Hotels in Winchester

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Check prices for these dates

Next weekend
Aug 7 - Aug 9
In two weeks
Aug 14 - Aug 16

Top 5 hotels in Winchester at a glance

  1. SureStay by Best Western Roseburg — 2.5-star hotel in Roseburg. Guest rating: 8.0/10 — Very Good.
  2. Super 8 by Wyndham Roseburg — 2.5-star hotel in Roseburg. Guest rating: 7.8/10 — Good.
  3. Comfort Inn Roseburg — 2.5-star hotel in Roseburg. Guest rating: 8.4/10 — Very Good.
  4. Best Western Plus Hartford Lodge — 2.5-star hotel in Sutherlin. Guest rating: 8.8/10 — Excellent.
  5. Hampton Inn & Suites Roseburg — 2.5-star hotel in Roseburg. Guest rating: 9.6/10 — Exceptional.

Where to stay in Winchester?

Suite, 2 Queen Beds, Non Smoking (Walk-in Shower;with Sofabed) | Desk, laptop workspace, iron/ironing board, cribs (free)

SureStay by Best Western Roseburg

SureStay by Best Western Roseburg
2.5 star property
Roseburg
8.0 out of 10, Very Good, (1,005 reviews)
The price is $112
$122 total
includes taxes & fees
Aug 9 - Aug 10
SureStay by Best Western Roseburg
Indoor pool

Super 8 by Wyndham Roseburg

Super 8 by Wyndham Roseburg
2.5 star property
Roseburg
7.8 out of 10, Good, (1,009 reviews)
This well-positioned hotel offers an indoor pool and complimentary breakfast, parking, and WiFi. Hike or mountain bike on nearby trails, or visit local attractions like Umpqua Valley Tennis Center and Stewart Park. Travelers consistently praise the quiet setting, helpful staff, and clean rooms.
The price is $81
$88 total
includes taxes & fees
Sep 1 - Sep 2
Super 8 by Wyndham Roseburg
Lobby

Comfort Inn Roseburg

Comfort Inn Roseburg
2.5 star property
Roseburg
8.4 out of 10, Very Good, (1,004 reviews)
This golf-adjacent hotel offers quiet rooms with refrigerators and microwaves. Enjoy the indoor pool and soothing hot tub after exploring nearby Stewart Park. Free breakfast, WiFi, and parking complement the helpful staff and convenient location.
The price is $122
$134 total
includes taxes & fees
Aug 23 - Aug 24
Comfort Inn Roseburg
Exterior

Best Western Plus Hartford Lodge

Best Western Plus Hartford Lodge
2.5 star property
Sutherlin
8.8 out of 10, Excellent, (1,002 reviews)
Just off the highway in Sutherlin, this welcoming hotel offers an indoor pool for year-round swimming and free breakfast to start your day. Explore nearby Umpqua Golf Resort or unwind in rooms with complimentary WiFi after a workout in the fitness center.
The price is $144
$158 total
includes taxes & fees
Aug 13 - Aug 14
Best Western Plus Hartford Lodge
Fireplace

Hampton Inn & Suites Roseburg

Hampton Inn & Suites Roseburg
2.5 star property
Roseburg
9.6 out of 10, Exceptional, (999 reviews)
This comfortable hotel provides free WiFi, self parking, and daily buffet breakfast from 6:00 AM to 10:00 AM. The indoor pool offers year-round relaxation, with Umpqua Valley Tennis Center and Stewart Park just moments away.
The price is $188
$206 total
includes taxes & fees
Aug 22 - Aug 23
Hampton Inn & Suites Roseburg
Exterior

Quality Inn Central Roseburg

Quality Inn Central Roseburg
2.5 star property
Roseburg
7.6 out of 10, Good, (739 reviews)
Just a short drive from Wildlife Safari, this friendly hotel offers complimentary full breakfast and parking. Take a swim in the seasonal outdoor pool after exploring nearby Stewart Park and Umpqua Valley Tennis Center.
The price is $95
$103 total
includes taxes & fees
Aug 9 - Aug 10
Quality Inn Central Roseburg
Exterior

Best Western Garden Villa Inn

Best Western Garden Villa Inn
2.5 star property
Roseburg
8.0 out of 10, Very Good, (1,001 reviews)
Located right off the interstate but surprisingly quiet, this well-maintained Roseburg hotel offers a relaxing hot tub and complimentary breakfast. Nearby Stewart Park and Umpqua Valley Tennis Center provide recreation options, while helpful staff ensure a pleasant stay.
The price is $119
$130 total
includes taxes & fees
Aug 9 - Aug 10
Best Western Garden Villa Inn
BBQ/picnic area

Riverfront Inn Roseburg

Riverfront Inn Roseburg
2.0 star property
Roseburg
8.6 out of 10, Excellent, (1,485 reviews)
The price is $120
$131 total
includes taxes & fees
Sep 1 - Sep 2
Riverfront Inn Roseburg
Property entrance

Motel 6 Sutherlin, OR

Motel 6 Sutherlin, OR
2.0 star property
Sutherlin
7.6 out of 10, Good, (1,001 reviews)
Wake up refreshed at this tranquil motel with free WiFi and parking. Explore adjacent hiking trails or try mountain biking and rafting adventures. Clean rooms and helpful 24-hour staff ensure comfort while Umpqua Golf Resort and Central Park wait just moments away.
The price is $72
$79 total
includes taxes & fees
Aug 16 - Aug 17
Motel 6 Sutherlin, OR
Lobby

The Ranch Motel

The Ranch Motel
2.0 star property
Oakland
9.2 out of 10, Wonderful, (139 reviews)
The price is $109
$111 total
includes taxes & fees
Aug 4 - Aug 5
The Ranch Motel
Lobby sitting area

