Winston Holiday House Rentals : Search Holiday Homes

A serene lake with a reflection of a forested mountain and a small house on the shore.

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Our top choices for Winston holiday homes

The Watusi Place - A Modern Umpqua Valley Getaway

Winston

Pamela M.

includes taxes & fees

30 July - 31 July

Luxury, Full Service Bed and Breakfast - you are the only guest in our home!

Roseburg

karen m.

includes taxes & fees

18 July - 19 July

Orchard House, Orchard House Retreat

Douglas County

Gin H.

includes taxes & fees

3 Aug - 4 Aug

<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

Roseburg

Michelle C.

includes taxes & fees

22 July - 23 July

The Urban Boho Charmer with Private Backyard, BBQ & Hammock

Roseburg

Gordon

includes taxes & fees

19 July - 20 July

Blissful Solitude Cottage

Douglas County

Loyd H.

includes taxes & fees

5 Aug - 6 Aug

Home Sweet Home

Sutherlin

Barbara S.

includes taxes & fees

20 July - 21 July

Tiny House nestled into the Forest on 160 acre Playground.

Roseburg

Lee and Kristy D.

includes taxes & fees

4 Aug - 5 Aug

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Top Winston Hotel Reviews

Wolf Creek Inn & Tavern

10/10 Excellent

"The property is unique, quite old but in terrific shape and in a very quiet, peaceful area."

Quality Inn Central Roseburg

10/10 Excellent

"This is one of my favorite overnight stayover spots on I-5 as I drive this route once a Moths between Sonoma Voubty, CA and Vancouver, BC, Canada. It’s always clean and well maintained with a terrific staff. And (big issue for me)…A great complimentary breakfast with MANY protein choices. One well-meaning note to the manager: please provide a box of Facial tissues in the room, like you used to do. I get tired of removing the bathroom role off the dispenser just to wipe the sniffles 😜. I’ve stayed at the Quality Inn, Central Roseburg perhaps 8-10 times In the past year, and will be there again in two weeks. And several more times this summer. You can’t go wrong, just bring your own Kleenex. 😇"

Family-Friendly Winston Vacation Rental w/ Deck!

10/10 Excellent

"This home was perfect for our family vacation! Well stocked with everything you could need and more. The kids loved the toys and books that were already at the house. The coffee bar is AMAZING. Hands down my favorite part as well as the beautiful deck we got to hang out on. Communication with the host was easy and fast! Highly recommend this property if you’re in the area!"

Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen

10/10 Excellent

"The house was lovely and spacious, making it perfect for our visit to Winston for a wedding. It comfortably accommodated two families. The kitchen was not only spacious but also beautifully designed. We found the beds to be comfortable, and the living room furniture was equally inviting. We appreciated having access to the washer and dryer, along with the laundry soap that was provided. The little extras, like coffee supplies and shampoo, were also greatly appreciated. The property is very well-maintained, although we noticed some cobwebs and tiny spiders in several rooms, which we understand is normal for this time of year, given the wooded areas behind the home.It was a delight to see the cacti in front of the house in bloom, as we don’t often get to see that living in Northwest Oregon. We would gladly book this home again if we need to."

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Winston Holiday Homes information

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Check prices for these dates

Our top choices for Winston holiday homes

The Watusi Place - A Modern Umpqua Valley Getaway