Find hotels in Winchester, OR from $53

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Winchester hotels

Best Western Plus Hartford Lodge

Best Western Plus Hartford Lodge
2.5 star property
Sutherlin
9.0 out of 10, Wonderful, (1000)
"Friendly people, great location and very clean"
United States
Clarice
$97 nightly
The price is $106
Jan 11 - Jan 12, 2026
Total with taxes and fees
Best Western Plus Hartford Lodge

Umpqua Valley Hotel

Umpqua Valley Hotel
2.5 star property
Roseburg
7.2 out of 10, Good, (345)
"very friendly staff, great breakfast, newly updated clean room"
United States
Kannon
$72 nightly
The price is $79
Dec 26 - Dec 27
Total with taxes and fees
Umpqua Valley Hotel

Comfort Inn Roseburg

Comfort Inn Roseburg
2.5 star property
Roseburg
8.2 out of 10, Very Good, (1002)
"Staff was amazing and room was clean and comfortable "
United States
Danny
$84 nightly
The price is $92
Jan 4 - Jan 5, 2026
Total with taxes and fees
Comfort Inn Roseburg

Quality Inn Central Roseburg

Quality Inn Central Roseburg
2.5 star property
Roseburg
7.6 out of 10, Good, (707)
"It was nice, it had what we needed for our one night stay"
United States
Trisha
$73 nightly
The price is $80
Jan 25 - Jan 26, 2026
Total with taxes and fees
Quality Inn Central Roseburg

SureStay by Best Western Roseburg

SureStay by Best Western Roseburg
2.5 star property
Roseburg
8.0 out of 10, Very Good, (1002)
"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
$79 nightly
The price is $87
Jan 4 - Jan 5, 2026
Total with taxes and fees
SureStay by Best Western Roseburg

Best Western Garden Villa Inn

Best Western Garden Villa Inn
2.5 star property
Roseburg
8.0 out of 10, Very Good, (1002)
"Staff was awesome!"
United States
Keri
$87 nightly
The price is $95
Dec 31 - Jan 1, 2026
Total with taxes and fees
Best Western Garden Villa Inn

Hampton Inn & Suites Roseburg

Hampton Inn & Suites Roseburg
2.5 star property
Roseburg
9.6 out of 10, Exceptional, (963)
"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
$139 nightly
The price is $152
Jan 2 - Jan 3, 2026
Total with taxes and fees
Hampton Inn & Suites Roseburg

Motel 6 Sutherlin, OR

Motel 6 Sutherlin, OR
2.0 star property
Sutherlin
7.6 out of 10, Good, (1000)
"Very pet friendly and great staff."
United States
Nathan
$48 nightly
The price is $53
Dec 28 - Dec 29
Total with taxes and fees
Motel 6 Sutherlin, OR

Howard Johnson by Wyndham Roseburg

Howard Johnson by Wyndham Roseburg
2.0 star property
Roseburg
7.0 out of 10, Good, (822)
"very nice room "
United States
rick
$65 nightly
The price is $71
Dec 26 - Dec 27
Total with taxes and fees
Howard Johnson by Wyndham Roseburg

Rosewood Inn and Suites

Rosewood Inn and Suites
2.5 star property
Roseburg
6.0 out of 10, (125)
"Friendly staff, decent room, all around good experience "
United States
Robert
$61 nightly
The price is $67
Dec 28 - Dec 29
Total with taxes and fees
Rosewood Inn and Suites

Holiday Inn Express Roseburg by IHG

Holiday Inn Express Roseburg by IHG
2.5 star property
Roseburg
8.8 out of 10, Excellent, (1002)
"Comfort,beautiful setting and great breakfasts "
United States
Kristine
$101 nightly
The price is $111
Dec 28 - Dec 29
Total with taxes and fees
Holiday Inn Express Roseburg by IHG

Super 8 by Wyndham Roseburg

Super 8 by Wyndham Roseburg
2.5 star property
Roseburg
7.8 out of 10, Good, (1003)
"Clean room & staff were very nice. "
United States
Evelyn
$66 nightly
The price is $73
Dec 31 - Jan 1, 2026
Total with taxes and fees
Super 8 by Wyndham 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
$90 nightly
The price is $99
Jan 10 - Jan 11, 2026
Total with taxes and fees
Riverfront Inn Roseburg

