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

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Winston holiday homes

Dining

The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway
Winston
10.0 out of 10, Exceptional, (54 reviews)
"Good hosts & very nice home."
United States
Pamela M.
The price is £287
includes taxes & fees
15 Jul - 16 Jul
The Watusi Place - A Modern Umpqua Valley Getaway
Living area

Home Sweet Home

Home Sweet Home
Sutherlin
9.0 out of 10, Wonderful, (12 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 £264
includes taxes & fees
14 Jul - 15 Jul
Home Sweet Home
Exterior

<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, (105 reviews)
"The Keasington house was perfect for our trip to see family. It had everything we needed. Will definitely be staying again next time we are in the area!"
United States
Michelle C.
The price is £162
includes taxes & fees
16 Jul - 17 Jul
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Terrace/patio

Orchard House, Orchard House Retreat

Orchard House, Orchard House Retreat
Douglas County
10.0 out of 10, Exceptional, (2 reviews)
"Fantastic place to spend the holiday very serene very peaceful"
United States
Gin H.
The price is £152
includes taxes & fees
14 Jul - 15 Jul
Orchard House, Orchard House Retreat
Terrace/patio

Blissful Solitude Cottage

Blissful Solitude Cottage
Douglas County
10.0 out of 10, Exceptional, (8 reviews)
"Clean, beautiful property "
United States
Loyd H.
The price is £159
includes taxes & fees
5 Aug - 6 Aug
Blissful Solitude Cottage
Exterior

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, (41 reviews)
"Nice place, great location."
United States
Gordon
The price is £172
includes taxes & fees
19 Jul - 20 Jul
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Exterior

Downtown Stay at the Red Tiny Twin!

Downtown Stay at the Red Tiny Twin!
Roseburg
9.8 out of 10, Exceptional, (26 reviews)
"It was a perfect place for us to stay for a short trip to visit family with our two little dogs."
United States
Rochelle S.
The price is £134
includes taxes & fees
24 Jul - 25 Jul
Downtown Stay at the Red Tiny Twin!
Exterior detail

Downtown Stay at the Blue Tiny Twin

Downtown Stay at the Blue Tiny Twin
Roseburg
9.6 out of 10, Exceptional, (21 reviews)
"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."
United States
John L.
The price is £134
includes taxes & fees
3 Aug - 4 Aug
Downtown Stay at the Blue Tiny Twin
Exterior

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, (17 reviews)
"Great location, nice and quiet easy to get to fantastic hosts."
United States
Lee and Kristy D.
The price is £116
includes taxes & fees
4 Aug - 5 Aug
Tiny House nestled into the Forest on 160 acre Playground.
Exterior detail

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, (30 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 £152
includes taxes & fees
25 Jul - 26 Jul
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Terrace/patio

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, (25 reviews)
"Amazing B&B. Innkeepers James and Gail were exceptional hosts. Their attention to the details from arrival through departure made our stay very special. Breakfast was delicious. With its many thoughtful amnesties, this Inn has become one of our most memorable. It’s sophisticated, elegant and comfortable!"
United States
karen m.
The price is £211
includes taxes & fees
27 Jul - 28 Jul
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
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

Super 8 by Wyndham Roseburg

Super 8 by Wyndham Roseburg

8/10 Good
"Great indoor pool, so warm. The hotel layout is nice with easy paths out in all directions. It wasn't a fancy place, but it was a very nice place to stay. TV supported HDMI easy. Fridge in room was cool."
gary 1-night trip
Posted 1 hour ago
Super 8 by Wyndham Roseburg

Find out more about Winston

Winston Holiday Homes information

Number of reviews
315
Accommodation
36 Holiday Homes
Lowest Price
£115
Highest Price
£287