Find hotels in Winchester, OR from ฿1,634

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24 Dec - 25 Dec
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25 Dec - 26 Dec
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26 Dec - 28 Dec
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2 Jan - 4 Jan

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Our top choices for Winchester hotels

Exterior
Best Western Plus Hartford Lodge

Best Western Plus Hartford Lodge

Best Western Plus Hartford Lodge
2.5 star property
Sutherlin
9.0 out of 10, Wonderful, (1000)
Located near Umpqua Golf Resort and Central Park, this hotel offers convenient amenities including an indoor pool for morning swims. Enjoy free WiFi and parking during your stay, with a fitness centre to maintain your workout routine.
"Friendly people, great location and very clean"
United States
Clarice
The price is ฿3,011
฿3,297 total
includes taxes & fees
11 Jan - 12 Jan 2026
Best Western Plus Hartford Lodge
Basic Double Room | Desk, blackout curtains, iron/ironing board, free WiFi
Umpqua Valley Hotel

Umpqua Valley Hotel

Umpqua Valley Hotel
2.5 star property
Roseburg
7.2 out of 10, Good, (345)
Step into modern comfort at this Roseburg retreat near Stewart Park. The 24-hour fitness centre keeps workouts on schedule while free perks include daily full breakfast, WiFi and parking for effortless adventures.
"very friendly staff, great breakfast, newly updated clean room"
United States
Kannon
The price is ฿2,240
฿2,452 total
includes taxes & fees
25 Dec - 26 Dec
Umpqua Valley Hotel
Lobby
Comfort Inn Roseburg

Comfort Inn Roseburg

Comfort Inn Roseburg
2.5 star property
Roseburg
8.2 out of 10, Very good, (1002)
Travellers praise the quiet atmosphere and convenient Roseburg location of this hotel. Enjoy the indoor pool, hot tub, and 24-hour fitness centre after exploring nearby Stewart Park. Rooms include refrigerators and microwaves, plus free breakfast, WiFi, and parking.
"Staff was amazing and room was clean and comfortable "
United States
Danny
The price is ฿2,606
฿2,853 total
includes taxes & fees
4 Jan - 5 Jan 2026
Comfort Inn Roseburg
Exterior
Quality Inn Central Roseburg

Quality Inn Central Roseburg

Quality Inn Central Roseburg
2.5 star property
Roseburg
7.6 out of 10, Good, (707)
Located within a 15-minute drive of Wildlife Safari, this Quality Inn offers a refreshing seasonal outdoor pool and complimentary full breakfast served daily. Free parking adds convenience while the helpful staff ensures a pleasant stay near Umpqua Valley Tennis Centre and Stewart Park.
"It was nice, it had what we needed for our one night stay"
United States
Trisha
The price is ฿2,278
฿2,494 total
includes taxes & fees
22 Jan - 23 Jan 2026
Quality Inn Central Roseburg
Suite, 2 Queen Beds, Non Smoking (Walk-in Shower;with Sofabed) | Individually decorated, individually furnished, desk, laptop workspace
SureStay by Best Western Roseburg

SureStay by Best Western Roseburg

SureStay by Best Western Roseburg
2.5 star property
Roseburg
8.0 out of 10, Very good, (1003)
"Very friendly desk staff, room is nice, clean and comfortable. Haven driven past on the freeway will be staying again in the future "
United States
Ray
The price is ฿2,459
฿2,692 total
includes taxes & fees
4 Jan - 5 Jan 2026
SureStay by Best Western Roseburg
Exterior
Best Western Garden Villa Inn

Best Western Garden Villa Inn

Best Western Garden Villa Inn
2.5 star property
Roseburg
8.0 out of 10, Very good, (1002)
Surprisingly peaceful despite interstate proximity, this Roseburg hotel offers relaxing hot tub soaks after exploring nearby Stewart Park. Clean rooms, helpful staff, and perks like free breakfast, WiFi, and parking complete your stay.
"Staff was awesome!"
United States
Keri
The price is ฿2,697
฿2,953 total
includes taxes & fees
31 Dec - 1 Jan 2026
Best Western Garden Villa Inn
Fireplace
Hampton Inn & Suites Roseburg

Hampton Inn & Suites Roseburg

Hampton Inn & Suites Roseburg
2.5 star property
Roseburg
9.6 out of 10, Exceptional, (963)
Located in Roseburg, this hotel offers a refreshing indoor pool and complimentary daily buffet breakfast served from 6:00 AM. Guests appreciate the helpful staff and convenient amenities including free WiFi and parking, with easy access to Stewart Park and Umpqua Valley Tennis Centre.
"It was a great stay. The staff was extemely helpful and the special Santa moment really made the kids excited. Thank you everyone."
United States
Mary
The price is ฿4,311
฿4,720 total
includes taxes & fees
2 Jan - 3 Jan 2026
Hampton Inn & Suites Roseburg
Desk, free WiFi, bed sheets
Motel 6 Sutherlin, OR

