Title: Winchester Vacation Rentals from $112: Search Short-Term Rentals | Expedia.com
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## Check prices for these dates
In two weeks
[Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=12104&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
[Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=12104&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
[May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=12104&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
[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)
## Our top choices for Winchester vacation rentals
### Lil Cedar Lodge
[](https://www.expedia.com/Umpqua-Hotels-Lil-Cedar-Lodge.h111860176.Hotel-Information)
Roseburg
$111 nightly
$112 total
Feb 15 - Feb 16
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
(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.
$180 nightly
$180 total
Feb 15 - Feb 16
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
(42 reviews)
"Enjoyed our stay!"
Dana M.
$165 nightly
$165 total
Feb 23 - Feb 24
Total with taxes and fees
[](https://www.expedia.com/A-Restful-Studio-Near-A-Creek-And-Forest.h99919145.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
(37 reviews)
"Nice place, great location."
Gordon
$206 nightly
$226 total
Feb 15 - Feb 16
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Urban-Boho-Charmer.h72546035.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)
"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.
$218 nightly
$239 total
Feb 14 - Feb 15
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Vrbo-Property.h42977823.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.
$165 nightly
$181 total
Feb 15 - Feb 16
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)
### 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
(48 reviews)
"Home was well stocked and was very accessible to our winery we belong to. "
Amy W.
$333 nightly
$361 total
Feb 15 - Feb 16
Total with taxes and fees
[](https://www.expedia.com/Winston-Hotels-The-Watusi-Place-A-Modern-Umpqua-Valley-Getaway.h78301309.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.
$310 nightly
$339 total
Feb 19 - Feb 20
Total with taxes and fees
[](https://www.expedia.com/Sutherlin-Hotels-Home-Sweet-Home.h117931389.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
Feb 15 - Feb 16
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Beulaire.h59613615.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
(91 reviews)
"We had a great stay! The house was amazing, and peaceful. We would definitely stay again. "
Ashley D.
$194 nightly
$212 total
Feb 28 - Mar 1
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
(13 reviews)
"Wonderful environment and very peaceful stay. "
Sarah C.
$169 nightly
$172 total
Feb 28 - Mar 1
Total with taxes and fees
[](https://www.expedia.com/Umpqua-Hotels-Tiny-House-Nestled-Into-The-Forest-On-160-Acre-Playground.h96842207.Hotel-Information)
### Charming cottage studio in serene environment perfect for a relaxing getaway
[](https://www.expedia.com/Winston-Hotels-Charming-Cottage-Studio-In-Serene-Environment-Perfect-For-A-Relaxing-Getaway.h119289988.Hotel-Information)
Winston
$180 nightly
$183 total
Feb 16 - Feb 17
Total with taxes and fees
[](https://www.expedia.com/Winston-Hotels-Charming-Cottage-Studio-In-Serene-Environment-Perfect-For-A-Relaxing-Getaway.h119289988.Hotel-Information)
### Bell Sister Flats
[](https://www.expedia.com/Roseburg-Hotels-Bell-Sister-Flats.h106623497.Hotel-Information)
Roseburg
$375 nightly
$411 total
Feb 20 - Feb 21
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
(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.
$165 nightly
$181 total
Feb 15 - Feb 16
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Red-Tiny-Twins.h95850401.Hotel-Information)
### Lone Rock Guest House, 20 acres minutes from the North Umpqua River
[](https://www.expedia.com/Glide-Hotels-Lone-Rock-Guest-House.h121217182.Hotel-Information)
Glide
$590 nightly
$599 total
Feb 20 - Feb 21
Total with taxes and fees
[](https://www.expedia.com/Glide-Hotels-Lone-Rock-Guest-House.h121217182.Hotel-Information)
### Grove Stay
[](https://www.expedia.com/Sutherlin-Hotels-Grove-Stay.h122916846.Hotel-Information)
Sutherlin
$234 nightly
$256 total
Feb 14 - Feb 15
Total with taxes and fees
[](https://www.expedia.com/Sutherlin-Hotels-Grove-Stay.h122916846.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.
$320 nightly
$350 total
Feb 16 - Feb 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)
### 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
Feb 15 - Feb 16
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.h37912072.Hotel-Information)
Roseburg
$349 nightly
$382 total
Feb 16 - Feb 17
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=2026-02-27&endDate=2026-02-28®ionId=12104&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)
##
The Annual Vacation Sale
Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
[Book now](https://expedia.com/deals?rfrr=VR_SPRING_PROMO_12104)
## Find vacation rentals that suit your style
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=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&lodging=VACATION_HOME)
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=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&lodging=VILLA)
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=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&lodging=APART_HOTEL)
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=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&lodging=APARTMENT)
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=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&lodging=CABIN)
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=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&lodging=COTTAGE)
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## Top Winchester Hotel Reviews
### Best Western Plus Hartford Lodge
10/10 Excellent
"Cleanest room I’ve ever been in. "
[](https://expedia.com/Roseburg-Hotels-Best-Western-Plus-Hartford-Lodge.h1784775.Hotel-Information)
### Holiday Inn Express Roseburg by IHG
10/10 Excellent
"Best hotel in Roseburg, and great staff!"
[](https://expedia.com/Roseburg-Hotels-Holiday-Inn-Express-Roseburg.h22705.Hotel-Information)
### Motel 6 Sutherlin, OR
10/10 Excellent
"all great - night clerk very helpful"
[](https://expedia.com/Roseburg-Hotels-Motel-6-Sutherlin.h425916.Hotel-Information)
### Riverfront Inn Roseburg
10/10 Excellent
"The room was clean and the staff were very friendly."
[](https://expedia.com/Roseburg-Hotels-Riverfront-Inn-Roseburg.h16066.Hotel-Information)
### Hampton Inn & Suites Roseburg
10/10 Excellent
"I really enjoyed staying the night at this hotel. Everyone at the front desk was so sweet and kind. I am senior solo traveler, and I felt very safe on my own in this hotel. The parking lot is safe. The breakfast was really good. Lots of choices from hot food to cold cereal."
[](https://expedia.com/Roseburg-Hotels-Hampton-Inn-Suites-Roseburg.h22270751.Hotel-Information)
### Umpqua Valley Hotel
10/10 Excellent
"The late night staff was very welcoming and the room was nice and clean."
[](https://expedia.com/Roseburg-Hotels-Umpqua-Valley-Hotel.h24153680.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.com/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.com/Roseburg-Hotels-Comfort-Inn.h17750.Hotel-Information)
### Motel 6 Roseburg, OR
10/10 Excellent
"Yes it was perfect"
[](https://expedia.com/Roseburg-Hotels-Motel-6-Roseburg.h1037746.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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- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)
- [Vacation Homes in Winchester ](https://expedia.com/Winchester-Private-Vacation-Homes.d12104-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Winchester ](https://expedia.com/Winchester-Apartments.d12104-aaApartments.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)
- [Lodges in Winchester ](https://expedia.com/Winchester-Lodges.d12104-aaLodges.Travel-Guide-Accommodation)
- [B&B in Winchester ](https://expedia.com/Winchester-Bed-And-Breakfast.d12104-aaBedAndBreakfast.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)
- [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)
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- [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)
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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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