Book Cheap Hotels in Winchester

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Tonight
Check prices in Winchester for tonight, Dec 28 - Dec 29
Dec 28 - Dec 29
Tomorrow night
Check prices in Winchester for tomorrow night, Dec 29 - Dec 30
Dec 29 - Dec 30
Next weekend
Check prices in Winchester for next weekend, Jan 2 - Jan 4
Jan 2 - Jan 4

Most frequently booked Winchester hotels

Singing Waters at N. Umpqua

Singing Waters at N. Umpqua

Roseburg North OR
2.45 km from city centre
Get rates
Stay at this vacation home in Roseburg North. Enjoy a beach locale, laundry facilities, and patios. Popular attractions Winchester Dam and Becker Vineyard are located nearby.
Kitchen
Washer
Super 8 by Wyndham Roseburg

Super 8 by Wyndham Roseburg

2.5 out of 5
3200 Nw Aviation Dr I-5 Exit # 127 Roseburg OR
Free cancellation
Reserve now, pay when you stay
3.57 km from city centre
The price is CA $91 per night
CA $91
CA $99 total
Jan 4 - Jan 5, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Umpqua Valley Tennis Center and Stewart Park are located nearby.
Pool
Breakfast included
Motel 6 Roseburg, OR

Motel 6 Roseburg, OR

2 out of 5
3100 Nw Aviation Dr Roseburg OR
Free cancellation
Reserve now, pay when you stay
3.53 km from city centre
The price is CA $76 per night
CA $76
CA $84 total
Dec 29 - Dec 30
includes taxes & fees
Stay at this motel in Roseburg. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Umpqua Valley Tennis Center and Stewart Park are located nearby.
Pet-friendly
Parking included
Comfort Inn Roseburg

Comfort Inn Roseburg

2.5 out of 5
1539 NW Mullholland Drive Roseburg OR
Free cancellation
Reserve now, pay when you stay
5.74 km from city centre
The price is CA $111 per night
CA $111
CA $122 total
Jan 4 - Jan 5, 2026
includes taxes & fees
Book a stay at this golf hotel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Umpqua Valley Tennis Center and Stewart Park are located nearby.
Pool
Hot tub
Riverfront Inn Roseburg

Riverfront Inn Roseburg

2 out of 5
315 W Harvard Ave Roseburg OR
Free cancellation
Reserve now, pay when you stay
7.48 km from city centre
Get rates
Stay at this motel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Stewart Park and Douglas County Museum of History and Natural History are located nearby.
Pool
Breakfast included
Hampton Inn & Suites Roseburg

Hampton Inn & Suites Roseburg

2.5 out of 5
1620 Nw Mulholland Dr Roseburg OR
Free cancellation
Reserve now, pay when you stay
5.63 km from city centre
The price is CA $212 per night
CA $212
CA $232 total
Jan 4 - Jan 5, 2026
includes taxes & fees
Stay at this hotel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Umpqua Valley Tennis Center and Stewart Park are located nearby.
Pool
Breakfast included
Holiday Inn Express Roseburg by IHG

Holiday Inn Express Roseburg by IHG

2.5 out of 5
375 Harvard Blvd Roseburg OR
7.48 km from city centre
The price is CA $144 per night
CA $144
CA $157 total
Jan 2 - Jan 3, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Stewart Park and Umpqua Valley Tennis Center are located nearby.
Pool
Breakfast included
Motel 6 Sutherlin, OR

Motel 6 Sutherlin, OR

2 out of 5
1400 Hospitality Way Sutherlin OR
Free cancellation
Reserve now, pay when you stay
11.74 km from city centre
The price is CA $65 per night
CA $65
CA $72 total
Dec 31 - Jan 1, 2026
includes taxes & fees
Stay at this motel in Sutherlin. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Umpqua Golf Resort and Central Park are located nearby.
Pet-friendly
Parking included
Best Western Garden Villa Inn

Best Western Garden Villa Inn

2.5 out of 5
760 NW Garden Valley Boulevard Roseburg OR
Free cancellation
Reserve now, pay when you stay
5.83 km from city centre
The price is CA $105 per night
CA $105
CA $115 total
Jan 3 - Jan 4, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Umpqua Valley Tennis Center and Stewart Park are located nearby.
Pool
Hot tub
Don't see what you're looking for?
See all available properties in Winchester
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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.

Top hotels in Winchester for Extended Stay

Bell Sister Flats

Bell Sister Flats

620 SE Main St Roseburg OR
The price is CA $353 per night from Jan 1 to Jan 2
CA $353
CA $492 total
Jan 1 - Jan 2, 2026
includes taxes & fees
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.

Winchester hotels essential information

Accommodation
119 hotels
Lowest Price
CA $72
Highest Price
CA $492
Popular hotels
Singing Waters at N. Umpqua, Super 8 by Wyndham Roseburg, Motel 6 Roseburg, OR, Comfort Inn Roseburg, Riverfront Inn Roseburg, Hampton Inn & Suites Roseburg, Holiday Inn Express Roseburg by IHG, Motel 6 Sutherlin, OR, Best Western Garden Villa Inn

Frequently asked questions

What are the top kid-friendly hotels in Winchester?
Family trips are where treasured memories are made, but it's no secret that traveling with young ones can be daunting. These kid-friendly Winchester hotels offer perks designed to keep visitors of all ages relaxed and happy: You're well catered for at Motel 6 Roseburg, OR. It comes with pet-friendly facilities, front desk services and a talent for making families feel at home. Also look into Super 8 by Wyndham Roseburg. It comes with a swimming pool, pet-friendly facilities and plenty of opportunities for precious family time.
Where can I find cheap hotels in Winchester?
At Travelocity you'll find really nice hotels in Winchester at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Winchester rather than in Winchester. We may find you even better rates, too.
How do I find the best Winchester hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Winchester then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Winchester?
The cheapest hotel in Winchester is CA $72 This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Winchester?
There are 119 hotels in Winchester on Travelocity.
What are the best hotels in Winchester?
Winchester has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Winchester for you!
When is the best time to visit Winchester?
If you want the joy of a fun-filled trip in peak season, visit Winchester during March, May and August. If you'd prefer the peace of off-season, book a stay during quieter months, such as October, November and December.
When is the cheapest time to stay in Winchester?
Based on historic data is usually the cheapest month to visit Winchester. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Winchester?
There are multiple hotels in Winchester that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Winchester. We have plenty of kid-friendly hotels in Winchester to choose from on Travelocity!
Why book a hotel in Winchester through Travelocity?
Because we have the top hotels in Winchester! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Winchester on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Winchester hotel reviews by fellow wanderers

Motel 6 Sutherlin, OR

Motel 6 Sutherlin, OR

5 out of 5
Posted 19 hours ago
Travelocity Verified Review
"Staff friendly and helpful "
A verified traveller stayed at Motel 6 Sutherlin, OR
Motel 6 Sutherlin, OR

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