Search Holiday Homes in Winchester

"I stayed in Lexington for a week for my son’s surgery. This house had everything I needed. A nice back yard for my dog to romp and play. Close proximity to food and medical center Will definitely be back"

"This historic home is in the best neighborhood in Lexington, right in the middle of other historic homes and walking distance to many great restaurants. It is nicely appointed, very clean, and very comfortable. The listing photos depict it very well. My family and I would stay here again."

"This house is always clean and welcoming on arrival. The location is great with lots of restaurants and shopping nearby. We golfed every day of our stay and the area courses are in great shape and reasonably priced. We love it here and hope to return."

"The location was perfect for the Kentucky theater, and there were nice dining options in walking distance. The home was easy to access, and the cookies were AMAZING. The biggest drawback was that we couldn’t get the wi fi to work (although the antenna did mostly). "

"First and for most the cleaning fee was 100% reasonable, and then the host didn’t expect me to clean the house before leaving. This. Is.Huge! And made check out so simple!!!! They had lots of the necessities that you often have to buy such as dishwashing soap, even laundry detergent, lots of TP etc…so no need to make a trip to the store for that such an extra bonus! Host was so communicative and great help! Super Clean house as well! Only two negatives were there was no iron and this is a...

"This house is perfect no matter what your plans. Centrally located, it’s close to UK, short drive to Keenland or Rupp Arena. The neighborhood is quiet, the backyard was fenced which was a bonus, as my big lab travels with me. I slept like a rock, so I give A+ for the mattress. Allen was a wonderful host, answering e mails promptly. When in Lexington, I’ll always check for availability here. Highly recommend."

"This house was amazing! It was beautifully furnished and had plenty of room. It was entirely updated, clean and the owners thought of everything. The amenities were exceptional. I highly recommend this VRBO!!"

"Great location! We went to horse races at Keeneland on Saturday (about 40 minute drive) and hiked East Pinnacle in Berea College Forest on Sunday (about 20 minute drive). Beautiful and so much fun! House was spotless and included all necessary amenities. Host was very responsive to all my questions; provided lots of tips on dining options in area. EKU is just a block away! Beautiful campus to take a walk."

"Perfect for the 6 of us. We enjoyed the outdoor space and gaming."

"This is my groups second stay at this property and it didn’t disappoint. Well adorned, comfortable furnishings and a great location. We will absolutely be back."

"We enjoyed our stay at this quaint house. It was immaculate, well appointed, and welcoming."

"We read the amazing reviews and somehow this bungalow was even better than expected. The place was super clean and way bigger than it looked in the photos. It's in an awesome spot, really close to tons of restaurants and the UK campus, but still super quiet. We enjoyed sitting on the front porch, riding the bikes over to the UK campus, and relaxing in 5hr comfy beds with lots of pillows. Perfect for anyone wanting a mix of convenience and peace. Highly recommend!"

"Very nice place to stay and town was very quiet. We all enjoyed our stay."

"Property was adorable, clean and comfy."

"Spacious, attractive home; well stocked kitchen; good location adjacent to attractive, walkable neighborhood. Each bedroom had its own bathroom. Couldn’t have worked better for 5 couples."

"Great space for a relaxing weekend in Lexington. We had 5 couples come to visit our UK student and spend the day at Keeneland The house is a perfect layout for hanging with friends. Only surprise was the 5th bedroom was a walk through with 2 queen beds"

"Such a unique place right on the horse farm. Loved it."

"We’ll stocked and comfortable"

"The size of the house makes it more convenient for multiple people to stay over a hotel. The guest bathroom is a tad awkward with the shower door and being blasted with cold water (faucet is on far wall) but the house was well stocked and overall comfortable."

"The owner did an excellent job in running this cute house into a short term rental. They do a better job than most of us with what they have in space and neighborhood."

"Very nice place!"

"The cabin was amazing. Nice and peaceful location. The cabin had everything that we needed. The jacuzzi was nice and relaxing, My wife enjoyed it very much! We are planning to get one at home shortly. The location of the property was a little puzzling at first. When we started to venture of and visit locations. The placement of the property made perfect sense! You’re literally right in the middle of everything that you will want to see! Everything interesting is just a few miles away! My wife...

"We loved how secluded it was, but close to the park and restaurants. The hot tub and fire pit were a nice addition. It was well decorated and felt upscale. I liked that it had k-cups. Love the travel pics on the wall. We had a great time and enjoyed the accommodations. Overall a wonderful get away. We will definitely be back!"