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Compare 440 Vacation Homes in Winchester with updated reviews, rates, and availability.

"Beautiful property and amazing host!Communication is top notch!This was our third time staying at this homey cabin and hope to visit again in the future!"

"Will definitely be back. "

"Would definitely stay again!"

AED 787 total

includes taxes & fees

2 Jun - 3 Jun

"We are repeat customers, will definitely try to rent again. "

3 bedrooms, desk, iron/ironing board, free WiFi

"Definitely recommend staying here. Not too far from 75, and tons of places in Richmond and nearby for shopping/restaurants. Place was very clean, comfortable furniture and beds. Quiet neighborhood, just a cozy place to stay."

AED 810 total

includes taxes & fees

2 Jun - 3 Jun

"We really enjoyed our stay. Was very comfortable and welcoming home. "

AED 1,899 total

includes taxes & fees

15 Jun - 16 Jun

"The front porch is absolutely amazing! There is a good bit of traffic going by but we spent hours out there visiting and just relaxing."

"Another great stay; perfect for our Family!!"

"This house was perfect accommodations for our group of 3 couples. It was very clean and well stocked. The neighborhood is quiet. The location in Georgetown was convenient to Lexington attractions as well as to restaurants in downtown Georgetown. We recommend this VRBO highly. "

AED 1,146 total

includes taxes & fees

30 Jun - 1 Jul

"The cabin is very nice and it was in a nice quiet area, which is exactly what I was looking for. Convenient location to great hiking spots. I would gladly stay here again, it was great. "

"Great place to stay if you aren't looking to get to fancy and just need a place to lay your head down between hikes"

"We stayed here for a night and attended an event at the Greyline station for the weekend! Wish we could of stayed long ! Next time! Amazing property!"

AED 1,425 total

includes taxes & fees

3 Jun - 4 Jun

"We enjoyed it very much! Beautiful home and peaceful atmosphere!"

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

"A terrific area! Convenient to restaurants, shopping, and the New Circle exit. There's a neighborhood park behind the home and ducks have been through the yard. Neighbors are nice and it's safe for families and groups. We love it here! House was clean and well appointed. Highly Recommended!"

AED 942 total

includes taxes & fees

3 Jun - 4 Jun

"Convenient to downtown, hospitals and campus. "

"Super nice and clean "

AED 1,028 total

includes taxes & fees

25 Jun - 26 Jun

"The house is very comfortable, clean and well stocked. And the location is so convenient to the airport, Keeneland, UK, shopping and dining. And the host is great! We visit Lexington a couple times a year and this is one we’ll definitely want to stay in again. "