Title: Winston Holiday Homes from £124: Search Holiday Homes in Winston | Expedia.co.uk
[Hotels in Winston](https://expedia.co.uk/Winston-Hotels.d6124402.Travel-Guide-Hotels)[Holiday Rentals in Winston](https://expedia.co.uk/Winston-Holiday-Rentals.d6124402.Travel-Guide-HolidayRentals)[Flights to Winston](https://expedia.co.uk/Cheap-Flights-To-Winston.d6124402.Travel-Guide-Flights)[Winston Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Winston.d6124402.Car-Hire-Guide)[Winston Holidays](https://expedia.co.uk/Winston.d6124402.Holidays-City-Breaks)
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## Check prices for these dates
In two weeks
[27 Feb - 1 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=6124402&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)
In two months
[10 Apr - 12 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=6124402&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)
In three months
[8 May - 10 May](https://www.expedia.co.uk/Hotel-Search?regionId=6124402&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)
In four months
[5 Jun - 7 Jun](https://www.expedia.co.uk/Hotel-Search?regionId=6124402&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)
## Our top choices for Winston holiday homes
### The Watusi Place - A Modern Umpqua Valley Getaway
[](https://www.expedia.co.uk/Winston-Hotels-The-Watusi-Place-A-Modern-Umpqua-Valley-Getaway.h78301309.Hotel-Information)
Winston
10/10
Exceptional
(48 reviews)
"The house was amazing! Easy to get in, clean and well stocked. Definitely recommend to anyone looking for a nice place."
Amy H.
£274
includes taxes & fees
13 Feb - 14 Feb
[](https://www.expedia.co.uk/Winston-Hotels-The-Watusi-Place-A-Modern-Umpqua-Valley-Getaway.h78301309.Hotel-Information)
### Orchard House, Orchard House Retreat
[](https://www.expedia.co.uk/Orchard-House.h114429077.Hotel-Information)
Douglas County
10/10
Exceptional
(1 review)
"Fantastic place to spend the holiday very serene very peaceful"
Gin H.
£148
includes taxes & fees
18 Feb - 19 Feb
[](https://www.expedia.co.uk/Orchard-House.h114429077.Hotel-Information)
### A Restful Studio Near a Creek and Forest - Pets
[](https://www.expedia.co.uk/A-Restful-Studio-Near-A-Creek-And-Forest.h99919145.Hotel-Information)
Roseburg
10/10
Exceptional
(42 reviews)
"Enjoyed our stay!"
Dana M.
£124
includes taxes & fees
23 Feb - 24 Feb
[](https://www.expedia.co.uk/A-Restful-Studio-Near-A-Creek-And-Forest.h99919145.Hotel-Information)
### Modern Mid-Century Retreat with Stylish Amenities & Family-Friendly Comfort
[](https://www.expedia.co.uk/Roseburg-Hotels-Modern-Westside-3BR-Bungalow-W-Private-Backyard.h83630896.Hotel-Information)
Roseburg
9.8/10
Exceptional
(39 reviews)
"We had a great stay while we visited family. The house had everything we needed, and the new mattresses were very comfortable. Gary was easy to get ahold of and responded quickly. We would stay again. "
Riley E.
£218
includes taxes & fees
15 Feb - 16 Feb
[](https://www.expedia.co.uk/Roseburg-Hotels-Modern-Westside-3BR-Bungalow-W-Private-Backyard.h83630896.Hotel-Information)
### Blissful Solitude Cottage
[](https://www.expedia.co.uk/Blissful-Solitude-Cottage.h114429079.Hotel-Information)
Douglas County
10/10
Exceptional
(4 reviews)
"My trip actually got canceled last minute, but the communication with the host was absolutely amazing and I will absolutely rebook as soon as possible"
steve
£139
includes taxes & fees
16 Feb - 17 Feb
[](https://www.expedia.co.uk/Blissful-Solitude-Cottage.h114429079.Hotel-Information)
### Tiny House nestled into the Forest on 160 acre Playground.
[](https://www.expedia.co.uk/Umpqua-Hotels-Tiny-House-Nestled-Into-The-Forest-On-160-Acre-Playground.h96842207.Hotel-Information)
Roseburg
9.6/10
Exceptional
(13 reviews)
"Wonderful environment and very peaceful stay. "
Sarah C.
