Title: Winston Vacation Rentals from CA $156: Short-Term Rentals for 2026 | Expedia.ca
[Hotels in Winston](https://expedia.ca/Winston-Hotels.d6124402.Travel-Guide-Hotels)[Flights to Winston](https://expedia.ca/Cheap-Flights-To-Winston.d6124402.Travel-Guide-Flights)[Things to do in Winston](https://expedia.ca/Things-To-Do-In-Winston.d6124402.Travel-Guide-Activities)[Winston Car Rentals](https://expedia.ca/Car-Rentals-In-Winston.d6124402.Car-Rental-Guide)[Winston Vacation Packages](https://expedia.ca/Winston.d6124402.Destination-Travel-Guides)
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## Check prices for these dates
In two weeks
[Apr 10 - Apr 12](https://www.expedia.ca/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 two months
[May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=6124402&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)
In three months
[Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=6124402&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)
In four months
[Jul 17 - Jul 19](https://www.expedia.ca/Hotel-Search?regionId=6124402&startDate=2026-07-17&endDate=2026-07-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)
## Our top choices for Winston vacation rentals
### The Watusi Place - A Modern Umpqua Valley Getaway
[](https://www.expedia.ca/Winston-Hotels-The-Watusi-Place-A-Modern-Umpqua-Valley-Getaway.h78301309.Hotel-Information)
Winston
10/10
Exceptional
(50 reviews)
"Home was well stocked and was very accessible to our winery we belong to. "
Amy W.
CA $224
CA $531 total
includes taxes & fees
Apr 3 - Apr 4
[](https://www.expedia.ca/Winston-Hotels-The-Watusi-Place-A-Modern-Umpqua-Valley-Getaway.h78301309.Hotel-Information)
### Lil Cedar Lodge
[](https://www.expedia.ca/Umpqua-Hotels-Lil-Cedar-Lodge.h111860176.Hotel-Information)
Roseburg
10/10
Exceptional
(1 review)
CA $119
CA $156 total
includes taxes & fees
Mar 29 - Mar 30
[](https://www.expedia.ca/Umpqua-Hotels-Lil-Cedar-Lodge.h111860176.Hotel-Information)
### Charming, Private Cottage near I-5 and Golf Course.
[](https://www.expedia.ca/Myrtle-Creek-Hotels-Charming.h27117565.Hotel-Information)
Myrtle Creek
10/10
Exceptional
(43 reviews)
"Ken & Anya really know how to provide amenities to give warmth and a sense of home. The cottage was simply amazing and we'll be back!"
Robert J.
CA $199
CA $227 total
includes taxes & fees
Mar 30 - Mar 31
[](https://www.expedia.ca/Myrtle-Creek-Hotels-Charming.h27117565.Hotel-Information)
### A Restful Studio Near a Creek and Forest - Pets
[](https://www.expedia.ca/A-Restful-Studio-Near-A-Creek-And-Forest.h99919145.Hotel-Information)
Roseburg
10/10
Exceptional
(43 reviews)
"Enjoyed our stay!"
Dana M.
CA $152
CA $254 total
includes taxes & fees
Apr 2 - Apr 3
[](https://www.expedia.ca/A-Restful-Studio-Near-A-Creek-And-Forest.h99919145.Hotel-Information)
### Blissful Solitude Cottage
[](https://www.expedia.ca/Blissful-Solitude-Cottage.h114429079.Hotel-Information)
Douglas County
10/10
Exceptional
(6 reviews)
"It is a nice place to stay"
Matthew O.
CA $136
CA $251 total
includes taxes & fees
Mar 29 - Mar 30
[](https://www.expedia.ca/Blissful-Solitude-Cottage.h114429079.Hotel-Information)
### Tiny House nestled into the Forest on 160 acre Playground.
[](https://www.expedia.ca/Umpqua-Hotels-Tiny-House-Nestled-Into-The-Forest-On-160-Acre-Playground.h96842207.Hotel-Information)
Roseburg
9.6/10
Exceptional
(14 reviews)
"Wonderful environment and very peaceful stay. "
Sarah C.
CA $160
CA $219 total
includes taxes & fees
Mar 29 - Mar 30
[](https://www.expedia.ca/Umpqua-Hotels-Tiny-House-Nestled-Into-The-Forest-On-160-Acre-Playground.h96842207.Hotel-Information)
###
\~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
[](https://www.expedia.ca/Roseburg-Hotels-BrKeasington-House.h61090454.Hotel-Information)
Roseburg
9.8/10
Exceptional
(93 reviews)
"Host was absolutely fantastic in assisting us with making sure our stay was perfect and peaceful we throughly enjoyed our stay the facilities were perfect for home cooked breakfast and a small family gathering to celebrate Christmas with our grandkids and kids Awill put as a favorite foe our next trip cant say thank you enough."
Brenda L.
