Search Vacation Homes in Winston
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Winston vacation homes
The Watusi Place - A Modern Umpqua Valley Getaway
The Watusi Place - A Modern Umpqua Valley GetawayWinston
10.0 out of 10, Exceptional, (54 reviews)
"Good hosts & very nice home."
Pamela M.
The price is AED 661
AED 1,494 total
includes taxes & fees
19 Jul - 20 Jul
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!"
karen m.
The price is AED 907
AED 1,138 total
includes taxes & fees
17 Jul - 18 Jul
Orchard House, Orchard House Retreat
Orchard House, Orchard House RetreatDouglas County
10.0 out of 10, Exceptional, (2 reviews)
"Fantastic place to spend the holiday very serene very peaceful"
Gin H.
The price is AED 447
AED 804 total
includes taxes & fees
19 Jul - 20 Jul
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bathRoseburg
9.8 out of 10, Exceptional, (106 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!"
Michelle C.
The price is AED 441
AED 780 total
includes taxes & fees
22 Jul - 23 Jul
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
The Urban Boho Charmer with Private Backyard, BBQ & HammockRoseburg
9.6 out of 10, Exceptional, (41 reviews)
"Nice place, great location."
Gordon
The price is AED 459
AED 849 total
includes taxes & fees
19 Jul - 20 Jul
Blissful Solitude Cottage
Blissful Solitude CottageDouglas County
10.0 out of 10, Exceptional, (8 reviews)
"Clean, beautiful property "
Loyd H.
The price is AED 440
AED 752 total
includes taxes & fees
5 Aug - 6 Aug
Home Sweet Home
Home Sweet HomeSutherlin
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!"
Barbara S.
The price is AED 441
AED 1,283 total
includes taxes & fees
20 Jul - 21 Jul
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."
Lee and Kristy D.
The price is AED 430
AED 548 total
includes taxes & fees
4 Aug - 5 Aug
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.
Find vacation rentals that suit your style
Private vacation homes
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top Winston Hotel Reviews
Umpqua Valley Hotel
10/10 Excellent