The Ranch Motel

The Ranch Motel
2.0 star property
Oakland
9.0 out of 10, Wonderful, (79)
"Great stay! "
United States
malyssa
$72 nightly
The price is $74
Jan 6 - Jan 7, 2026
Total with taxes and fees
The Ranch Motel

Rice Hill Inn

Rice Hill Inn
2.0 star property
Oakland
7.8 out of 10, Good, (232)
"Nice clean quiet room with very helpful staff. Would stay again."
United States
Brian
$53 nightly
The price is $54
Dec 26 - Dec 27
Total with taxes and fees
Rice Hill Inn

Safari Inn

Safari Inn
2.0 star property
Winston
7.6 out of 10, Good, (372)
"I enjoyed the friendliness of the staff and the rooms"
United States
Xander
$60 nightly
The price is $65
Dec 26 - Dec 27
Total with taxes and fees
Safari Inn

Quick Stop Motel

Quick Stop Motel
2.0 star property
Myrtle Creek
6.8 out of 10, (135)
"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
$77 nightly
The price is $78
Dec 28 - Dec 29
Total with taxes and fees
Quick Stop Motel

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
$56 nightly
The price is $61
Dec 26 - Dec 27
Total with taxes and fees
Motel 6 Roseburg, OR

Bell Sister Flats

Bell Sister Flats
2.0 star property
Roseburg
$328 nightly
The price is $360
Dec 31 - Jan 1, 2026
Total with taxes and fees
Bell Sister Flats

C.H. Bailey House

C.H. Bailey House
2.0 star property
Roseburg
$258 nightly
The price is $262
Jan 2 - Jan 3, 2026
Total with taxes and fees
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winchester Hotel Reviews

More cheap stays in Winchester

Hotels in Winchester with star-rating

Find out more about Winchester

Top reasons to visit Winchester

  • Outdoor Adventures: Winchester is perfect for hiking, golfing, and exploring scenic parks, making it ideal for adventure seekers.
  • Wine Tasting: The nearby wine country offers delightful tastings, showcasing the region's rich viticulture.
  • Historic Attractions: Visit the Winchester Mystery House and local history museum for a glimpse into the area's unique past.
  • Charming Atmosphere: Enjoy the friendly vibe and welcoming neighborhoods that make Winchester feel like a home away from home.
  • Variety of Accommodations: Choose from cozy motels to family-friendly hotels, catering to all travel needs.

Find great hotels near Winchester

Experience a delightful stay in Winchester, Oregon, where a variety of accommodations await you. From cozy motels to family-friendly hotels, you'll find options tailored to your needs, whether you’re traveling with pets or for business. Discover the best hotels in the area, offering comfortable rooms and convenient amenities for an enjoyable vacation experience.

  • Super 8 by Wyndham Roseburg: Located a mere 2 miles from Winchester, Super 8 by Wyndham Roseburg is an ideal choice for pet-friendly travelers seeking a comfortable and business-oriented stay. This hotel features essential amenities such as a 24-hour business center and meeting rooms, making it suitable for those on work trips or conferences. Pets are welcome, with policies that accommodate dogs, ensuring that your furry friends can join you on your travels. With a friendly atmosphere and convenient services, this hotel provides a practical base for exploring the region.
  • Comfort Inn Roseburg: Situated 4 miles from Winchester, Comfort Inn Roseburg caters to families, business travelers, and golf enthusiasts alike. This hotel offers a robust suite of business amenities, including a 24-hour business center and a location within a business district. Golf lovers can take advantage of nearby courses, while families will appreciate child-friendly features such as free cribs and a well-equipped first aid kit. With its blend of leisure and practicality, Comfort Inn ensures a memorable stay for all types of travelers.
  • Motel 6 Roseburg, OR: Just 2 miles away from Winchester, Motel 6 Roseburg, OR is a budget-friendly option perfect for those traveling with pets. This motel allows pets at no extra charge, making it an excellent choice for pet owners. While offering straightforward accommodations, the property maintains a welcoming atmosphere for both you and your four-legged companions. With its affordable rates and convenient location, Motel 6 provides a hassle-free lodging experience for cost-conscious travelers.