Rice Hill Inn

Rice Hill Inn
2.0 star property
Oakland
8.0 out of 10, Very Good, (295 reviews)
Wake up in the peaceful Oakland countryside at this welcoming inn. Enjoy free WiFi and parking while exploring nearby hiking and mountain biking trails. MarshAnne Landing attraction awaits just minutes away, and the helpful staff receives consistent praise from fellow travelers.
The price is $79
$80 total
includes taxes & fees
Aug 4 - Aug 5
Rice Hill Inn
Property amenity

The Lodge at Roseburg

The Lodge at Roseburg
3.0 star property
Roseburg
8.8 out of 10, Excellent, (1,000 reviews)
Unwind at this quiet riverside retreat with mountain and city views from lake-facing rooms. Just 15 minutes from Wildlife Safari, enjoy the indoor pool, fitness center, and garden terrace. Stewart Park and Umpqua Valley Tennis Center are located nearby.
The price is $170
$186 total
includes taxes & fees
Aug 13 - Aug 14
The Lodge at Roseburg
Exterior

Holiday Inn Express And Suites Roseburg North By Ihg

Holiday Inn Express And Suites Roseburg North By Ihg
2.5 star property
Roseburg
9.8 out of 10, Exceptional, (56 reviews)
The price is $203
$222 total
includes taxes & fees
Aug 9 - Aug 10
Holiday Inn Express And Suites Roseburg North By Ihg
Exterior

Rosewood Inn and Suites

Rosewood Inn and Suites
2.5 star property
Roseburg
6.4 out of 10, (173 reviews)
Cool off in the outdoor pool at this welcoming motel where free WiFi, parking, and daily breakfast await. Helpful staff earn consistent praise while Umpqua Valley Tennis Center and Stewart Park provide nearby entertainment options.
The price is $70
$77 total
includes taxes & fees
Aug 16 - Aug 17
Rosewood Inn and Suites
Exterior

Howard Johnson by Wyndham Roseburg

Howard Johnson by Wyndham Roseburg
2.0 star property
Roseburg
7.0 out of 10, Good, (841 reviews)
Discover a quiet retreat in Roseburg where helpful staff earn top marks from travelers. This motel offers free WiFi and parking, with a 24-hour front desk for convenience. Stewart Park and Umpqua Valley Tennis Center await just minutes away.
The price is $79
$87 total
includes taxes & fees
Sep 1 - Sep 2
Howard Johnson by Wyndham Roseburg
Basic Double Room | Desk, blackout drapes, iron/ironing board, WiFi (free)

Umpqua Valley Hotel

Umpqua Valley Hotel
2.5 star property
Roseburg
7.2 out of 10, Good, (386 reviews)
Discover comfort in Roseburg at this hotel near Stewart Park and Umpqua Valley Tennis Center. Enjoy a complimentary full breakfast each morning, work out in the 24-hour fitness center, and take advantage of free WiFi and parking during your stay.
The price is $80
$88 total
includes taxes & fees
Sep 1 - Sep 2
Umpqua Valley Hotel
Front of property

Historical John Rast House

Historical John Rast House
3.0 star property
Roseburg
10.0 out of 10, Exceptional, (52 reviews)
Beautifully restored period architecture welcomes you to this authentic getaway in Roseburg. Enjoy hiking trails, kayaking, and rafting nearby while taking advantage of free WiFi and parking. Douglas County Museum and Stewart Park are just minutes away.
The price is $149
$193 total
includes taxes & fees
Aug 4 - Aug 5
Historical John Rast House
Porch

C.H. Bailey House

C.H. Bailey House
2.0 star property
Roseburg
10.0 out of 10, Exceptional, (18 reviews)
The price is $186
$188 total
includes taxes & fees
Aug 4 - Aug 5
C.H. Bailey House
Lobby

Motel 6 Roseburg, OR

Motel 6 Roseburg, OR
2.0 star property
Roseburg
7.8 out of 10, Good, (1,003 reviews)
The price is $78
$86 total
includes taxes & fees
Sep 1 - Sep 2
Motel 6 Roseburg, OR
Deluxe Apartment, City View | Private kitchen

Bell Sister Flats

Bell Sister Flats
2.0 star property
Roseburg
The price is $284
$387 total
includes taxes & fees
Aug 17 - Aug 18
Bell Sister Flats
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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Check out reviews of Winchester hotels guests love

Riverfront Inn Roseburg

Riverfront Inn Roseburg

10/10 Excellent
"Room was modern, clean, well maintained, and bed was comfortable. Location is close to freeway access, but not noisy from freeway traffic. Close to restaurants and river. Only downside is the ample homeless population living under a nearby bridge, however, they were not a bother in any way. Good place. I'd stay again."
STEPHEN 1-night trip
Posted less than an hour ago
Riverfront Inn Roseburg

Frequently asked questions

What accommodations do travelers recommend in Winchester?
Guests like Super 8 by Wyndham Roseburg, Riverfront Inn Roseburg and SureStay by Best Western Roseburg.
Can I book refundable accommodations in Winchester?
If you need the flexibility to change your plans to Winchester, most hotels offer refundable* bookable rates. You can see these properties by searching our site and using the "fully refundable" filter to narrow down the results.
What will the weather in Winchester be like during my trip?
August and July are typically the warmest months in Winchester when the average temp is 64°F. December and February are the coldest months when the average temperature is 41°F. December and March are the months with the most rain.
Why should I book my Winchester accommodation with Hotels.com?
There are lots of reasons to book your Winchester trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.