Title: Winchester Vacation Rentals from CA $154: Short-Term Rentals for 2026 | Expedia.ca
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## Check prices for these dates
In two weeks
[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=12104&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)
In two months
[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=12104&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)
In three months
[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=12104&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)
In four months
[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=12104&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)
## Our top choices for Winchester vacation rentals
### 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
(42 reviews)
"Enjoyed our stay!"
Dana M.
CA $130
CA $227 total
includes taxes & fees
Feb 23 - Feb 24
[](https://www.expedia.ca/A-Restful-Studio-Near-A-Creek-And-Forest.h99919145.Hotel-Information)
### Lil Cedar Lodge
[](https://www.expedia.ca/Umpqua-Hotels-Lil-Cedar-Lodge.h111860176.Hotel-Information)
Roseburg
CA $117
CA $154 total
includes taxes & fees
Feb 8 - Feb 9
[](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
(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.
CA $219
CA $248 total
includes taxes & fees
Feb 9 - Feb 10
[](https://www.expedia.ca/Myrtle-Creek-Hotels-Charming.h27117565.Hotel-Information)
### Home Sweet Home
[](https://www.expedia.ca/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.
CA $164
CA $476 total
includes taxes & fees
Feb 21 - Feb 22
[](https://www.expedia.ca/Sutherlin-Hotels-Home-Sweet-Home.h117931389.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
(13 reviews)
"Wonderful environment and very peaceful stay. "
Sarah C.
CA $158
CA $216 total
includes taxes & fees
Feb 7 - Feb 8
[](https://www.expedia.ca/Umpqua-Hotels-Tiny-House-Nestled-Into-The-Forest-On-160-Acre-Playground.h96842207.Hotel-Information)
### Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
[](https://www.expedia.ca/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.
CA $135
CA $392 total
includes taxes & fees
Feb 9 - Feb 10
[](https://www.expedia.ca/Roseburg-Hotels-Modern-Westside-3BR-Bungalow-W-Private-Backyard.h83630896.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
(37 reviews)
"Nice place, great location."
Gordon
CA $171
CA $315 total
includes taxes & fees
Feb 7 - Feb 8
[](https://www.expedia.ca/Roseburg-Hotels-Urban-Boho-Charmer.h72546035.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.
[](https://www.expedia.ca/Roseburg-Hotels-Blue-Downtown-Stay-Eco-Pet-Friendly-Tiny-Twins.h93828604.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)
"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.
CA $266
CA $330 total
includes taxes & fees
Feb 7 - Feb 8
[](https://www.expedia.ca/Roseburg-Hotels-Vrbo-Property.h42977823.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
(91 reviews)
"We had a great stay! The house was amazing, and peaceful. We would definitely stay again. "
Ashley D.
CA $165
CA $290 total
includes taxes & fees
Feb 8 - Feb 9
[](https://www.expedia.ca/Roseburg-Hotels-BrKeasington-House.h61090454.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
(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.
CA $130
CA $248 total
includes taxes & fees
Feb 7 - Feb 8
[](https://www.expedia.ca/Roseburg-Hotels-Red-Tiny-Twins.h95850401.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
(53 reviews)
"It certainly is adorable, well-kept, well-stocked. We would love to stay here again!"
Faith S.
CA $151
CA $248 total
includes taxes & fees
Feb 7 - Feb 8
[](https://www.expedia.ca/Roseburg-Hotels-Adorable-2-Bedroom-1-Bath-House-Pet-Friendly-Nearby-Shopping-And-Hospital.h70497599.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 $150
CA $274 total
includes taxes & fees
Feb 9 - Feb 10
[](https://www.expedia.ca/Roseburg-Hotels-Beulaire.h59613615.Hotel-Information)
### Charming cottage studio in serene environment perfect for a relaxing getaway
[](https://www.expedia.ca/Winston-Hotels-Charming-Cottage-Studio-In-Serene-Environment-Perfect-For-A-Relaxing-Getaway.h119289988.Hotel-Information)
Winston
CA $219
CA $250 total
includes taxes & fees
Mar 9 - Mar 10
[](https://www.expedia.ca/Winston-Hotels-Charming-Cottage-Studio-In-Serene-Environment-Perfect-For-A-Relaxing-Getaway.h119289988.Hotel-Information)
### 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
(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.
CA $204
CA $508 total
includes taxes & fees
Feb 10 - Feb 11
[](https://www.expedia.ca/Winston-Hotels-The-Watusi-Place-A-Modern-Umpqua-Valley-Getaway.h78301309.Hotel-Information)
### Lone Rock Guest House, 20 acres minutes from the North Umpqua River
[](https://www.expedia.ca/Glide-Hotels-Lone-Rock-Guest-House.h121217182.Hotel-Information)
Glide
CA $443
CA $832 total
includes taxes & fees
Feb 20 - Feb 21
[](https://www.expedia.ca/Glide-Hotels-Lone-Rock-Guest-House.h121217182.Hotel-Information)
### Bell Sister Flats
[](https://www.expedia.ca/Roseburg-Hotels-Bell-Sister-Flats.h106623497.Hotel-Information)
Roseburg
CA $406
CA $550 total
includes taxes & fees
Feb 10 - Feb 11
[](https://www.expedia.ca/Roseburg-Hotels-Bell-Sister-Flats.h106623497.Hotel-Information)
### Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
[](https://www.expedia.ca/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.
