Title: Winchester Holiday Homes from £120: Search Holiday Homes in Winchester | Expedia.co.uk
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## Check prices for these dates
In two weeks
[20 Mar - 22 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=12104&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)
In two months
[1 May - 3 May](https://www.expedia.co.uk/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 three months
[29 May - 31 May](https://www.expedia.co.uk/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)
In four months
[26 Jun - 28 Jun](https://www.expedia.co.uk/Hotel-Search?regionId=12104&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)
## Our top choices for Winchester holiday homes
### A Restful Studio Near a Creek and Forest - Pets
[](https://www.expedia.co.uk/A-Restful-Studio-Near-A-Creek-And-Forest.h99919145.Hotel-Information)
Roseburg
10/10
Exceptional
(43 reviews)
"Enjoyed our stay!"
Dana M.
£126
includes taxes & fees
4 Mar - 5 Mar
[](https://www.expedia.co.uk/A-Restful-Studio-Near-A-Creek-And-Forest.h99919145.Hotel-Information)
###
\~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
[](https://www.expedia.co.uk/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.
£157
includes taxes & fees
3 Mar - 4 Mar
[](https://www.expedia.co.uk/Roseburg-Hotels-BrKeasington-House.h61090454.Hotel-Information)
### Tiny House nestled into the Forest on 160 acre Playground.
[](https://www.expedia.co.uk/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.
£120
includes taxes & fees
3 Mar - 4 Mar
[](https://www.expedia.co.uk/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.co.uk/Roseburg-Hotels-Urban-Boho-Charmer.h72546035.Hotel-Information)
Roseburg
9.6/10
Exceptional
(38 reviews)
"Nice place, great location."
Gordon
£170
includes taxes & fees
3 Mar - 4 Mar
[](https://www.expedia.co.uk/Roseburg-Hotels-Urban-Boho-Charmer.h72546035.Hotel-Information)
### The Watusi Place - A Modern Umpqua Valley Getaway
[](https://www.expedia.co.uk/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.
£267
includes taxes & fees
3 Mar - 4 Mar
[](https://www.expedia.co.uk/Winston-Hotels-The-Watusi-Place-A-Modern-Umpqua-Valley-Getaway.h78301309.Hotel-Information)
### Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
[](https://www.expedia.co.uk/Roseburg-Hotels-Luxury.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.
£179
includes taxes & fees
3 Mar - 4 Mar
[](https://www.expedia.co.uk/Roseburg-Hotels-Luxury.h42977823.Hotel-Information)
### Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
[](https://www.expedia.co.uk/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.
£137
includes taxes & fees
3 Mar - 4 Mar
[](https://www.expedia.co.uk/Roseburg-Hotels-Adorable-2-Bedroom-1-Bath-House-Pet-Friendly-Nearby-Shopping-And-Hospital.h70497599.Hotel-Information)
### Home Sweet Home
[](https://www.expedia.co.uk/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.
£256
includes taxes & fees
3 Mar - 4 Mar
[](https://www.expedia.co.uk/Sutherlin-Hotels-Home-Sweet-Home.h117931389.Hotel-Information)
### Stunning Views\~
Beulaire, a MCM Hillside Retreat Suite.
Beautiful Views\~
[](https://www.expedia.co.uk/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.
£149
includes taxes & fees
3 Mar - 4 Mar
[](https://www.expedia.co.uk/Roseburg-Hotels-Beulaire.h59613615.Hotel-Information)
### Grove Stay
[](https://www.expedia.co.uk/Sutherlin-Hotels-Grove-Stay.h122916846.Hotel-Information)
Sutherlin
£182
includes taxes & fees
3 Mar - 4 Mar
[](https://www.expedia.co.uk/Sutherlin-Hotels-Grove-Stay.h122916846.Hotel-Information)
### Downtown Stay at the Blue Tiny Twin
[](https://www.expedia.co.uk/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.
£137
includes taxes & fees
21 Mar - 22 Mar
[](https://www.expedia.co.uk/Roseburg-Hotels-Blue-Downtown-Stay-Eco-Pet-Friendly-Tiny-Twins.h93828604.Hotel-Information)
### Downtown Stay at the Red Tiny Twin!
[](https://www.expedia.co.uk/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.
