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Compare 424 Vacation Homes in Winchester with updated reviews, rates, and availability.

"We were in town for a sporting event on campus and discovered the apartment was very conveniently located...not only to the University of Kentucky campus but to other popular sites in town. The apartment included a very modern kitchen and a very nice Kroger grocery within easy walking distance with which to stock that kitchen. We missed a more defined living room area, but the comfy king size bed, large shower, and off street parking made up for it. We would definitely stay here again."

AED 837 total

includes taxes & fees

25 Mar - 26 Mar

"We had a great stay. House was beautiful and location was awesome. "

AED 1,935 total

includes taxes & fees

23 Mar - 24 Mar

"The house was extremely welcoming. Our bed was great after a LONG drive to KY. It has everything we needed to enjoy time with our daughter n her boyfriend. (who just moved to Lexington) The location was near everything we needed to be at and the host was excellent in his response time with questions or suggestions. Will definitely look at staying again when we come to town. "

AED 818 total

includes taxes & fees

26 Mar - 27 Mar

"The location is convenient yet private. Decorated very well and the house had everything we needed for the weekend. The beds were great! Love the back yard. And the host was pleasant, helpful, and quick to respond! "

"The place served our purposes very well. It was very nice and clean. The owners were very helpful and accommodating. We need to stay at this place in the summer so we can enjoy the enclosed porch. "

"Everything went very smoothly for our stay - easy self check-in and checkout. House was clean and well main and it was great being able to use the garage."

"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 725 total

includes taxes & fees

1 Apr - 2 Apr

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

"Clean and pretty good for the price "

AED 969 total

includes taxes & fees

23 Mar - 24 Mar

"The home was clean with full size beds in each room and two bathrooms. The home is close to a lot of neat places to visit and eateries. It was exactly what we expected and wanted. Thank you!"

AED 1,209 total

includes taxes & fees

24 Mar - 25 Mar

"Place was amazing, clean and perfect location for our adventures in bourbon country."

AED 1,255 total

includes taxes & fees

23 Mar - 24 Mar

"Great job on the remodel! Awesome place, has everything you need and it is exactly as described! Great place for your dog! Walking distance to downtown to restaurants! Definitely would stay there again! Also host was awesome!"

AED 1,594 total

includes taxes & fees

16 Apr - 17 Apr

"It worked great for us "

"This place was spotless, and it is the second time I stayed. The location works well for me. But it is a 10 minute drive into the center of Lexington. It is a very comfortable place and not overly decorated so there is no clutter to contend with. Appliances are new. Just wish there was a regular drip coffee pot instead of Keurig. The living room tv is tough to connect too and I ended up using HDMI cords. I couldn't Airplay or chrome cast with either my lap top or iPad. Internet is fast...

"Very conveniently located to downtown. Very clean, highly recommend."

AED 753 total

includes taxes & fees

1 Apr - 2 Apr

"We needed a place equal distance for our family to celebrate an early Christmas. We were very pleased with the property. It was clean and had enough room for all our activities. We had a great time."

"A quaint place. Must love horses! lol. Had everything that we needed for our short stay and communication was speedy for any questions or issues we had. Will be staying again."

AED 700 total

includes taxes & fees

24 Mar - 25 Mar

"My large family of four children thoroughly enjoyed staying at the property. There was plenty to do with the hot tub and game room while simultaneously not being on top of each other due to the large rooms with attached bathrooms. Location was very close to Lexington downtown and it was easy for us to get to the south side to see family.One suggestion would be to upgrade to a tankless as the temptation to take longer showers and baths was high in the nicely designed bathrooms!"

"This was our second time staying at this cute perfect house. There were 3 couples and a few small pups. Every couple had a nice spacious bedroom and private bathroom. The kitchen was well equipped with everything you might need. Lots of seating and comfort. The house was beautifully decorated for Christmas. Highly recommended. "

AED 1,389 total

includes taxes & fees

23 Mar - 24 Mar

"Great property. Super clean. Convenient to area attractions "

AED 1,045 total

includes taxes & fees

15 Apr - 16 Apr

"This place was extremely nice and worked perfectly for our family in town for a funeral. It was a great gathering place. We will go back if the need arises. "