Title: Holiday Rentals Winston from £111: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk
[Hotels in Winston](https://expedia.co.uk/Winston-Hotels.d6124402.Travel-Guide-Hotels)[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 rentals
### 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.
£272
includes taxes & fees
20 Feb - 21 Feb
[](https://www.expedia.co.uk/Winston-Hotels-The-Watusi-Place-A-Modern-Umpqua-Valley-Getaway.h78301309.Hotel-Information)
### Charming cottage studio in serene environment perfect for a relaxing getaway
[](https://www.expedia.co.uk/Winston-Hotels-Charming-Cottage-Studio-In-Serene-Environment-Perfect-For-A-Relaxing-Getaway.h119289988.Hotel-Information)
Winston
£136
includes taxes & fees
20 Feb - 21 Feb
[](https://www.expedia.co.uk/Winston-Hotels-Charming-Cottage-Studio-In-Serene-Environment-Perfect-For-A-Relaxing-Getaway.h119289988.Hotel-Information)
### Lil Cedar Lodge
[](https://www.expedia.co.uk/Umpqua-Hotels-Lil-Cedar-Lodge.h111860176.Hotel-Information)
Roseburg
£85
includes taxes & fees
12 Feb - 13 Feb
[](https://www.expedia.co.uk/Umpqua-Hotels-Lil-Cedar-Lodge.h111860176.Hotel-Information)
### Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
[](https://www.expedia.co.uk/Lakefront-Cabin-In-The-Forest-A-Vacation-Wonderland.h105346572.Hotel-Information)
Azalea
9.4/10
Exceptional
(22 reviews)
"Wonderful and peaceful place to stay! Breakfast accommodations were above and beyond and such a pleasant surprise! Highly recommend this cute place!"
Connie H.
£229
includes taxes & fees
12 Feb - 13 Feb
[](https://www.expedia.co.uk/Lakefront-Cabin-In-The-Forest-A-Vacation-Wonderland.h105346572.Hotel-Information)
### Charming, Private Cottage near I-5 and Golf Course.
[](https://www.expedia.co.uk/Myrtle-Creek-Hotels-Charming.h27117565.Hotel-Information)
Myrtle Creek
10/10
Exceptional
(42 reviews)
"This is the second time I have stayed here, both times with my dog. The place is convenient, quiet, clean, comfortable, and with great touches and landscaping outside. Wonderful place."
Carter L.
£134
includes taxes & fees
20 Feb - 21 Feb
[](https://www.expedia.co.uk/Myrtle-Creek-Hotels-Charming.h27117565.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
12 Feb - 13 Feb
[](https://www.expedia.co.uk/Roseburg-Hotels-BrKeasington-House.h61090454.Hotel-Information)
### Country Farm Condo, near 7 Feathers Casino/Canyonville on OR Hwy 5; Dog friendly
[](https://www.expedia.co.uk/Riddle-Hotels-Apartment-On-Christmas-Tree-Farm-Near-7-Feathers-Casino-On-Oregons-Highway-5.h27330105.Hotel-Information)
Riddle
9.8/10
Exceptional
(90 reviews)
"My wife and I travel a lot with our little dachshund. This property is one of the nicest private offerings we have ever experienced. The owner has created a perfectly lovely and cozy little apartment for two. It is completely stocked and meticulously well-organized. The owner is also gracious and very flexible. An ideal place to stay."
Dale
£111
includes taxes & fees
13 Feb - 14 Feb
[](https://www.expedia.co.uk/Riddle-Hotels-Apartment-On-Christmas-Tree-Farm-Near-7-Feathers-Casino-On-Oregons-Highway-5.h27330105.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)
### 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
£171
includes taxes & fees
8 Mar - 9 Mar
[](https://www.expedia.co.uk/Roseburg-Hotels-Urban-Boho-Charmer.h72546035.Hotel-Information)
### Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
[](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.
[](https://www.expedia.co.uk/Roseburg-Hotels-Modern-Westside-3BR-Bungalow-W-Private-Backyard.h83630896.Hotel-Information)
### Bell Sister Flats
[](https://www.expedia.co.uk/Roseburg-Hotels-Bell-Sister-Flats.h106623497.Hotel-Information)
Roseburg
£293
includes taxes & fees
12 Feb - 13 Feb
[](https://www.expedia.co.uk/Roseburg-Hotels-Bell-Sister-Flats.h106623497.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.
£179
includes taxes & fees
12 Feb - 13 Feb
[](https://www.expedia.co.uk/Roseburg-Hotels-Luxury.h42977823.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
£131
includes taxes & fees
12 Feb - 13 Feb
[](https://www.expedia.co.uk/Blissful-Solitude-Cottage.h114429079.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.
£139
includes taxes & fees
12 Feb - 13 Feb
[](https://www.expedia.co.uk/Orchard-House.h114429077.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
22 Feb - 23 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.
£258
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
8 Mar - 9 Mar
[](https://www.expedia.co.uk/Roseburg-Hotels-Beulaire.h59613615.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.
£118
includes taxes & fees
12 Feb - 13 Feb
[](https://www.expedia.co.uk/Umpqua-Hotels-Tiny-House-Nestled-Into-The-Forest-On-160-Acre-Playground.h96842207.Hotel-Information)
### Starry Skies Campout
[](https://www.expedia.co.uk/Starry-Skies-Campout.h114429071.Hotel-Information)
Douglas County
£65
includes taxes & fees
12 Feb - 13 Feb
[](https://www.expedia.co.uk/Starry-Skies-Campout.h114429071.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
12 Feb - 13 Feb
[](https://www.expedia.co.uk/Roseburg-Hotels-Red-Tiny-Twins.h95850401.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=2026-02-25&endDate=2026-02-26®ionId=6124402&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)
## 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=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&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=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&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=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=APART_HOTEL)
Condos
[](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=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=CONDO)
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=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&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=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&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=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&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)
### 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)
### Travelodge by Wyndham Canyonville
10/10 Excellent
"Excellent service and Rooms "
[](https://expedia.co.uk/Canyonville-Hotels-Canyonville-Inn.h84099548.Hotel-Information)
## Find out more about Winston
**Everything you need to know about** **Winston** **holiday rentals**
Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winston holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/Villas)... The list goes on, and on… and on!
There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winston holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.
**Winston holiday rentals: An excellent choice for every season**
Whenever you want to travel, a warm welcome awaits you in Winston. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .
Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winston holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Winston holiday rentals we have selected for you start as low as £111 per night. Entering your travel dates in the search wizard you might find even better deals!
**How to find incredible deals on Winston rentals**
At Expedia, we put the best Winston holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.
To find some top Winston rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winston holiday.
If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.
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- [Wales Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Wales.d11220.Holiday-Rental-Destinations)
- [Northern Ireland Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Northern-Ireland.d11221.Holiday-Rental-Destinations)
## Frequently asked questions
### Are there holiday rentals in Winston?
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