Title: Winston Vacation Rentals from $112: Search Short-Term Rentals | Expedia.com
[Winston Travel Guide](https://expedia.com/Winston.dx6124402)[Hotels in Winston](https://expedia.com/Winston-Hotels.d6124402.Travel-Guide-Hotels)[Flights to Winston](https://expedia.com/Cheap-Flights-To-Winston.d6124402.Travel-Guide-Flights)[Things to do in Winston](https://expedia.com/Things-To-Do-In-Winston.d6124402.Travel-Guide-Activities)[Car Rentals in Winston](https://expedia.com/Car-Rentals-In-Winston.d6124402.Car-Rental-Guide)[Winston Vacation Packages](https://expedia.com/Winston.d6124402.Destination-Travel-Guides)
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## Check prices for these dates
In two weeks
[Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=6124402&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)
In two months
[May 8 - May 10](https://www.expedia.com/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 three months
[Jun 5 - Jun 7](https://www.expedia.com/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)
In four months
[Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=6124402&startDate=2026-07-03&endDate=2026-07-05&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.com/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.
$337 nightly
$365 total
Mar 18 - Mar 19
Total with taxes and fees
[](https://www.expedia.com/Winston-Hotels-The-Watusi-Place-A-Modern-Umpqua-Valley-Getaway.h78301309.Hotel-Information)
### Bell Sister Flats
[](https://www.expedia.com/Roseburg-Hotels-Bell-Sister-Flats.h106623497.Hotel-Information)
Roseburg
$361 nightly
$396 total
Mar 21 - Mar 22
Total with taxes and fees
[](https://www.expedia.com/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.com/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.
$221 nightly
$242 total
Mar 16 - Mar 17
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Vrbo-Property.h42977823.Hotel-Information)
### Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
[](https://www.expedia.com/Lakefront-Cabin-In-The-Forest-A-Vacation-Wonderland.h105346572.Hotel-Information)
Azalea
9.4/10
Exceptional
(22 reviews)
"Always a pleasure to stay at this property. It is cozy fun place with beautiful surroundings. Anthony is a great host! "
Kai V.
$300 nightly
$305 total
Mar 16 - Mar 17
Total with taxes and fees
[](https://www.expedia.com/Lakefront-Cabin-In-The-Forest-A-Vacation-Wonderland.h105346572.Hotel-Information)
###
\~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
[](https://www.expedia.com/Roseburg-Hotels-BrKeasington-House.h61090454.Hotel-Information)
Roseburg
9.8/10
Exceptional
(92 reviews)
"We had a great stay! The house was amazing, and peaceful. We would definitely stay again. "
Ashley D.
$192 nightly
$210 total
Mar 16 - Mar 17
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-BrKeasington-House.h61090454.Hotel-Information)
### Tiny House nestled into the Forest on 160 acre Playground.
[](https://www.expedia.com/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.
$155 nightly
$158 total
Mar 16 - Mar 17
Total with taxes and fees
[](https://www.expedia.com/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.com/Roseburg-Hotels-Urban-Boho-Charmer.h72546035.Hotel-Information)
Roseburg
9.6/10
Exceptional
(38 reviews)
"Nice place, great location."
Gordon
$206 nightly
$226 total
Mar 16 - Mar 17
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Urban-Boho-Charmer.h72546035.Hotel-Information)
### Private bungalow with AC in charming Roseburg
[](https://www.expedia.com/Roseburg-Hotels-Private-Bungalow-With-AC-In-Charming-Roseburg.h121040727.Hotel-Information)
Roseburg
$347 nightly
$352 total
Mar 16 - Mar 17
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Private-Bungalow-With-AC-In-Charming-Roseburg.h121040727.Hotel-Information)
### Home Sweet Home
[](https://www.expedia.com/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.
$316 nightly
$346 total
Mar 16 - Mar 17
Total with taxes and fees
[](https://www.expedia.com/Sutherlin-Hotels-Home-Sweet-Home.h117931389.Hotel-Information)
### Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
[](https://www.expedia.com/Roseburg-Hotels-Historic-Downtown-Luxurious-Apartment-Only-Steps-Away-From-Local-Restaurants.h38315160.Hotel-Information)
Roseburg
10/10
Exceptional
(3 reviews)
"Terry's place was such a treat! The apartment exceeded so many of our expectations and was perfect for our mini vacation. Wonderful features and amenities. Beautiful finishes, linens and furnishings. Super responsive host. We look forward to our next stay!"
CARISSA F.
$326 nightly
$357 total
Mar 16 - Mar 17
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Historic-Downtown-Luxurious-Apartment-Only-Steps-Away-From-Local-Restaurants.h38315160.Hotel-Information)
### Lil Cedar Lodge
[](https://www.expedia.com/Umpqua-Hotels-Lil-Cedar-Lodge.h111860176.Hotel-Information)
Roseburg
$111 nightly
$112 total
Mar 16 - Mar 17
Total with taxes and fees
[](https://www.expedia.com/Umpqua-Hotels-Lil-Cedar-Lodge.h111860176.Hotel-Information)
### Charming, Private Cottage near I-5 and Golf Course.
[](https://www.expedia.com/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.