£128
includes taxes & fees
6 Mar - 7 Mar
[](https://www.expedia.co.uk/Umpqua-Hotels-Tiny-House-Nestled-Into-The-Forest-On-160-Acre-Playground.h96842207.Hotel-Information)
### The Urban Boho Charmer with Private Backyard, BBQ & Hammock
[](https://www.expedia.co.uk/Roseburg-Hotels-Urban-Boho-Charmer.h72546035.Hotel-Information)
Roseburg
9.6/10
Exceptional
(37 reviews)
"Nice place, great location."
Gordon
£170
includes taxes & fees
13 Feb - 14 Feb
[](https://www.expedia.co.uk/Roseburg-Hotels-Urban-Boho-Charmer.h72546035.Hotel-Information)
### Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
[](https://www.expedia.co.uk/Roseburg-Hotels-Luxury.h42977823.Hotel-Information)
Roseburg
10/10
Exceptional
(24 reviews)
"Absolutely the most delightful and magical place to stay! Wonderfully gracious hosts! They made our honeymoon stay spectacular and special! James and Gail are fabulous. We had the most incredible breakfast as well. We felt like royalty! "
Rachel S.
£180
includes taxes & fees
14 Feb - 15 Feb
[](https://www.expedia.co.uk/Roseburg-Hotels-Luxury.h42977823.Hotel-Information)
### Downtown Stay at the Red Tiny Twin!
[](https://www.expedia.co.uk/Roseburg-Hotels-Red-Tiny-Twins.h95850401.Hotel-Information)
Roseburg
9.8/10
Exceptional
(21 reviews)
"It was a perfect place for us to stay for a short trip to visit family with our two little dogs."
Rochelle S.
£135
includes taxes & fees
13 Feb - 14 Feb
[](https://www.expedia.co.uk/Roseburg-Hotels-Red-Tiny-Twins.h95850401.Hotel-Information)
###
\~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
[](https://www.expedia.co.uk/Roseburg-Hotels-BrKeasington-House.h61090454.Hotel-Information)
Roseburg
9.8/10
Exceptional
(91 reviews)
"We had a great stay! The house was amazing, and peaceful. We would definitely stay again. "
Ashley D.
£156
includes taxes & fees
13 Feb - 14 Feb
[](https://www.expedia.co.uk/Roseburg-Hotels-BrKeasington-House.h61090454.Hotel-Information)
### Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
[](https://www.expedia.co.uk/Roseburg-Hotels-Adorable-2-Bedroom-1-Bath-House-Pet-Friendly-Nearby-Shopping-And-Hospital.h70497599.Hotel-Information)
Roseburg
9.6/10
Exceptional
(53 reviews)
"It certainly is adorable, well-kept, well-stocked. We would love to stay here again!"
Faith S.
£135
includes taxes & fees
13 Feb - 14 Feb
[](https://www.expedia.co.uk/Roseburg-Hotels-Adorable-2-Bedroom-1-Bath-House-Pet-Friendly-Nearby-Shopping-And-Hospital.h70497599.Hotel-Information)
### Home Sweet Home
[](https://www.expedia.co.uk/Sutherlin-Hotels-Home-Sweet-Home.h117931389.Hotel-Information)
Sutherlin
8.6/10
Excellent
(10 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.
£259
includes taxes & fees
19 Feb - 20 Feb
[](https://www.expedia.co.uk/Sutherlin-Hotels-Home-Sweet-Home.h117931389.Hotel-Information)
### Stunning Views\~
Beulaire, a MCM Hillside Retreat Suite.
Beautiful Views\~
[](https://www.expedia.co.uk/Roseburg-Hotels-Beulaire.h59613615.Hotel-Information)
Roseburg
9.6/10
Exceptional
(29 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."
Nicole B.
