Holiday Homes in Winchester

"Set atop a hill behind the winery, this well-appointed cottage had everything we needed for a restful stay. The property is located off the beaten path and only about a 4-minute drive to the roundabout. The kitchen was well-stocked, and the linens and towels are exquisite! The hosts even left fresh cream in the fridge for our coffee. The bed was super comfortable, and there is plenty of space inside the room so we didn't feel cramped. I think they're still working on the guest property, so for...

"Chris was an amazing host! We had no small children so our stay was perfect and amazing! Comfortable beds and very spacious home!!! I’m a local resident and this home absolute perfect for my family and friends! Amazing time! We will be a rerun guest for sure!!"

"Grandeur! Beautiful views and beautiful place to stay with family! Thanks Rochelle💕"

"Overall All of us had a great time The place was immaculate!! Great location , really close to town, Mrs. Dirk was fast to answer our call when we had a question, we really enjoyed the stay, for our next getaway and if we have something planned close by We’d love to stay there again Thank you so very much!!"

"This was an amazing place for our girls trip and wine tasting. Owner was amazing and let us drop off our stuff early so it did not sit in our hot cars while we were out wine tasting. The property is so cute, and comfortable, bedrooms and living areas were clean, backyard was amazing."

"One of the best places we have ever stayed at! The house is spacious especially the Master Suite. Go outside and pick fresh lemons, oranges, guavas and even artichokes. The property is so big it has hiking trails. The best part are the owners Amy and Frank. They are very nice people and super accommodating! We will definitely be back to the area and we would go out of our way to stay here again!"