Title: Winchester Vacation Rentals from $112: Search Short-Term Rentals | Expedia.com
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## Check prices for these dates
In two weeks
[Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=12104&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)
In two months
[Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=12104&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 three months
[Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=12104&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)
In four months
[Jul 31 - Aug 2](https://www.expedia.com/Hotel-Search?regionId=12104&startDate=2026-07-31&endDate=2026-08-02&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
### Lil Cedar Lodge
[](https://www.expedia.com/Umpqua-Hotels-Lil-Cedar-Lodge.h111860176.Hotel-Information)
Roseburg
10/10
Exceptional
(1 review)
$111 nightly
$112 total
Apr 8 - Apr 9
Total with taxes and fees
[](https://www.expedia.com/Umpqua-Hotels-Lil-Cedar-Lodge.h111860176.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.
$180 nightly
$180 total
Apr 8 - Apr 9
Total with taxes and fees
[](https://www.expedia.com/A-Restful-Studio-Near-A-Creek-And-Forest.h99919145.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.
$169 nightly
$169 total
Apr 9 - Apr 10
Total with taxes and fees
[](https://www.expedia.com/Myrtle-Creek-Hotels-Charming.h27117565.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
(15 reviews)
"Wonderful environment and very peaceful stay. "
Sarah C.
$155 nightly
$158 total
Apr 8 - Apr 9
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
(39 reviews)
"Nice place, great location."
Gordon
$209 nightly
$229 total
Apr 10 - Apr 11
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Urban-Boho-Charmer.h72546035.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.
$320 nightly
$350 total
Apr 8 - Apr 9
Total with taxes and fees
[](https://www.expedia.com/Sutherlin-Hotels-Home-Sweet-Home.h117931389.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
Apr 8 - Apr 9
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Vrbo-Property.h42977823.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
Apr 8 - Apr 9
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Beulaire.h59613615.Hotel-Information)
### 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
(51 reviews)
"Everything was great! "
Candace L.
$357 nightly
$387 total
Apr 9 - Apr 10
Total with taxes and fees
[](https://www.expedia.com/Winston-Hotels-The-Watusi-Place-A-Modern-Umpqua-Valley-Getaway.h78301309.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
(54 reviews)
"It certainly is adorable, well-kept, well-stocked. We would love to stay here again!"
Faith S.
$211 nightly
$231 total
Apr 8 - Apr 9
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)
###
\~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
(94 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.
$190 nightly
$208 total
May 2 - May 3
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-BrKeasington-House.h61090454.Hotel-Information)
### Downtown Stay at the Blue Tiny Twin
[](https://www.expedia.com/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.
$165 nightly
$181 total
Apr 26 - Apr 27
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Blue-Downtown-Stay-Eco-Pet-Friendly-Tiny-Twins.h93828604.Hotel-Information)
### Modern Mid-Century Retreat with Stylish Amenities & Family-Friendly Comfort
[](https://www.expedia.com/Roseburg-Hotels-Modern-Westside-3BR-Bungalow-W-Private-Backyard.h83630896.Hotel-Information)
Roseburg
9.8/10
Exceptional
(39 reviews)
"As usual this property did not disappoint. Highly recommend! Beds are amazing. "
Barry W.
$313 nightly
$342 total
May 3 - May 4
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Modern-Westside-3BR-Bungalow-W-Private-Backyard.h83630896.Hotel-Information)
### Bell Sister Flats
[](https://www.expedia.com/Roseburg-Hotels-Bell-Sister-Flats.h106623497.Hotel-Information)
Roseburg
$368 nightly
$403 total
Apr 13 - Apr 14
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Bell-Sister-Flats.h106623497.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
(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.
$156 nightly
$170 total
Apr 8 - Apr 9
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Red-Tiny-Twins.h95850401.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
Apr 8 - Apr 9
Total with taxes and fees
[](https://www.expedia.com/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.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.
