Title: Winchester Vacation Rentals from $112: Search Short-Term Rentals | Expedia.com
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## Check prices for these dates
In two weeks
[Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=12104&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)
In two months
[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 three months
[May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=12104&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)
In four months
[Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=12104&startDate=2026-06-19&endDate=2026-06-21&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
### Bell Sister Flats
[](https://www.expedia.com/Roseburg-Hotels-Bell-Sister-Flats.h106623497.Hotel-Information)
Roseburg
$378 nightly
$414 total
Mar 5 - Mar 6
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)
"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.
$222 nightly
$243 total
Mar 1 - Mar 2
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Vrbo-Property.h42977823.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)
"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.
$191 nightly
$191 total
Mar 5 - Mar 6
Total with taxes and fees
[](https://www.expedia.com/Myrtle-Creek-Hotels-Charming.h27117565.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)
"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.
$264 nightly
$289 total
Feb 25 - Feb 26
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Modern-Westside-3BR-Bungalow-W-Private-Backyard.h83630896.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 4 - Mar 5
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 25 - Feb 26
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Urban-Boho-Charmer.h72546035.Hotel-Information)
### Lil Cedar Lodge
[](https://www.expedia.com/Umpqua-Hotels-Lil-Cedar-Lodge.h111860176.Hotel-Information)
Roseburg
$111 nightly
$112 total
Feb 25 - Feb 26
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.
$190 nightly
$208 total
Feb 28 - Mar 1
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-BrKeasington-House.h61090454.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 25 - Feb 26
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Private-Bungalow-With-AC-In-Charming-Roseburg.h121040727.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 28 - Mar 1
Total with taxes and fees
[](https://www.expedia.com/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.com/Glide-Hotels-Lone-Rock-Guest-House.h121217182.Hotel-Information)
Glide
$590 nightly
$599 total
Feb 26 - Feb 27
Total with taxes and fees
[](https://www.expedia.com/Glide-Hotels-Lone-Rock-Guest-House.h121217182.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 25 - Feb 26
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)
### 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 25 - Feb 26
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)
### 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.
$155 nightly
$158 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)
### 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 25 - Feb 26
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Beulaire.h59613615.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.
$322 nightly
$353 total
Feb 27 - Feb 28
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Historic-Downtown-Luxurious-Apartment-Only-Steps-Away-From-Local-Restaurants.h38315160.Hotel-Information)
### Grove Stay
[](https://www.expedia.com/Sutherlin-Hotels-Grove-Stay.h122916846.Hotel-Information)
Sutherlin
$221 nightly
$242 total
Feb 25 - Feb 26
Total with taxes and fees
[](https://www.expedia.com/Sutherlin-Hotels-Grove-Stay.h122916846.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.
$312 nightly
$342 total
Feb 28 - Mar 1
Total with taxes and fees
[](https://www.expedia.com/Sutherlin-Hotels-Home-Sweet-Home.h117931389.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
Feb 25 - Feb 26
Total with taxes and fees
[](https://www.expedia.com/Roseburg-Hotels-Red-Tiny-Twins.h95850401.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)
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=2026-03-10&endDate=2026-03-11®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
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=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=CABIN)
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=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=APART_HOTEL)
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=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=VILLA)
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=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=APARTMENT)
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=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=VACATION_HOME)
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=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=COTTAGE)
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## Top Winchester Hotel Reviews
### SureStay by Best Western Roseburg
10/10 Excellent
"The staff was friendly the hotel was clean as was the room. And Lisa prpared a great breakfast. The breakfast was hot and offered waffle or pancake. Bisquits and gravy. Scrambled eggs with ham and vegetables. We felt so welcome diring our stay."
[](https://expedia.com/Roseburg-Hotels-Sleep-Inn-Suites-Roseburg-North-Near-Medical-Center.h539504.Hotel-Information)
### Riverfront Inn Roseburg
10/10 Excellent
"Great location! Clean rooms and helpful staff ! "
[](https://expedia.com/Roseburg-Hotels-Riverfront-Inn-Roseburg.h16066.Hotel-Information)
### Quality Inn Central Roseburg
10/10 Excellent
"Everything here was excellent! So glad I had the privilege of staying here! The staff is amazing! Thank you so much!!!"
[](https://expedia.com/Roseburg-Hotels-Quality-Inn-Central-Roseburg.h663067.Hotel-Information)
### Holiday Inn Express Roseburg by IHG
10/10 Excellent
"Cleanliness, nice breakfast, and the balcony views of the river."
[](https://expedia.com/Roseburg-Hotels-Holiday-Inn-Express-Roseburg.h22705.Hotel-Information)
### Super 8 by Wyndham Roseburg
10/10 Excellent
"Staff was wonderful. Room was clean and we felt safe. Price was right, not a lot of extras but we didn't need them. Great room for the price."
[](https://expedia.com/Roseburg-Hotels-Super-8-By-Wyndham-Roseburg.h159048.Hotel-Information)
### Motel 6 Sutherlin, OR
10/10 Excellent
"Every thing was good "
[](https://expedia.com/Roseburg-Hotels-Motel-6-Sutherlin.h425916.Hotel-Information)
### The Ranch Motel
10/10 Excellent
"My wife and I had a great stay at this motel. The room was clean and well organized. The staff was very friendly and helpful. The rooms are quaint and cozy. Will definitely be starting again if I’m ever back in the area. "
[](https://expedia.com/Oakland-Hotels-The-Ranch-Motel-By-OYO-Oakland-I-5.h90329493.Hotel-Information)
### Comfort Inn Roseburg
10/10 Excellent
"Yes"
[](https://expedia.com/Roseburg-Hotels-Comfort-Inn.h17750.Hotel-Information)
### 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)
## 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?
### What are some of the best vacation rentals that Winchester has to offer?
### What’s there to see and do in Winchester?
### What’s a vacation rental in Winchester like?
### Expedia's Latest Trends
Hotels
- [Best Hotels in Coos Bay](https://expedia.com/Coos-Bay-Hotels.d6041.Travel-Guide-Hotels)
- [Best Hotels in Baker City](https://expedia.com/Baker-City-Hotels.d6367.Travel-Guide-Hotels)
- [Best Hotels in Ashland](https://expedia.com/Ashland-Hotels.d6290.Travel-Guide-Hotels)
- [Best Hotels in Seaside](https://expedia.com/Seaside-Hotels.d6179.Travel-Guide-Hotels)
- [Best Hotels in Newport](https://expedia.com/Newport-Hotels.d9224.Travel-Guide-Hotels)
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- [Best Hotels in Hillsboro](https://expedia.com/Hillsboro-Hotels.d7689.Travel-Guide-Hotels)
- [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)
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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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