Motel 6 Sutherlin, OR

Motel 6 Sutherlin, OR
2.0 star property
Sutherlin
7.6 out of 10, Good, (1002)
Tranquil motel offering free WiFi and parking, with easy access to Umpqua Golf Resort and Central Park. Travellers praise the helpful staff and clean rooms, plus outdoor adventures like hiking, biking, and rafting await just minutes away.
"Very pet friendly and great staff."
United States
Nathan
The price is ฿1,484
฿1,634 total
includes taxes & fees
28 Dec - 29 Dec
Motel 6 Sutherlin, OR
Exterior
Howard Johnson by Wyndham Roseburg

Howard Johnson by Wyndham Roseburg

Howard Johnson by Wyndham Roseburg
2.0 star property
Roseburg
7.0 out of 10, Good, (822)
Find solitude at this tranquil motel offering free WiFi and parking. Located near Stewart Park and Umpqua Valley Tennis Centre, guests consistently praise the attentive staff. The on-site breakfast lobby provides a convenient start to your day.
"very nice room "
United States
rick
The price is ฿2,022
฿2,214 total
includes taxes & fees
25 Dec - 26 Dec
Howard Johnson by Wyndham Roseburg
Exterior
Rosewood Inn and Suites

Rosewood Inn and Suites

Rosewood Inn and Suites
2.5 star property
Roseburg
6.0 out of 10, (125)
Located near Umpqua Valley Tennis Centre and Stewart Park, this motel offers free breakfast, WiFi and parking. Take a swim in the outdoor pool after exploring local attractions. Previous guests consistently praise the exceptionally helpful staff.
"Friendly staff, decent room, all around good experience "
United States
Robert
The price is ฿2,022
฿2,214 total
includes taxes & fees
25 Dec - 26 Dec
Rosewood Inn and Suites
Free daily buffet breakfast
Holiday Inn Express Roseburg by IHG

Holiday Inn Express Roseburg by IHG

Holiday Inn Express Roseburg by IHG
2.5 star property
Roseburg
8.8 out of 10, Excellent, (1001)
Nestled in a beautiful spot with river and mountain views, this Roseburg hotel offers an indoor pool for morning swims and a fitness centre. Quiet rooms provide tranquility despite highway proximity, with Stewart Park just minutes away.
"Comfort,beautiful setting and great breakfasts "
United States
Kristine
The price is ฿3,142
฿3,440 total
includes taxes & fees
28 Dec - 29 Dec
Holiday Inn Express Roseburg by IHG
Indoor pool
Super 8 by Wyndham Roseburg

Super 8 by Wyndham Roseburg

Super 8 by Wyndham Roseburg
2.5 star property
Roseburg
7.8 out of 10, Good, (1003)
Enjoy the indoor pool after a day of hiking or mountain biking nearby. This Roseburg hotel offers free breakfast, WiFi, and parking. Clean rooms and helpful staff ensure a comfortable stay, with Stewart Park and Umpqua Valley Tennis Centre just minutes away.
"Clean room & staff were very nice. "
United States
Evelyn
The price is ฿2,062
฿2,258 total
includes taxes & fees
31 Dec - 1 Jan 2026
Super 8 by Wyndham Roseburg
BBQ/picnic Area
Riverfront Inn Roseburg

Riverfront Inn Roseburg

Riverfront Inn Roseburg
2.0 star property
Roseburg
8.6 out of 10, Excellent, (1429)
"Check in was super easy and the room was clean and comfortable. "
Canada
Melanie
Riverfront Inn Roseburg
Lobby
The Ranch Motel

The Ranch Motel

The Ranch Motel
2.0 star property
Oakland
9.0 out of 10, Wonderful, (79)
"Great stay! "
United States
malyssa
The price is ฿2,703
฿2,744 total
includes taxes & fees
25 Dec - 26 Dec
The Ranch Motel
Exterior
Rice Hill Inn

Rice Hill Inn

Rice Hill Inn
2.0 star property
Oakland
7.8 out of 10, Good, (232)
This inviting motel offers complementary WiFi and parking near Oakland's natural beauty. Outdoor enthusiasts can explore nearby hiking and mountain biking trails, with MarshAnne Landing just a short drive away.
"Nice clean quiet room with very helpful staff. Would stay again."
United States
Brian
The price is ฿1,652
฿1,676 total
includes taxes & fees
31 Dec - 1 Jan 2026
Rice Hill Inn
Property entrance
Safari Inn