$331 nightly
$362 total
Apr 8 - Apr 9
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Historic-Downtown-Luxurious-Apartment-Only-Steps-Away-From-Local-Restaurants.h38315160.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.h37912072.Hotel-Information)
Roseburg
$353 nightly
$387 total
Apr 8 - Apr 9
Total with taxes and fees
[](https://www.expedia.com/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.
[View all properties](https://expedia.com/Hotel-Search?startDate=2026-04-21&endDate=2026-04-22®ionId=12104&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)
## Find vacation rentals that suit your style
Cabins
[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Oregon%2C+United+States+of+America®ionId=12104&latLong=43.279616%2C-123.353977&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=CABIN)
Villas
[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Oregon%2C+United+States+of+America®ionId=12104&latLong=43.279616%2C-123.353977&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=VILLA)
Private vacation homes
[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Oregon%2C+United+States+of+America®ionId=12104&latLong=43.279616%2C-123.353977&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=VACATION_HOME)
Aparthotels
[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Oregon%2C+United+States+of+America®ionId=12104&latLong=43.279616%2C-123.353977&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=APART_HOTEL)
Cottages
[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Oregon%2C+United+States+of+America®ionId=12104&latLong=43.279616%2C-123.353977&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=COTTAGE)
Apartments
[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Oregon%2C+United+States+of+America®ionId=12104&latLong=43.279616%2C-123.353977&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=APARTMENT)
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## Top Winchester Hotel Reviews
### Super 8 by Wyndham Roseburg
10/10 Excellent
"Easy access to the Freeway store close by. The staff was great, the pool and hot tub so nice, a great way to end a day of travel. We will definitely stop here on our trip down and back to Yuma next season."
[](https://expedia.com/Roseburg-Hotels-Super-8-By-Wyndham-Roseburg.h159048.Hotel-Information)
### Motel 6 Sutherlin, OR
2/10 Terrible
"Didn't even know a pool existed, and my AC didn't work In my room, it was hot as heck in our room made it a miserable stay and had problems with our TV had to have someone come up and switch out the remote and then the same thing happened got tired of having to ask the front desk to come assist, also my pillows didn't even have pillow cases on them."
[](https://expedia.com/Roseburg-Hotels-Motel-6-Sutherlin.h425916.Hotel-Information)
### SureStay by Best Western Roseburg
10/10 Excellent
"Clean"
[](https://expedia.com/Roseburg-Hotels-Sleep-Inn-Suites-Roseburg-North-Near-Medical-Center.h539504.Hotel-Information)
### Best Western Plus Hartford Lodge
10/10 Excellent
"Staff was incredibly kind and helpful, breakfast was great and the room was clean and comfortable. We loved our stay."
[](https://expedia.com/Roseburg-Hotels-Best-Western-Plus-Hartford-Lodge.h1784775.Hotel-Information)
### Umpqua Valley Hotel
4/10 Poor
"The building was very old "
[](https://expedia.com/Roseburg-Hotels-Umpqua-Valley-Hotel.h24153680.Hotel-Information)
### Riverfront Inn Roseburg
8/10 Good
"The staff were very helpful and friendly "
[](https://expedia.com/Roseburg-Hotels-Riverfront-Inn-Roseburg.h16066.Hotel-Information)
### Comfort Inn Roseburg
8/10 Good
"Clean spacious room, friendly, helpful staff. There were some problems with the coffee, juice and waffle machines. Not sure what was going on there."
[](https://expedia.com/Roseburg-Hotels-Comfort-Inn.h17750.Hotel-Information)
### The Ranch Motel
8/10 Good
"I love the idea of reinvigorating a classic mid century motel. Owners are working hard and I am sure it will be fabulous in future"
[](https://expedia.com/Oakland-Hotels-The-Ranch-Motel-By-OYO-Oakland-I-5.h90329493.Hotel-Information)
### Howard Johnson by Wyndham Roseburg
6/10 Okay
"It’s ok for the price"
[](https://expedia.com/Roseburg-Hotels-Howard-Johnson-By-Wyndham-Roseburg.h6739.Hotel-Information)
## Find out more about Winchester
**Everything you need to know about Winchester 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 Winchester 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 Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.