Where to stay near Winchester

Winchester, Oregon, offers a refreshing outdoor experience perfect for adventure seekers and families alike. Explore the nearby wine country and enjoy scenic excursions while soaking in the friendly atmosphere of this charming city. With its budget-friendly options and welcoming neighborhoods, Winchester serves as an ideal base for discovering the natural beauty and vibrant culture of the region. Whether you're hiking, tasting local wines, or simply relaxing, Winchester promises an unforgettable vacation experience.

  • Roseburg: Located a mere 4 miles from Winchester, Roseburg is a vibrant city that attracts visitors year-round, with peak travel during the summer months. Known for its stunning outdoor scenery and adventurous spirit, Roseburg offers a variety of recreational activities. Visitors can enjoy nearby national and state parks, as well as picturesque lakes. Whether you're looking to hike, fish, or simply take in the views, Roseburg is a gateway to natural beauty and relaxation.
  • Roseburg North: Just 3 miles from Winchester, Roseburg North shares the charm of its neighboring city while boasting its own unique attractions. Also popular among outdoor enthusiasts, this area provides ample opportunities for adventure. The proximity to lakes and national parks makes it an ideal spot for those looking to explore nature. Visitors can engage in educational activities and visit local resorts, ensuring a well-rounded travel experience that highlights the region's rich landscape.
  • Wilbur: A quaint village located 3 miles from Winchester, Wilbur is perfect for travelers seeking a peaceful getaway. While it sees a slight increase in visitors during the spring and summer months, its allure remains constant throughout the year. Known for its outdoor adventures and proximity to stunning lakes and national parks, Wilbur is a great destination for hiking and exploring. With a relaxed atmosphere, this village provides a charming stop for anyone looking to immerse themselves in the area's natural beauty.

Things to do near Winchester

Winchester, Oregon, is a fantastic destination for outdoor enthusiasts seeking adventure and beautiful scenery. Visitors can enjoy a variety of activities, including golfing, wine tastings, and relaxing at local resorts. The town also features recreational areas perfect for outdoor fun and a movie theater for entertainment. With its charming atmosphere and numerous attractions, Winchester promises an enjoyable vacation experience.

Shopping

In Winchester, you can explore local shops for unique gifts and souvenirs. If you're up for a drive, head to the nearby Valley River Center in Eugene for a larger selection of retail stores and dining options, making it a great day trip for shopping enthusiasts.

Recreation

Umpqua Golf Resort offers a scenic golfing experience with vibrant outdoor vibes, perfect for relaxing and enjoying nature. Herbert's Pond Park is a tranquil spot for wellness and relaxation, featuring beautiful landscapes. Brunch Bar Wayside combines leisure and wellness, providing a delightful place to unwind and savor delicious food.

Adventure

Explore the Umpqua Valley Tennis Center, located 4 miles from Winchester, where you can enjoy exciting matches and improve your tennis skills amidst a vibrant atmosphere. The center offers a fantastic environment for both beginners and experienced players looking for a fun challenge.

Nightlife

Experience the vibrant nightlife in Winchester by visiting the River's Edge Restaurant for stunning views and tasty cocktails. For a fun, relaxed atmosphere, check out the local brewpub offering a variety of craft beers and live music to enjoy with friends.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Winchester

To save money on your trip to Winchester, Oregon, consider visiting between December and February when hotel prices are lower, especially on Mondays. Utilize Expedia to compare prices, filter by budget, and explore eco-friendly accommodations. Bundling your hotel, flights, and activities can unlock additional savings, and joining the One Key membership may offer exclusive discounts and cash back for future stays. Look for hotel deals and booking tips to ensure a secure and cost-effective travel experience.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Winchester are December to February, where the prices are slightly lower. This is in comparison to June to August, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Winchester is Monday. The most expensive day to stay in Winchester is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia's search tool to refine your preferences, such as your budget, desired location, and hotel type. For instance, selecting the Eco-certified option will showcase sustainable and eco-friendly accommodations currently available. To find the best prices and deals, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay in Winchester with your flights and activities through an Expedia package deal.
  • Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions near Winchester

Winchester, Oregon, is perfect for outdoor enthusiasts and those seeking scenic adventures. Popular attractions include urban parks, a dam, and the history museum, making it ideal for family outings or romantic getaways. Don't miss the Winchester Mystery House, the local museum, and the stunning Winchester Cathedral for a taste of history and culture. Enjoy exploring the best attractions this charming city has to offer.

