Title: Winchester Vacation Rentals from $112: Search Short-Term Rentals | Expedia.com
[Winchester Travel Guide](https://expedia.com/Winchester.dx12104)[Hotels in Winchester](https://expedia.com/Winchester-Hotels.d12104.Travel-Guide-Hotels)[Flights to Winchester](https://expedia.com/Cheap-Flights-To-Winchester.d12104.Travel-Guide-Flights)[Car Rentals in Winchester](https://expedia.com/Car-Rentals-In-Winchester.d12104.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.com/Winchester.d12104.Destination-Travel-Guides)
## Check prices for these dates
In two weeks
[Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=12104&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=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 three 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 four 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)
## Our top choices for Winchester vacation rentals
### 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)
### Lil Cedar Lodge
[](https://www.expedia.com/Umpqua-Hotels-Lil-Cedar-Lodge.h111860176.Hotel-Information)
Roseburg
$111 nightly
$112 total
Mar 17 - Mar 18
Total with taxes and fees
[](https://www.expedia.com/Umpqua-Hotels-Lil-Cedar-Lodge.h111860176.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 17 - Mar 18
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-BrKeasington-House.h61090454.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 17 - Mar 18
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.
$316 nightly
$346 total
Mar 17 - Mar 18
Total with taxes and fees
[](https://www.expedia.com/Sutherlin-Hotels-Home-Sweet-Home.h117931389.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 17 - Mar 18
Total with taxes and fees
[](https://www.expedia.com/Umpqua-Hotels-Tiny-House-Nestled-Into-The-Forest-On-160-Acre-Playground.h96842207.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 17 - Mar 18
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Beulaire.h59613615.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 17 - Mar 18
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)
### 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 17 - Mar 18
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Red-Tiny-Twins.h95850401.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 17 - Mar 18
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Vrbo-Property.h42977823.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
Mar 21 - Mar 22
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Blue-Downtown-Stay-Eco-Pet-Friendly-Tiny-Twins.h93828604.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 17 - Mar 18
Total with taxes and fees
[](https://www.expedia.com/Myrtle-Creek-Hotels-Charming.h27117565.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
(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 22 - Mar 23
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Bell-Sister-Flats.h106623497.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 17 - Mar 18
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.
$326 nightly
$357 total
Mar 17 - Mar 18
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
$349 nightly
$382 total
Mar 17 - Mar 18
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=2026-03-30&endDate=2026-03-31®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=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&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=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&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=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=APART_HOTEL)
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=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=VACATION_HOME)
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=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=APARTMENT)
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=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=COTTAGE)
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## Top Winchester Hotel Reviews
### Rice Hill Inn
8/10 Good
"Yes"
[](https://expedia.com/Oakland-Hotels-Rice-Hill-Inn.h517554.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)
### 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)
### 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)
### Riverfront Inn Roseburg
10/10 Excellent
"Renovated to modernize, this is a nice older 2 story motel right on the river. And their continental breakfast was much more than expected. More than toast, they provided cereal, bagels, oatmeal packets and hard boiled eggs. Were very satisfied with our stay!"
[](https://expedia.com/Roseburg-Hotels-Riverfront-Inn-Roseburg.h16066.Hotel-Information)
### Rosewood Inn and Suites
2/10 Terrible
"We gave notice 1-1/2 days in advance of cancellation of three days of a six-night reservation. The motel manager wouldn’t give consent to Expedia of the refund so we were ripped off of over $150\. What recourse do we have? The manager was belligerent and our conversation was heated, and he called the police. Refused to cooperate with us. Nothing happened with the police but he got away with our money. This is criminal!"
[](https://expedia.com/Roseburg-Hotels-Rosewood-Inn-And-Suites.h919945.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)
- [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
### Can I find a vacation rental in Winchester?
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- [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)
- [Best Hotels in Bandon](https://expedia.com/Bandon-Hotels.d6328.Travel-Guide-Hotels)
- [Best Hotels in Brookings](https://expedia.com/Brookings-Hotels.d6394.Travel-Guide-Hotels)
- [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)
- [Best Hotels in Roseburg](https://expedia.com/Roseburg-Hotels.d6054633.Travel-Guide-Hotels)
- [Best Hotels in Lincoln City](https://expedia.com/Lincoln-City-Hotels.d8438.Travel-Guide-Hotels)
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)