**Winchester vacation rentals: An excellent choice for every season**
Whenever you want to travel, a warm welcome awaits you in Winchester. 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 Winchester 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 Winchester rentals**
At Expedia, we put the best Winchester 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 Winchester 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 Winchester 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 Winchester. 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 Winchester ](https://expedia.com/Winchester-Private-Vacation-Homes.d12104-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Motels in Winchester ](https://expedia.com/Winchester-Motels.d12104-aaMotels.Travel-Guide-Accommodation)
- [Cottages in Winchester ](https://expedia.com/Winchester-Cottages.d12104-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Winchester ](https://expedia.com/Winchester-Apartments.d12104-aaApartments.Travel-Guide-Accommodation)
- [Cabin Rentals in Winchester ](https://expedia.com/Winchester-Cabins.d12104-aaCabins.Travel-Guide-Accommodation)
- [Farmstay in Winchester ](https://expedia.com/Winchester-Agritourism.d12104-aaAgritourism.Travel-Guide-Accommodation)
- [B&B in Winchester ](https://expedia.com/Winchester-Bed-And-Breakfast.d12104-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Aparthotels in Winchester ](https://expedia.com/Winchester-Apart-Hotels.d12104-aaApartHotels.Travel-Guide-Accommodation)
## Frequently asked questions
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- [Best Hotels in Ontario](https://expedia.com/Ontario-Hotels.d9223.Travel-Guide-Hotels)
- [Best Hotels in Hood River](https://expedia.com/Hood-River-Hotels.d8149.Travel-Guide-Hotels)
- [Best Hotels in Eugene](https://expedia.com/Eugene-Hotels.d602875.Travel-Guide-Hotels)
- [Best Hotels in Cannon Beach](https://expedia.com/Cannon-Beach-Hotels.d86225.Travel-Guide-Hotels)
- [Best Hotels in Klamath Falls](https://expedia.com/Klamath-Falls-Hotels.d6054382.Travel-Guide-Hotels)
- [Best Hotels in Pendleton](https://expedia.com/Pendleton-Hotels.d2757.Travel-Guide-Hotels)
- [Best Hotels in Corvallis](https://expedia.com/Corvallis-Hotels.d6054606.Travel-Guide-Hotels)
- [Best Hotels in Redmond](https://expedia.com/Redmond-Hotels.d2964.Travel-Guide-Hotels)
- [Best Hotels in La Grande](https://expedia.com/La-Grande-Hotels.d8502.Travel-Guide-Hotels)
- [Best Hotels in Astoria](https://expedia.com/Astoria-Hotels.d431.Travel-Guide-Hotels)
- [Best Hotels in Grants Pass](https://expedia.com/Grants-Pass-Hotels.d8032.Travel-Guide-Hotels)
- [Best Hotels in Florence](https://expedia.com/Florence-Hotels.d8100.Travel-Guide-Hotels)
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- [Best Hotels in Medford](https://expedia.com/Medford-Hotels.d602702.Travel-Guide-Hotels)
- [Best Hotels in Bend](https://expedia.com/Bend-Hotels.d6051534.Travel-Guide-Hotels)
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Flights
- [Flights to CVO](https://expedia.com/Cheap-Flights-To-Eugene.d602875.Travel-Guide-Flights)
- [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
- [Car rentals in Eugene](https://expedia.com/Car-Rentals-In-Eugene.d602875.Car-Rental-Guide)
Vacation Rentals
- [Vacation Rental Seaside](https://expedia.com/Seaside-Vacation-Rentals.d6179.Travel-Guide-VacationRentals)
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