  • Winchester Dam: Located just 0.4 miles from Winchester, this scenic dam offers breathtaking views and a peaceful atmosphere. It's an ideal spot for photography, picnics, or simply enjoying nature's beauty.
  • Stewart Park: About 4 miles away, Stewart Park is a vibrant urban park perfect for families. With its expansive green spaces, playgrounds, and walking trails, it's a great place to unwind and enjoy outdoor activities.
  • Discovery Garden: Also 4 miles from Winchester, this botanical garden is a romantic escape filled with diverse plant species. Stroll through beautifully landscaped paths, making it an excellent destination for families and couples alike.

Best time to go to Winchester

The best time to visit Winchester is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are slightly high and weather is sunny with no rain. December is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January40.6°F (4.8°C)Light RainMostly CloudyAverageSlightly Low
February41.0°F (5.0°C)Light RainMostly CloudyAverageSlightly Low
March43.7°F (6.5°C)Light RainMostly CloudyAverageAverage
April48.0°F (8.9°C)Light RainMostly CloudyAverageAverage
May54.3°F (12.4°C)Light RainMostly SunnyAverageAverage
June60.1°F (15.6°C)No RainMostly SunnySlightly HighSlightly High
July66.4°F (19.1°C)No RainMostly SunnySlightly HighSlightly High
August66.9°F (19.4°C)No RainSunnySlightly HighSlightly High
September61.9°F (16.6°C)No RainMostly SunnyAverageAverage
October53.2°F (11.8°C)Light RainMostly SunnySlightly LowAverage
November44.4°F (6.9°C)Light RainMostly CloudySlightly LowAverage
December39.0°F (3.9°C)Light RainMostly CloudySlightly LowSlightly Low

The nearest major airports for your trip to Winchester

Traveling to Winchester, Oregon, is convenient with two major airports nearby. Eugene Airport (EUG) is situated 58 miles away, with excellent hotel options such as Graduate by Hilton Eugene and Inn at the 5th, both rated 4 stars and located 8 miles from the airport. Valley River Inn, a 3.5-star hotel, is only 7 miles from EUG. Alternatively, North Bend Airport (OTH) is 46 miles from Winchester, featuring hotels like Red Lion Hotel Coos Bay and Global INN, both 3 miles away, and Quality Inn & Suites at Coos Bay, just 0.8 miles from the airport. Each hotel offers easy access to their respective airports.

Frequently asked questions

When is the best time to go to Winchester?
The most popular time to visit Winchester is in the late spring and early summer, particularly June. During this month, temperatures typically range from the mid-60s to low 70s Fahrenheit, providing a pleasant climate for exploring the city's historic sites and beautiful gardens. With extended daylight hours, you'll have ample opportunity to enjoy outdoor activities, such as strolling through the picturesque Winchester Cathedral grounds or wandering along the River Itchen.

As you delve into your travel plans, be aware that the peak season runs from June to August. This is when Winchester enjoys a vibrant atmosphere, filled with visitors eager to experience its rich history and local culture. Events such as the popular Winchester Hat Fair in July and the annual Winchester Science Festival in June add to the lively backdrop, making it an ideal time for those who appreciate engaging community experiences.

For travelers seeking a quieter experience, consider visiting in September. This month often sees fewer crowds, allowing you to explore the city at a more leisurely pace while still benefiting from mild weather. You can relish the stunning autumn colors in the surrounding countryside, making it a superb time for scenic walks or bike rides.
Can I cancel my hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Winchester hotel for you.
How can I save on a Winchester hotel booking with Expedia?
With Expedia, you earn OneKeyCash™* on eligible Winchester hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a Winchester hotel?
Prices for hotels in Winchester often vary, but you can find a great deal from $53 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

Explore a world of travel with Expedia