$163 nightly
$163 total
Mar 16 - Mar 17
Total with taxes and fees
[](https://www.expedia.com/Myrtle-Creek-Hotels-Charming.h27117565.Hotel-Information)
### A Restful Studio Near a Creek and Forest - Pets
[](https://www.expedia.com/A-Restful-Studio-Near-A-Creek-And-Forest.h99919145.Hotel-Information)
Roseburg
10/10
Exceptional
(43 reviews)
"Enjoyed our stay!"
Dana M.
$165 nightly
$165 total
Mar 26 - Mar 27
Total with taxes and fees
[](https://www.expedia.com/A-Restful-Studio-Near-A-Creek-And-Forest.h99919145.Hotel-Information)
### Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
[](https://www.expedia.com/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.
$166 nightly
$182 total
Mar 16 - Mar 17
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Adorable-2-Bedroom-1-Bath-House-Pet-Friendly-Nearby-Shopping-And-Hospital.h70497599.Hotel-Information)
### Blissful Solitude Cottage
[](https://www.expedia.com/Blissful-Solitude-Cottage.h114429079.Hotel-Information)
Douglas County
10/10
Exceptional
(6 reviews)
"It is a nice place to stay"
Matthew O.
$188 nightly
$190 total
Mar 17 - Mar 18
Total with taxes and fees
[](https://www.expedia.com/Blissful-Solitude-Cottage.h114429079.Hotel-Information)
### Stunning Views\~
Beulaire, a MCM Hillside Retreat Suite.
Beautiful Views\~
[](https://www.expedia.com/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.
$180 nightly
$197 total
Mar 16 - Mar 17
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Beulaire.h59613615.Hotel-Information)
### Orchard House, Orchard House Retreat
[](https://www.expedia.com/Orchard-House.h114429077.Hotel-Information)
Douglas County
10/10
Exceptional
(1 review)
"Fantastic place to spend the holiday very serene very peaceful"
Gin H.
$203 nightly
$205 total
Mar 18 - Mar 19
Total with taxes and fees
[](https://www.expedia.com/Orchard-House.h114429077.Hotel-Information)
### Country Farm Condo w/kitchen, near 7 Feathers Casino on OR Hwy 5; Dog friendly
[](https://www.expedia.com/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
$130 nightly
$132 total
Mar 17 - Mar 18
Total with taxes and fees
[](https://www.expedia.com/Riddle-Hotels-Apartment-On-Christmas-Tree-Farm-Near-7-Feathers-Casino-On-Oregons-Highway-5.h27330105.Hotel-Information)
### Downtown Stay at the Red Tiny Twin!
[](https://www.expedia.com/Roseburg-Hotels-Red-Tiny-Twins.h95850401.Hotel-Information)
Roseburg
9.8/10
Exceptional
(23 reviews)
"It was a perfect place for us to stay for a short trip to visit family with our two little dogs."
Rochelle S.
$156 nightly
$170 total
Mar 16 - Mar 17
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Red-Tiny-Twins.h95850401.Hotel-Information)
### Starry Skies Campout
[](https://www.expedia.com/Starry-Skies-Campout.h114429071.Hotel-Information)
Douglas County
$83 nightly
$84 total
Mar 16 - Mar 17
Total with taxes and fees
[](https://www.expedia.com/Starry-Skies-Campout.h114429071.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.com/Hotel-Search?startDate=2026-03-29&endDate=2026-03-30®ionId=6124402&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)
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Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
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## Find vacation rentals that suit your style
Cabins
[](https://www.expedia.com/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=CABIN)
Private vacation homes
[](https://www.expedia.com/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=VACATION_HOME)
Cottages
[](https://www.expedia.com/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=COTTAGE)
Condos
[](https://www.expedia.com/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=CONDO)
Apartments
[](https://www.expedia.com/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=APARTMENT)
Villas
[](https://www.expedia.com/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=VILLA)
Aparthotels
[](https://www.expedia.com/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=APART_HOTEL)
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## Top Winston Hotel Reviews
### Wolf Creek Inn & Tavern
10/10 Excellent
"We stayed room number 1\. We have stayed many times over the last 7 years. It was our 4th time in room 1\. It was very comfortable and quiet."
[](https://expedia.com/Wolf-Creek-Hotels-Wolf-Creek-Inn-Tavern.h30406572.Hotel-Information)
### Motel 6 Roseburg, OR
6/10 Okay
"There was shopping close by."
[](https://expedia.com/Roseburg-Hotels-Motel-6-Roseburg.h1037746.Hotel-Information)
### Super 8 by Wyndham Roseburg
10/10 Excellent
"Room and staff were great. Disappointed with breakfast, only bagels, cream cheese, juice, instant oatmeal no milk, and coffee. Not a great breakfast, only continiental breakfast."
