would definitely consider staying again if in the area."

SAR 911 total

includes taxes & fees

2 Sep - 3 Sep

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

SAR 819 total

includes taxes & fees

22 Sep - 23 Sep

"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 "

SAR 702 total

includes taxes & fees

2 Sep - 3 Sep

"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!"

SAR 1,363 total

includes taxes & fees

10 Sep - 11 Sep

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

SAR 1,797 total

includes taxes & fees

2 Sep - 3 Sep

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

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

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😁"

SAR 1,254 total

includes taxes & fees

2 Sep - 3 Sep

"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 "

SAR 869 total

includes taxes & fees

30 Sep - 1 Oct

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

"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!"