[](https://www.expedia.ca/Roseburg-Hotels-BrKeasington-House.h61090454.Hotel-Information)
### Country Farm Condo w/kitchen, near 7 Feathers Casino on OR Hwy 5; Dog friendly
[](https://www.expedia.ca/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
CA $104
CA $183 total
includes taxes & fees
Apr 1 - Apr 2
[](https://www.expedia.ca/Riddle-Hotels-Apartment-On-Christmas-Tree-Farm-Near-7-Feathers-Casino-On-Oregons-Highway-5.h27330105.Hotel-Information)
### Downtown Stay at the Blue Tiny Twin
[](https://www.expedia.ca/Roseburg-Hotels-Blue-Downtown-Stay-Eco-Pet-Friendly-Tiny-Twins.h93828604.Hotel-Information)
Roseburg
9.4/10
Exceptional
(19 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."
John L.
CA $132
CA $251 total
includes taxes & fees
Apr 26 - Apr 27
[](https://www.expedia.ca/Roseburg-Hotels-Blue-Downtown-Stay-Eco-Pet-Friendly-Tiny-Twins.h93828604.Hotel-Information)
### The Urban Boho Charmer with Private Backyard, BBQ & Hammock
[](https://www.expedia.ca/Roseburg-Hotels-Urban-Boho-Charmer.h72546035.Hotel-Information)
Roseburg
9.6/10
Exceptional
(39 reviews)
"Nice place, great location."
Gordon
CA $173
CA $320 total
includes taxes & fees
Mar 30 - Mar 31
[](https://www.expedia.ca/Roseburg-Hotels-Urban-Boho-Charmer.h72546035.Hotel-Information)
### Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
[](https://www.expedia.ca/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.
CA $277
CA $461 total
includes taxes & fees
Apr 22 - Apr 23
[](https://www.expedia.ca/Lakefront-Cabin-In-The-Forest-A-Vacation-Wonderland.h105346572.Hotel-Information)
### Orchard House, Orchard House Retreat
[](https://www.expedia.ca/Orchard-House.h114429077.Hotel-Information)
Douglas County
10/10
Exceptional
(1 review)
"Fantastic place to spend the holiday very serene very peaceful"
Gin H.
CA $137
CA $267 total
includes taxes & fees
Mar 29 - Mar 30
[](https://www.expedia.ca/Orchard-House.h114429077.Hotel-Information)
### Stunning Views\~
Beulaire, a MCM Hillside Retreat Suite.
Beautiful Views\~
[](https://www.expedia.ca/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.
CA $153
CA $275 total
includes taxes & fees
Mar 29 - Mar 30
[](https://www.expedia.ca/Roseburg-Hotels-Beulaire.h59613615.Hotel-Information)
### Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
[](https://www.expedia.ca/Roseburg-Hotels-Vrbo-Property.h42977823.Hotel-Information)
Roseburg
10/10
Exceptional
(24 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.
CA $269
CA $334 total
includes taxes & fees
Mar 29 - Mar 30
[](https://www.expedia.ca/Roseburg-Hotels-Vrbo-Property.h42977823.Hotel-Information)
### Bell Sister Flats
[](https://www.expedia.ca/Roseburg-Hotels-Bell-Sister-Flats.h106623497.Hotel-Information)
Roseburg
CA $393
CA $537 total
includes taxes & fees
Apr 12 - Apr 13
[](https://www.expedia.ca/Roseburg-Hotels-Bell-Sister-Flats.h106623497.Hotel-Information)
### Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
[](https://www.expedia.ca/Roseburg-Hotels-Adorable-2-Bedroom-1-Bath-House-Pet-Friendly-Nearby-Shopping-And-Hospital.h70497599.Hotel-Information)
Roseburg
9.6/10
Exceptional
(54 reviews)
"It certainly is adorable, well-kept, well-stocked. We would love to stay here again!"
Faith S.
CA $153
CA $251 total
includes taxes & fees
Mar 29 - Mar 30
[](https://www.expedia.ca/Roseburg-Hotels-Adorable-2-Bedroom-1-Bath-House-Pet-Friendly-Nearby-Shopping-And-Hospital.h70497599.Hotel-Information)
### Starry Skies Campout
[](https://www.expedia.ca/Starry-Skies-Campout.h114429071.Hotel-Information)
Douglas County
CA $87
CA $117 total
includes taxes & fees
Apr 5 - Apr 6
[](https://www.expedia.ca/Starry-Skies-Campout.h114429071.Hotel-Information)
### Downtown Stay at the Red Tiny Twin!
[](https://www.expedia.ca/Roseburg-Hotels-Red-Tiny-Twins.h95850401.Hotel-Information)
Roseburg
9.8/10
Exceptional
(24 reviews)
"It was a perfect place for us to stay for a short trip to visit family with our two little dogs."
Rochelle S.