Safari Inn

Safari Inn
2.0 star property
Winston
7.6 out of 10, Good, (372)
Located minutes from Wildlife Safari and South Umpqua River, this Winston motel offers complimentary WiFi and parking. Guests appreciate the helpful staff and 24-hour front desk service, making it a convenient base for exploring local attractions.
"I enjoyed the friendliness of the staff and the rooms"
United States
Xander
The price is ฿1,866
฿2,025 total
includes taxes & fees
26 Dec - 27 Dec
Safari Inn
Property grounds
Quick Stop Motel

Quick Stop Motel

Quick Stop Motel
2.0 star property
Myrtle Creek
6.8 out of 10, (135)
Located near South Umpqua River, this welcoming motel offers free WiFi and parking with daily housekeeping service. Explore nearby Pyrenees Vineyard & Cellars for local wine tasting during your comfortable stay.
"It was super quiet and for that - a nice retreat. Amenities are far away so guests will need to have everything with, otherwise a drive for such could be 10+ miles. No frills at all, but quiet and affordable"
United States
Aaron
The price is ฿2,152
฿2,184 total
includes taxes & fees
25 Dec - 26 Dec
Quick Stop Motel
Front of property
Motel 6 Roseburg, OR

Motel 6 Roseburg, OR

Motel 6 Roseburg, OR
2.0 star property
Roseburg
7.6 out of 10, Good, (1002)
"Room was clean and staff were also very nice."
United States
Santanu
The price is ฿1,731
฿1,906 total
includes taxes & fees
25 Dec - 26 Dec
Motel 6 Roseburg, OR
Deluxe Apartment, City View | Private kitchen
Bell Sister Flats

Bell Sister Flats

Bell Sister Flats
2.0 star property
Roseburg
Bell Sister Flats offers comfortable accommodation with free WiFi near city centre Roseburg. Just minutes from Douglas County Museum and Stewart Park, this aparthotel provides a convenient base for exploring local history and natural attractions.
The price is ฿8,914
฿12,145 total
includes taxes & fees
25 Dec - 26 Dec
Bell Sister Flats
Porch
C.H. Bailey House

C.H. Bailey House

C.H. Bailey House
2.0 star property
Roseburg
The price is ฿8,025
฿8,146 total
includes taxes & fees
2 Jan - 3 Jan 2026
C.H. Bailey House
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.
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Top Winchester Hotel Reviews

Rosewood Inn and Suites

Rosewood Inn and Suites

10/10 Excellent
"Great!"
Brittney 1-night trip
Posted 10 days ago
Rosewood Inn and Suites
Umpqua Valley Hotel

Umpqua Valley Hotel

10/10 Excellent
"Room is clean, nice staff, with a light breakfast "
Qian 1-night trip
Posted 1 month ago
Umpqua Valley Hotel

More cheap stays in Winchester

Motel 6 Roseburg, OR

Motel 6 Roseburg, OR

3100 Nw Aviation Dr Roseburg OR
The price is ฿1,731 per night from 25 Dec to 26 Dec
฿1,731
฿1,906 total
25 Dec - 26 Dec
includes taxes & fees
7.4/10 Good! (1,002 reviews)

Frequently asked questions

Where is the best place for a stay in Winchester?
Riverfront Inn Roseburg, located 4.6 mi (7.5 km) from the heart of Winchester, is a top choice for your stay, based on our traveller data. Other good choices for your stay in the area are Super 8 by Wyndham Roseburg and Motel 6 Roseburg, OR. See all available top hotels, or vacation rentals in Winchester.
What are some of the best holiday rentals that Winchester has to offer?
River Vista Vacation Homes: This holiday home rental outside Winchester is located on a river, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a coffee maker. See all vacation rentals in Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes! Most hotel bookings are fully refundable provided that you cancel before the hotel's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If you have a reservation that's non-refundable, you might be able to cancel it and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
What's it like to stay in Winchester?
Visitors can enjoy all that Winchester has to offer, including its restaurants. In Winchester, there are 2 hotels and other accommodation options to choose from. Find out more about Winchester.
What are the top places to visit in Winchester?
A favourite place to visit is North Umpqua River. You'll also find Stewart Park and Melrose Vineyards in the area. Take a look at what more there is to see and do in Expedia's Winchester guide.
What's the seasonal weather like in Winchester?
The hottest months are usually August and July, with an average temperature of 18°C, while the coldest months are December and February, with an average of 5°C. Average annual precipitation for Winchester is 1255 mm.