CA $299
CA $489 total
includes taxes & fees
Feb 11 - Feb 12
[](https://www.expedia.ca/Roseburg-Hotels-Historic-Downtown-Luxurious-Apartment-Only-Steps-Away-From-Local-Restaurants.h38315160.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 $415
CA $480 total
includes taxes & fees
Feb 7 - Feb 8
[](https://www.expedia.ca/Roseburg-Hotels-Private-Bungalow-With-AC-In-Charming-Roseburg.h121040727.Hotel-Information)
### Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
[](https://www.expedia.ca/Roseburg-Hotels-Historic-Downtown-Luxurious-Apartment-Only-Steps-Away-From-Local-Restaurants.h37912072.Hotel-Information)
Roseburg
CA $327
CA $527 total
includes taxes & fees
Feb 8 - Feb 9
[](https://www.expedia.ca/Roseburg-Hotels-Historic-Downtown-Luxurious-Apartment-Only-Steps-Away-From-Local-Restaurants.h37912072.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.
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## Find vacation rentals that suit your style
Aparthotels
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Cabins
[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Oregon%2C+United+States+of+America®ionId=12104&latLong=43.279616%2C-123.353977&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=CABIN)
Apartments
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Cottages
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Villas
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Private vacation homes
[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Oregon%2C+United+States+of+America®ionId=12104&latLong=43.279616%2C-123.353977&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=VACATION_HOME)
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## Top Winchester Hotel Reviews
### Motel 6 Roseburg, OR
10/10 Excellent
"Yes it was perfect"
[](https://expedia.ca/Roseburg-Hotels-Motel-6-Roseburg.h1037746.Hotel-Information)
### Super 8 by Wyndham Roseburg
10/10 Excellent
"Clean room,courteous staff, pleasant stay"
[](https://expedia.ca/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.ca/Roseburg-Hotels-Motel-6-Sutherlin.h425916.Hotel-Information)
### Comfort Inn Roseburg
10/10 Excellent
"Clean room as advertised. Staff is very helpful."
[](https://expedia.ca/Roseburg-Hotels-Comfort-Inn.h17750.Hotel-Information)
### Holiday Inn Express Roseburg by IHG
10/10 Excellent
"Clean room, front desk exceptional..... Room kind of dated.... Good stay... "
[](https://expedia.ca/Roseburg-Hotels-Holiday-Inn-Express-Roseburg.h22705.Hotel-Information)
### Riverfront Inn Roseburg
10/10 Excellent
"Great check-in, the room is super clean with easy parking and a park/river view."
[](https://expedia.ca/Roseburg-Hotels-Riverfront-Inn-Roseburg.h16066.Hotel-Information)
### Best Western Garden Villa Inn
10/10 Excellent
"Yes everything was good. I will definitely stay there again. "
[](https://expedia.ca/Roseburg-Hotels-Best-Western-Garden-Villa-Inn.h7049.Hotel-Information)
### Best Western Plus Hartford Lodge
10/10 Excellent
"Lou was exceptional with check in and quality assurance during the entire stay. He was knowledge and accommodating to our needs. The pool and spa were great working order and offered such a nice space to relax. One of the better Best Western stays! "
[](https://expedia.ca/Roseburg-Hotels-Best-Western-Plus-Hartford-Lodge.h1784775.Hotel-Information)
### SureStay by Best Western Roseburg
10/10 Excellent
" Very comfortable thank you "
[](https://expedia.ca/Roseburg-Hotels-Sleep-Inn-Suites-Roseburg-North-Near-Medical-Center.h539504.Hotel-Information)
## Find out more about Winchester
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 Winchester. 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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- [Vacation Homes in Winchester ](https://expedia.ca/Winchester-Private-Vacation-Homes.d12104-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Winchester ](https://expedia.ca/Winchester-Apartments.d12104-aaApartments.Travel-Guide-Accommodation)
- [Motels in Winchester ](https://expedia.ca/Winchester-Motels.d12104-aaMotels.Travel-Guide-Accommodation)
- [Cottages in Winchester ](https://expedia.ca/Winchester-Cottages.d12104-aaCottages.Travel-Guide-Accommodation)
- [B&B in Winchester ](https://expedia.ca/Winchester-Bed-And-Breakfast.d12104-aaBedAndBreakfast.Travel-Guide-Accommodation)
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- [Farmstay in Winchester ](https://expedia.ca/Winchester-Agritourism.d12104-aaAgritourism.Travel-Guide-Accommodation)
- [Aparthotels in Winchester ](https://expedia.ca/Winchester-Apart-Hotels.d12104-aaApartHotels.Travel-Guide-Accommodation)
## Frequently asked questions
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