Search Holiday Homes in Winchester

"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...

"The house was so nice! Functional and beautiful kitchen, large dining room table for 8, beds were more comfortable than mine at home- we all slept really sound. 2 full baths. Huge backyard- they had the fire built and ready in the firepit! Within walking distance to charming downtown Georgetown. Host was responsive. A perfect place. We hope to return"

"Great location, clean house"

"We decided to stay in Lexington due to things we planned to do before going to the Oaks and Derby. The house is very clean and just like the pictures. It’s close to stores and restaurants but still in a quiet neighborhood. Loved that every bedroom had its own bathroom. Also appreciated the use of the garage. Would recommend staying here."

"Listing resembled pics from site. Accurate timings to local destinations. Messaged about an item left behind after check out and no response given from the owner. Not ideal."

"Couldn’t have been happier with our stay and every aspect! The neighborhood was very nice and so close to MANY restaurants, grocery stores, and the highway. The house was so cozy! Absolutely beautiful home! Beds so comfy, I ordered that brand comforter on my way home ☺️ The owners had a sweet welcome basket for us and made the process so easy! Can’t wait to visit again!"

"Such an adorable house. We were looking for a rental that had history not something newer. This bungalow surprised us. Oozes charm! Close to everything. Backyard is very large, house is clean and beds were comfortable. We had such an enjoyable time watching people go by and chatting with neighbors on the front porch. Thank you for sharing this gem!"

"Lovely home in a quiet town outside of Lexington. Would love to return again next year."

"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."

"Loved location and hot tub"

"This place was more then I expected! The host, Carlos was awesome. Any time I had a question he was right there with a response. Talk about amenities, I ran out 1 time in 4 days. Door dash worked great to get food when we werent cooking what we brought. My intention was to let my husband relax in a hot tub for birthday and eat good food undisturbed and thats exactly what we got. We brought our 2 dogs and the fenced in yard was perfect. Highly recommend staying here!"

"This was perfect for our UK moms weekend getaway. Check in and communication was very easy & prompt responses from Seth. Comfortably slept 6 (if you shared beds could even be more). Great/ safe location, easy to Uber or Lyft to Campus. Would definitely stay again when in town with a group for a UK event!!"

"The home was beautiful and in a quiet and safe neighborhood. Highly recommend this listing!"

"Property was adorable, clean and comfy."

"The house and farm are beautiful! Everything is neat and clean; and beautifully decorated. Beds are very comfortable. And Julia is the absolute best host! Great communication; Fully stocked refrigerator and pantry, including homemade chocolate chip cookies and so many other “extras”!! Even helped arrange a last minute awesome tour at a local stallion farm on Derby weekend. The best VRBO stay ever!"

"We came down from Michigan for the Defender 3 Day Event at the KHP! The home was in the perfect location for all of our needs and was just a short drive to the park! The home was ultra clean, well equipped and the beds were oh so comfy! The hosts attention to detail was much appreciated!"

"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 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."

"Nice home, very comfortable and clean. Easy check in and good communications with the host. 5 Stars"

"Great place to stay for UK graduation, distilleries or the Derby. Lots of space and parking. Clean and easy access - good communication."

"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!"

"First off, we would go out of our way to stay here again. The property was beautiful and the pictures of the cabin do not do it justice. The property owner was very easy to communicate with and responded quickly when you send a message. The cabin and property were immaculately clean and ammenities were very well kept.This has been added as a must stay next time we are in the area."

"Great little cabin in the woods. Pretty much as advertised. The beds were not good. Very mushy and soft. My chiropractor will have fun with me at our next appointment."