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Vacation Homes in Winchester

Our top choices for Winchester vacation homes

"Very nice property. "

"Wonderful hosts. "

Fridge, oven, stovetop, coffee/tea maker

"Renee was an absolute delight to communicate with and I’m appreciative of her hospitality. This place is absolutely adorable and secluded. It was a nice and peaceful New Year’s Eve. "

"It was such a nice little spot to get away."

"Extremely clean home in a safe neighborhood! We had everything we needed! Host was very kind and communicative! Would love to stay there again! "

SAR 1,187 total

includes taxes & fees

22 Sep - 23 Sep

"We have stayed at this property now multiple times and it has been clean, easy, great location, everything works and we will definitely be back"

SAR 814 total

includes taxes & fees

19 Sep - 20 Sep

"Bill's house was comfortable, and the house and property were consistent with the listing. The house and furnishings worked well for my family for our one-night stay."

"Enjoyed the accommodations. just as advertised would stay again."

SAR 653 total

includes taxes & fees

9 Sep - 10 Sep

"Just the right size and location for a wine country getaway weekend. Had everything we needed, and more. Will not hesitate to book again next trip, if it's available."

"I grew up in the area but had never had an opportunity to stay here before. Joanne was supper helpful and kind, obviously loves this lodge. Our room (#1) was spacious, and there were food offerings (in addition to our welcome gift of zucchini bread) across the street, and a few places nearby. Although close to the street, we found the rustic appeal of this lodge overwhelmed the noise of the traffic, that depending on where you stay in the lodge you might not hear at all. Will stay here again...

"We stayed here for a night since we had a nearby disc golf tournament. Leah was a great host and the house was super clean and comfy. Quiet neighborhood, cool back porch to hang out. Highly recommend! Thank you Leah!"

SAR 1,464 total

includes taxes & fees

9 Sep - 10 Sep

"April answered all my emails immediately and was very nice. Loved the location."

SAR 809 total

includes taxes & fees

10 Sep - 11 Sep

"Excellent experience! We were passing through and wanted a cozy experience from multiple hotel stays. Our hosts were outstanding and so friendly, attentive to every little detail to make us feel welcomed and comfortable. An outstanding bed and breakfast experience!"