£129
includes taxes & fees
3 Mar - 4 Mar
[](https://www.expedia.co.uk/Roseburg-Hotels-Red-Tiny-Twins.h95850401.Hotel-Information)
### Private bungalow with AC in charming Roseburg
[](https://www.expedia.co.uk/Roseburg-Hotels-Private-Bungalow-With-AC-In-Charming-Roseburg.h121040727.Hotel-Information)
Roseburg
£258
includes taxes & fees
3 Mar - 4 Mar
[](https://www.expedia.co.uk/Roseburg-Hotels-Private-Bungalow-With-AC-In-Charming-Roseburg.h121040727.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.co.uk/Hotel-Search?startDate=2026-03-16&endDate=2026-03-17®ionId=12104&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)
##
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[Book now](https://expedia.co.uk/cheap-deals?rfrr=AA_SPRING_PROMO_12104)
## Find holiday rentals that suit your style
Aparthotels
[](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Oregon%2C+United+States+of+America®ionId=12104&latLong=43.279616%2C-123.353977&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=APART_HOTEL)
Apartments
[](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Oregon%2C+United+States+of+America®ionId=12104&latLong=43.279616%2C-123.353977&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=APARTMENT)
Villas
[](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Oregon%2C+United+States+of+America®ionId=12104&latLong=43.279616%2C-123.353977&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=VILLA)
Private holiday homes
[](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Oregon%2C+United+States+of+America®ionId=12104&latLong=43.279616%2C-123.353977&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=VACATION_HOME)
Cottages
[](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Oregon%2C+United+States+of+America®ionId=12104&latLong=43.279616%2C-123.353977&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=COTTAGE)
Cabins
[](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Oregon%2C+United+States+of+America®ionId=12104&latLong=43.279616%2C-123.353977&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=CABIN)
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## Top Winchester Hotel Reviews
### Motel 6 Roseburg, OR
10/10 Excellent
"Everything perfect"
[](https://expedia.co.uk/Roseburg-Hotels-Motel-6-Roseburg.h1037746.Hotel-Information)
### Motel 6 Sutherlin, OR
10/10 Excellent
"Outstanding "
[](https://expedia.co.uk/Roseburg-Hotels-Motel-6-Sutherlin.h425916.Hotel-Information)
### Best Western Plus Hartford Lodge
10/10 Excellent
"Custom cooked breakfast. Best hotel breakfast I have ever had almost without exception. I expect to have $25 for this at a restaurant "
[](https://expedia.co.uk/Roseburg-Hotels-Best-Western-Plus-Hartford-Lodge.h1784775.Hotel-Information)
### SureStay by Best Western Roseburg
10/10 Excellent
"Nice staff, clean room, nice breakfast. Not fancy but perfectly suitable for a quick stay."
[](https://expedia.co.uk/Roseburg-Hotels-Sleep-Inn-Suites-Roseburg-North-Near-Medical-Center.h539504.Hotel-Information)
### Comfort Inn Roseburg
10/10 Excellent
"Everything was great"
[](https://expedia.co.uk/Roseburg-Hotels-Comfort-Inn.h17750.Hotel-Information)
### Riverfront Inn Roseburg
10/10 Excellent
"Great location! Clean rooms and helpful staff ! "
[](https://expedia.co.uk/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.co.uk/Roseburg-Hotels-Quality-Inn-Central-Roseburg.h663067.Hotel-Information)
### The Lodge at Roseburg
10/10 Excellent
"Cleanliness, nice breakfast, and the balcony views of the river."
[](https://expedia.co.uk/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.co.uk/Roseburg-Hotels-Super-8-By-Wyndham-Roseburg.h159048.Hotel-Information)
## Find out more about Winchester
## Winchester Holiday Homes information
| Number of reviews | 352 |
| ----------------- | ---------------- |
| Accommodation | 48 Holiday Homes |
| Lowest Price | £120 |
| Highest Price | £267 |
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