[](https://expedia.com/Roseburg-Hotels-Super-8-By-Wyndham-Roseburg.h159048.Hotel-Information)
### Comfort Inn Roseburg
8/10 Good
"Safe location, clean rooms, small bathroom, nice staff"
[](https://expedia.com/Roseburg-Hotels-Comfort-Inn.h17750.Hotel-Information)
### Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
10/10 Excellent
"Our stay was wonderful. The house was perfect for our large family. It was very accommodating for our 90 year old parents and our 2 year old granddaughter. It was well stocked, clean and the location is excellent. There was ample room for eveyone and check in/out process was easy. "
[](https://expedia.com/Winston-Hotels-Large-7-Bd-5-Bath-House-A-Few-Miles-From-Wildlife-Safari-Gourmet-Kitchen.h40001956.Hotel-Information)
### SureStay by Best Western Roseburg
10/10 Excellent
"Indoor pool nice "
[](https://expedia.com/Roseburg-Hotels-Sleep-Inn-Suites-Roseburg-North-Near-Medical-Center.h539504.Hotel-Information)
### Best Western Garden Villa Inn
10/10 Excellent
"Yes nice stay "
[](https://expedia.com/Roseburg-Hotels-Best-Western-Garden-Villa-Inn.h7049.Hotel-Information)
### Travelodge by Wyndham Canyonville
6/10 Okay
"Again I find Expedia's rating high. You rated this a 7 and I would judge it to be a 5 or lower. Just another motel offering free breakfast that amounts to coffee, cherrios and yogurt and no place to sit down and eat - must be carried back to room and no tray to carry it on. We checked into motel late afternoon and then went out. Came back around 8PM and found parking lot over flowing. No designated parking spots left. Parked up against fence of neighboring property. If motel was full not sure where you would park. No coffee makings in room and small 10 cup pot in office. No issues with room just the amenities. \*\*\*\* Expedia needs a independent reviewer \*\*\*"
[](https://expedia.com/Canyonville-Hotels-Canyonville-Inn.h84099548.Hotel-Information)
### Best Western Plus Hartford Lodge
10/10 Excellent
"Nice to be able to park next to room"
[](https://expedia.com/Roseburg-Hotels-Best-Western-Plus-Hartford-Lodge.h1784775.Hotel-Information)
## Find out more about Winston
**Everything you need to know about Winston vacation rentals**
Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.
**Winston vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winston in high season.
Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $112 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!
**How to find incredible deals on Winston rentals**
At Expedia, we put the best Winston vacation 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 vacation.
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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- [Vacation Homes in Winston ](https://expedia.com/Winston-Private-Vacation-Homes.d6124402-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Winston ](https://expedia.com/Winston-Apartments.d6124402-aaApartments.Travel-Guide-Accommodation)
- [Motels in Winston ](https://expedia.com/Winston-Motels.d6124402-aaMotels.Travel-Guide-Accommodation)
- [Cottages in Winston ](https://expedia.com/Winston-Cottages.d6124402-aaCottages.Travel-Guide-Accommodation)
- [B&B in Winston ](https://expedia.com/Winston-Bed-And-Breakfast.d6124402-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Cabin Rentals in Winston ](https://expedia.com/Winston-Cabins.d6124402-aaCabins.Travel-Guide-Accommodation)
- [Villas in Winston ](https://expedia.com/Winston-Villas.d6124402-aaVillas.Travel-Guide-Accommodation)
- [Aparthotels in Winston ](https://expedia.com/Winston-Apart-Hotels.d6124402-aaApartHotels.Travel-Guide-Accommodation)
- [RV Parks in Winston ](https://expedia.com/Winston-RV-Parks.d6124402-aaRVParks.Travel-Guide-Accommodation)
- [Resorts in Winston ](https://expedia.com/Winston-Resorts.d6124402-aaResorts.Travel-Guide-Accommodation)
- [Farmstay in Winston ](https://expedia.com/Winston-Agritourism.d6124402-aaAgritourism.Travel-Guide-Accommodation)
- [Guest Houses in Winston ](https://expedia.com/Winston-Guest-Houses.d6124402-aaGuestHouses.Travel-Guide-Accommodation)
- [Condo Rentals in Winston ](https://expedia.com/Winston-Condos.d6124402-aaCondos.Travel-Guide-Accommodation)
## Frequently asked questions
### Are there vacation rentals in Winston?
### What's the top vacation rental in Winston?
### How many vacation rentals will I find in Winston?
### What’s there to see and do in Winston?
### What’s a vacation rental in Winston like?
### Expedia's Latest Trends
Hotels
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Flights
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- [Flights to MFR](https://expedia.com/Cheap-Flights-To-Medford.d602702.Travel-Guide-Flights)
- [Flights to RDM](https://expedia.com/Cheap-Flights-To-Bend.d6051534.Travel-Guide-Flights)
Cars
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Vacation Rentals
- [Seaside Short Term Rentals](https://expedia.com/Seaside-Vacation-Rentals.d6179.Travel-Guide-VacationRentals)
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