Vacation rentals in Winston

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Top-rated vacation rentals in Winston

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Superhost

Apartment in Roseburg

Hilltop Tourists! 2Bdrm 1Bth Full Kitchen & Views

Welcome to Beulaire, our Mid Century Retreat overlooking Roseburg in the Beautiful Umpqua Valley. Our Suite is a 2 bedroom Guest Suite with its own private entrance, full kitchen and stunning views!! April and Paul, reside in the separate upstairs level while you enjoy your exclusive stay! Walk to Charming Downtown Roseburg discovering Dining, Breweries, Shopping & Salons. A short drive to the Beautiful Vinyard Loop & Crater Lake just 90 minutes away, down hwy 138...the hwy of waterfalls!

$107 per night

Superhost

Cottage in Roseburg

Bella's Cozy Cottage, Entire home with yard use

Yay! We just installed permanent air/heating system.This sweet little 40's cottage was completely renovated inside & is full of charm & period pieces.Just 1/4 mile off I-5 in a nice, quiet neighborhood. Very close to VA, bike path, shopping CTR, grocery stores ( Fred Meyers,Grocery Outlet), coffee, restaurants & fast foods. Close to Mercy Hos. Great location for day trips to the Oregon Coast, Crater/Diamond Lakes, fishing, boating, Umpqua Valley Wines, Golfing, WildLife Safari & more!

$83 per night

Superhost

Guest suite in Roseburg

Umpqua Valley Garden Getaway

Minutes from several award-winning wineries and local fishing holes, the Umpqua Valley Garden Getaway has all the amenities you will need for a memorable vacation. Down a cobblestone stairway, you will find a pristinely redesigned cottage nestled in a private backyard garden. Start your day with a hot cup of coffee from the wicker chairs overlooking the backyard and end your day dining al fresco as string lights dangle above a cozy corner of the deck.

$79 per night