£148
includes taxes & fees
13 Feb - 14 Feb
[](https://www.expedia.co.uk/Roseburg-Hotels-Beulaire.h59613615.Hotel-Information)
### Private bungalow with AC in charming Roseburg
[](https://www.expedia.co.uk/Roseburg-Hotels-Private-Bungalow-With-AC-In-Charming-Roseburg.h121040727.Hotel-Information)
Roseburg
£257
includes taxes & fees
25 Feb - 26 Feb
[](https://www.expedia.co.uk/Roseburg-Hotels-Private-Bungalow-With-AC-In-Charming-Roseburg.h121040727.Hotel-Information)
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.
[View all properties](https://expedia.co.uk/Hotel-Search?startDate=2026-02-26&endDate=2026-02-27®ionId=6124402&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)
##
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## Find holiday rentals that suit your style
Apartments
[](https://www.expedia.co.uk/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=APARTMENT)
Private holiday homes
[](https://www.expedia.co.uk/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=VACATION_HOME)
Aparthotels
[](https://www.expedia.co.uk/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=APART_HOTEL)
Cottages
[](https://www.expedia.co.uk/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=COTTAGE)
Cabins
[](https://www.expedia.co.uk/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=CABIN)
Villas
[](https://www.expedia.co.uk/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=VILLA)
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## Top Winston Hotel Reviews
### Riverfront Inn Roseburg
10/10 Excellent
"The room was clean and the staff were very friendly."
[](https://expedia.co.uk/Roseburg-Hotels-Riverfront-Inn-Roseburg.h16066.Hotel-Information)
### Hampton Inn & Suites Roseburg
10/10 Excellent
"I really enjoyed staying the night at this hotel. Everyone at the front desk was so sweet and kind. I am senior solo traveler, and I felt very safe on my own in this hotel. The parking lot is safe. The breakfast was really good. Lots of choices from hot food to cold cereal."
[](https://expedia.co.uk/Roseburg-Hotels-Hampton-Inn-Suites-Roseburg.h22270751.Hotel-Information)
### Wolf Creek Inn & Tavern
10/10 Excellent
"Great staff, historic surroundings, and good food."
[](https://expedia.co.uk/Wolf-Creek-Hotels-Wolf-Creek-Inn-Tavern.h30406572.Hotel-Information)
### SureStay by Best Western Roseburg
10/10 Excellent
"The room was very clean and the beds were comfy. The shower was so nice! Staff was great. Breakfast was good also."
[](https://expedia.co.uk/Roseburg-Hotels-Sleep-Inn-Suites-Roseburg-North-Near-Medical-Center.h539504.Hotel-Information)
### Comfort Inn Roseburg
10/10 Excellent
"First room would be a 3+ the bed was hard. We told the receptionist and they moved us to a room that the Bed was comfy. Breakfast was pretty good. Waffles were yummy but the verity want there. Nice people to work with. "
[](https://expedia.co.uk/Roseburg-Hotels-Comfort-Inn.h17750.Hotel-Information)
### Holiday Inn Express Roseburg by IHG
10/10 Excellent
"The room was fantastic, a king suite which suited my disability perfectly. The pool and hot tub were spotless. The staff was helpful with all requests "
[](https://expedia.co.uk/Roseburg-Hotels-Holiday-Inn-Express-Roseburg.h22705.Hotel-Information)
### Motel 6 Roseburg, OR
10/10 Excellent
"Yes it was perfect"
[](https://expedia.co.uk/Roseburg-Hotels-Motel-6-Roseburg.h1037746.Hotel-Information)
### Super 8 by Wyndham Roseburg
10/10 Excellent
"Clean room,courteous staff, pleasant stay"
[](https://expedia.co.uk/Roseburg-Hotels-Super-8-By-Wyndham-Roseburg.h159048.Hotel-Information)
### Motel 6 Sutherlin, OR
10/10 Excellent
"Dawn is the Best in the West!!"
[](https://expedia.co.uk/Roseburg-Hotels-Motel-6-Sutherlin.h425916.Hotel-Information)
## Find out more about Winston
## Winston Holiday Homes information
| Number of reviews | 368 |
| ----------------- | ---------------- |
| Accommodation | 43 Holiday Homes |
| Lowest Price | £124 |
| Highest Price | £274 |
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