CA $118
CA $236 total
includes taxes & fees
Mar 30 - Mar 31
[](https://www.expedia.ca/Roseburg-Hotels-Red-Tiny-Twins.h95850401.Hotel-Information)
### Madrone Hideout, Madrone Hideout Chariot
[](https://www.expedia.ca/Madrone-Hideout.h114429068.Hotel-Information)
Douglas County
CA $160
CA $294 total
includes taxes & fees
Apr 19 - Apr 20
[](https://www.expedia.ca/Madrone-Hideout.h114429068.Hotel-Information)
### Private bungalow with AC in charming Roseburg
[](https://www.expedia.ca/Roseburg-Hotels-Private-Bungalow-With-AC-In-Charming-Roseburg.h121040727.Hotel-Information)
Roseburg
CA $420
CA $488 total
includes taxes & fees
Apr 5 - Apr 6
[](https://www.expedia.ca/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.ca/Hotel-Search?startDate=2026-04-11&endDate=2026-04-12®ionId=6124402&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)
## Find vacation rentals that suit your style
Private vacation homes
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Cabins
[](https://www.expedia.ca/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=CABIN)
Cottages
[](https://www.expedia.ca/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=COTTAGE)
Apartments
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Aparthotels
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Villas
[](https://www.expedia.ca/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=VILLA)
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## Top Winston Hotel Reviews
### Motel 6 Sutherlin, OR
4/10 Poor
"The mattress on the bed was very hard and uncomfortable did not make for a good sleep "
[](https://expedia.ca/Roseburg-Hotels-Motel-6-Sutherlin.h425916.Hotel-Information)
### Rosewood Inn and Suites
2/10 Terrible
"I booked this room last minute to get my wife and 2 kids off the road during a long road trip. Front desk, I'm assuming the manager, was rude about my wife's service dog and claimed to have no knowledge of it. I made two references to the dog in my message to hotel on the Expedia site when booking the room. Once they got the room, which was disgusting, dirty, and stained. There were NO BLANKETS! When my wife asked about blankets the manager was confrontational and rude. He eventually brought ONE TINY BLANKET, dirty and with cigarette burn holes. It was 40 degrees out and the heat had not been running in that room.THIS WAS A TWO BED ROOM, where is the 2nd blanket? My wife was scared to make any more requests of this person due to their poor service and reaction to a basic request."
[](https://expedia.ca/Roseburg-Hotels-Rosewood-Inn-And-Suites.h919945.Hotel-Information)
### Umpqua Valley Hotel
10/10 Excellent
"Very nice people and the food was very good "
[](https://expedia.ca/Roseburg-Hotels-Umpqua-Valley-Hotel.h24153680.Hotel-Information)
### The Lodge at Roseburg
6/10 Okay
"My only complaint was pipes in tub had a bad smell when water ran down from shower and plug was broke off so couldn't close it. Also soap dispenser was stripped from wall making it hard to get soap out. "
[](https://expedia.ca/Roseburg-Hotels-Holiday-Inn-Express-Roseburg.h22705.Hotel-Information)
### Best Western Garden Villa Inn
8/10 Good
"A very short stay, got in at 9pm and left at 8am. The room was small but clean and roomy enough. It had all the necessities although the little shampoo and conditioner bottles are really for one person. The bed had nice sheets and there was an extra blanket if needed. The bed was on the hard side though. The breakfast buffet was amazing and the staff was very friendly and kind. Only drawback is the hotel is in between 2 freeways and if it wasn’t for having earplugs , I would have had a hard time getting to sleep. Overall it’s a nice hotel for the price we paid and would stay again. "
[](https://expedia.ca/Roseburg-Hotels-Best-Western-Garden-Villa-Inn.h7049.Hotel-Information)
### Wolf Creek Inn & Tavern
10/10 Excellent
"Great staff, great vibe! EV charger on site."
[](https://expedia.ca/Wolf-Creek-Hotels-Wolf-Creek-Inn-Tavern.h30406572.Hotel-Information)
### Best Western Plus Hartford Lodge
8/10 Good
"Nice hotel "
[](https://expedia.ca/Roseburg-Hotels-Best-Western-Plus-Hartford-Lodge.h1784775.Hotel-Information)
### Motel 6 Roseburg, OR
10/10 Excellent
"Clean, well-maintained, good food right next door. Parking lot was spacious enough to accommodate a 15 foot moving truck with no concerns about security."
[](https://expedia.ca/Roseburg-Hotels-Motel-6-Roseburg.h1037746.Hotel-Information)
### SureStay by Best Western Roseburg
8/10 Good
"The staff was incredibly friendly and accommodating the hotel was also a good price. I didn't like that the breakfast area was closed except during breakfast hours. It's nice to have somewhere to sit and/or eat meals of your own outside of the room. The dining area was also super small, but it sounds like they are working on expanding that. The pool was nice "
[](https://expedia.ca/Roseburg-Hotels-Sleep-Inn-Suites-Roseburg-North-Near-Medical-Center.h539504.Hotel-Information)
## Find out more about Winston
You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winston. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.
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- [Resorts in Winston ](https://expedia.ca/Winston-Resort-Hotels.d6124402-aaResortHotels.Travel-Guide-Accommodation)
- [Inns in Winston ](https://expedia.ca/Winston-Inns.d6124402-aaInns.Travel-Guide-Accommodation)
- [Guest Houses in Winston ](https://expedia.ca/Winston-Guest-Houses.d6124402-aaGuestHouses.Travel-Guide-Accommodation)
- [Condo Rentals in Winston ](https://expedia.ca/Winston-Condos.d6124402-aaCondos.Travel-Guide-Accommodation)
## Frequently asked questions
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