Hotels in Winchester

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight
Mar 23 - Mar 24
Tomorrow
Mar 24 - Mar 25
This weekend
Mar 27 - Mar 29
Next weekend
Apr 3 - Apr 5

Where to stay in Winchester?

Lobby sitting area
Rice Hill Inn
Rice Hill Inn
2.0 star property
Oakland
7.8 out of 10, Good, (239 reviews)
  • cleanliness
    Rustic inn near hiking trails and MarshAnne Landing with complimentary perks.
The price is $59
$60 total
includes taxes & fees
Mar 24 - Mar 25
Rice Hill Inn
Lobby
The Ranch Motel
The Ranch Motel
2.0 star property
Oakland
9.0 out of 10, Wonderful, (84 reviews)
The price is $77
$78 total
includes taxes & fees
Mar 24 - Mar 25
The Ranch Motel
Exterior
Best Western Plus Hartford Lodge
Best Western Plus Hartford Lodge
2.5 star property
Sutherlin
9.0 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Wake to friendly service and spacious comfort at this Sutherlin retreat.
The price is $121
$133 total
includes taxes & fees
Mar 29 - Mar 30
Best Western Plus Hartford Lodge
Property entrance
Motel 6 Sutherlin, OR
Motel 6 Sutherlin, OR
2.0 star property
Sutherlin
7.6 out of 10, Good, (1,001 reviews)
  • cleanliness
    Peaceful oasis in Sutherlin with hiking trails and mountain biking nearby.
The price is $54
$60 total
includes taxes & fees
Mar 24 - Mar 25
Motel 6 Sutherlin, OR
Porch
C.H. Bailey House
C.H. Bailey House
2.0 star property
Roseburg
10.0 out of 10, Exceptional, (3 reviews)
The price is $194
$197 total
includes taxes & fees
Mar 24 - Mar 25
C.H. Bailey House
Indoor pool
Super 8 by Wyndham Roseburg
Super 8 by Wyndham Roseburg
2.5 star property
Roseburg
8.0 out of 10, Very Good, (1,002 reviews)
  • cleanliness
    Experience a peaceful stay with easy access to Roseburg's outdoor adventures.
The price is $65
$71 total
includes taxes & fees
Mar 24 - Mar 25
Super 8 by Wyndham Roseburg
Exterior
Howard Johnson by Wyndham Roseburg
Howard Johnson by Wyndham Roseburg
2.0 star property
Roseburg
7.0 out of 10, Good, (824 reviews)
  • cleanliness
    A peaceful stay near Stewart Park with helpful staff and free amenities.
The price is $59
$64 total
includes taxes & fees
Mar 24 - Mar 25
Howard Johnson by Wyndham 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
2.5 star property
Roseburg
8.0 out of 10, Very Good, (1,003 reviews)
The price is $88
$97 total
includes taxes & fees
Mar 29 - Mar 30
SureStay by Best Western Roseburg
Front of property
Historical John Rast House
Historical John Rast House
3.0 star property
Roseburg
10.0 out of 10, Exceptional, (49 reviews)
  • cleanliness
    Experience genuine 19th-century charm at this historic B&B near Douglas County Museum.
The price is $149
$193 total
includes taxes & fees
Mar 24 - Mar 25
Historical John Rast House
Deluxe Apartment, City View | Private kitchen
Bell Sister Flats
Bell Sister Flats
2.0 star property
Roseburg
The price is $315
$422 total
includes taxes & fees
Mar 25 - Mar 26
Bell Sister Flats
Lobby
Comfort Inn Roseburg
Comfort Inn Roseburg
2.5 star property
Roseburg
8.2 out of 10, Very Good, (1,001 reviews)
  • cleanliness
    Stay comfortably in Roseburg with golf, pool, and hot tub for relaxation after play.
The price is $95
$103 total
includes taxes & fees
Mar 29 - Mar 30
Comfort Inn Roseburg
Fireplace
Hampton Inn & Suites Roseburg
Hampton Inn & Suites Roseburg
2.5 star property
Roseburg
9.6 out of 10, Exceptional, (983 reviews)
  • cleanliness
    Enjoy an indoor pool and complimentary breakfast near Stewart Park in Roseburg.
The price is $162
$178 total
includes taxes & fees
Apr 5 - Apr 6
Hampton Inn & Suites Roseburg
Exterior
Quality Inn Central Roseburg
Quality Inn Central Roseburg
2.5 star property
Roseburg
7.6 out of 10, Good, (711 reviews)
  • cleanliness
    Unwind at this Roseburg hotel with a refreshing outdoor pool and daily breakfast.
The price is $76
$83 total
includes taxes & fees
Mar 29 - Mar 30
Quality Inn Central Roseburg
Lobby
Motel 6 Roseburg, OR
Motel 6 Roseburg, OR
2.0 star property
Roseburg
7.6 out of 10, Good, (1,006 reviews)
The price is $54
$60 total
includes taxes & fees
Mar 25 - Mar 26
Motel 6 Roseburg, OR
Pool
Holiday Inn Express And Suites Roseburg North By Ihg
Holiday Inn Express And Suites Roseburg North By Ihg
2.5 star property
Roseburg
10.0 out of 10, Exceptional, (4 reviews)
The price is $161
$176 total
includes taxes & fees
Apr 5 - Apr 6
Holiday Inn Express And Suites Roseburg North By Ihg
Exterior
Rosewood Inn and Suites
Rosewood Inn and Suites
2.5 star property
Roseburg
6.0 out of 10, (128 reviews)
  • cleanliness
    Enjoy a refreshing stay in Roseburg with free amenities and nearby attractions.
The price is $55
$60 total
includes taxes & fees
Mar 24 - Mar 25
Rosewood Inn and Suites
Basic Double Room | Desk, blackout drapes, iron/ironing board, free WiFi
Umpqua Valley Hotel
Umpqua Valley Hotel
2.5 star property
Roseburg
7.2 out of 10, Good, (349 reviews)
  • cleanliness
    A welcoming stay close to Stewart Park with fitness and free full breakfast daily.
The price is $80
$88 total
includes taxes & fees
Mar 24 - Mar 25
Umpqua Valley Hotel
BBQ/picnic area
Riverfront Inn Roseburg
Riverfront Inn Roseburg
2.0 star property
Roseburg
8.6 out of 10, Excellent, (1,439 reviews)
The price is $99
$108 total
includes taxes & fees
Mar 24 - Mar 25
Riverfront Inn Roseburg
Exterior
The Lodge at Roseburg
The Lodge at Roseburg
2.5 star property
Roseburg
8.8 out of 10, Excellent, (1,003 reviews)
  • cleanliness
    Riverside escape with quick access to Stewart Park and a refreshing indoor pool.
The price is $134
$147 total
includes taxes & fees
Mar 27 - Mar 28
The Lodge at Roseburg
Exterior
Best Western Garden Villa Inn
Best Western Garden Villa Inn
2.5 star property
Roseburg
8.0 out of 10, Very Good, (1,002 reviews)
  • cleanliness
    Experience serene stays just off the interstate, with a hot tub and free breakfast.
The price is $100
$110 total
includes taxes & fees
Mar 29 - Mar 30
Best Western Garden Villa Inn
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

Check out reviews of Winchester hotels guests love

Best Western Garden Villa Inn

Best Western Garden Villa Inn

2/10 Terrible
"Place was a dump"
Jessica 2-night trip
Posted 9 hours ago
Best Western Garden Villa Inn

Frequently asked questions

What accommodations do travelers recommend in Winchester?
Guests like The Lodge at 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.