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Compare 9 Cottages in Winchester with updated reviews, rates, and availability.

"Cute little place! Especially liked the patio and outside areas. Inside needs a few finishing touches like coat hooks on back of doors, but place is very new, clean and worked great for our few days there."

Roseburg Vacation Rental | 1BR | 1BA | 850 Sq Ft | 1 Step Required

"This small cottage is a true charmer. Spotless, beautiful, comfortable, interesting, and in a quiet nature- filled location. Perfect for a stopover on your way to visit relatives. Couldn't have asked for more."

SAR 638 total

includes taxes & fees

26 Feb - 27 Feb

"Attractive tiny house, well equipped, peaceful neighborhood, convenient to town. Bedroom is a bit small, but living area and bath (with shower and washer/dryer) are good sized. Helpful owner suggested Brix local restaurant we really liked too. Nearby Upper Umpquah waterfalls, hiking, river rafting made a nice vacation."

"This house was beautiful, affordable, and very spacious! It had every single amenity you would need and many extras too! The host was extremely attentive and informative with check on and out process and also making sure we could contact her at any time if needed. I definitely recommend this house and will stay here again when in the area."

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Other property types in Winchester

"Beautifully decorated house! Loved the view of the river in the backyard. So clean and new! No complaints!!"

"We are repeat renters and thoroughly enjoy our home away from home every year. Thank you!"

Winston Vacation Rental | 4BR | 2BA | Stairs Required | 1,704 Sq Ft

"Rooms are spacious and each have their own controller for heat or air conditioning so you can keep the room temp to your liking. The deck is huge and perfect for hanging outside even in wet weather because it’s totally covered. Nice fully stocked kitchen with a variety of appliances and kitchen utensils. The nice surprise was the garage with the ping pong table and work out equipment. They also provide a stroller high chair and pak n play if you have a baby"