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 vacation homes

1. The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway
Winston
10.0 out of 10, Exceptional, (60 reviews)
"Great place for us and the kids after a long day at the wildlife safari!"
United States
Jessica M.
The price is ¥25,513
¥57,928 total
includes taxes & fees
Nov 8 - Nov 9
The Watusi Place - A Modern Umpqua Valley Getaway

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

Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Roseburg
10.0 out of 10, Exceptional, (28 reviews)
"Our hosts, James and Gail, are so lovely. They really care about their guests experience and I felt they truly cared about our experience. It’s a gorgeous home that they have decorated meticulously, and made so comfortable for guests to enjoy. The bed was super comfy and the room cozy. The bedding and towels were soft and top notch. They didn’t skimp on anything. Gail is a great cook and provided homemade food, snacks, and drinks. Some items came from her garden. James is a master with sound and...
United States
Susan
The price is ¥28,821
¥34,319 total
includes taxes & fees
Nov 10 - Nov 11
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!

3. Downtown Stay at the Red Tiny Twin!

Downtown Stay at the Red Tiny Twin!
Roseburg
9.8 out of 10, Exceptional, (31 reviews)
"Close to downtown, well appointed, clean and comfortable. Thanks for a lovely stay!"
United States
Sue S.
The price is ¥12,837
¥24,817 total
includes taxes & fees
Nov 8 - Nov 9
Downtown Stay at the Red Tiny Twin!

4. The Urban Boho Charmer with Private Backyard, BBQ & Hammock

The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Roseburg
9.6 out of 10, Exceptional, (45 reviews)
"Nice place, great location."
United States
Gordon
The price is ¥19,810
¥34,709 total
includes taxes & fees
Nov 13 - Nov 14
The Urban Boho Charmer with Private Backyard, BBQ & Hammock

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

<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Roseburg
9.8 out of 10, Exceptional, (120 reviews)
"Great stay, very clean. Would stay here again."
United States
Cindan G.
The price is ¥19,018
¥31,758 total
includes taxes & fees
Nov 8 - Nov 9
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

6. Downtown Stay at the Blue Tiny Twin

Downtown Stay at the Blue Tiny Twin
Roseburg
9.6 out of 10, Exceptional, (22 reviews)
"Everything you need is in this small but efficiently planned house. The very small countertop dishwasher is so cute! Perfect place for solo or couple to stay."
United States
Beth B.
The price is ¥14,174
¥26,213 total
includes taxes & fees
Dec 1 - Dec 2
Downtown Stay at the Blue Tiny Twin

7. Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~

Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Roseburg
9.6 out of 10, Exceptional, (33 reviews)
"Finding the entry to the property was hardest part. Parking was OK. The views and the space was great. Nice central location for many places to visit."
United States
Nicole B.
The price is ¥17,324
¥29,835 total
includes taxes & fees
Nov 21 - Nov 22
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~

8. Tiny House nestled into the Forest on 160 acre Playground.

Tiny House nestled into the Forest on 160 acre Playground.
Roseburg
9.8 out of 10, Exceptional, (21 reviews)
"My friend and I had an amazing stay. We went for a walk, had dinner out on the deck and finished the night drinking wine in the double swing. The stars were amazing. Listen to the owls as we went to sleep. Great place for a get away from the city lights :)"
United States
kimberley
The price is ¥14,741
¥18,478 total
includes taxes & fees
Nov 9 - Nov 10
Tiny House nestled into the Forest on 160 acre Playground.

9. Private Ranch House, Highland Cattle, Horses & Peaceful Views - a soul refresher

Private Ranch House, Highland Cattle, Horses & Peaceful Views - a soul refresher
Myrtle Creek
10.0 out of 10, Exceptional, (3 reviews)
"The Ranch was everything you could ever want and more it was the most quiet and peaceful night my wife was over the moon with the cows there definitely will be more stays in the future"
United States
Unspecified U.
The price is ¥26,773
¥33,570 total
includes taxes & fees
Nov 8 - Nov 9
Private Ranch House, Highland Cattle, Horses & Peaceful Views - a soul refresher

10. Home Sweet Home

Home Sweet Home
Sutherlin
8.8 out of 10, Excellent, (13 reviews)
"This location worked great for our visit with family in the area. The house was clean and the beds were comfortable. Host was easy to work with - thanks!"
United States
Barbara S.
The price is ¥18,899
¥52,425 total
includes taxes & fees
Nov 17 - Nov 18
Home Sweet Home

11. Blissful Solitude Cottage

Blissful Solitude Cottage
Douglas County
10.0 out of 10, Exceptional, (8 reviews)
"It is a nice place to stay"
United States
Matthew O.
The price is ¥15,544
¥27,305 total
includes taxes & fees
Nov 9 - Nov 10
Blissful Solitude Cottage

12. Orchard House, Orchard House Retreat

Orchard House, Orchard House Retreat
Douglas County
10.0 out of 10, Exceptional, (3 reviews)
"Great little well needed romantic getaway!"
United States
Shawn M.
The price is ¥14,717
¥28,041 total
includes taxes & fees
Nov 8 - Nov 9
Orchard House, Orchard House Retreat
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winston Hotel Reviews

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Winston Vacation Homes information

Number of reviews
224
Accommodation
32 Vacation Homes
Lowest Price
¥18,478
Highest Price
¥57,928