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Top hotels and accommodation in Winchester

Riverfront Inn Roseburg

2.0 star property
8.6 out of 10, Excellent, (1238)
"Ann, the night clerk, demonstrated some of highest qualities in Customer Service. Her keen awareness of the propriety and well being of its guests reflected a warm and kind attitude after we traveled all day. I highly recommend this hotel for ALL travelers."
The price is AU$164
includes taxes & fees
24 Dec - 25 Dec
Riverfront Inn Roseburg

Comfort Inn Roseburg

2.5 star property
8.2 out of 10, Very good, (1007)
"Nice overnight stay and I would definitely stay here on future trips. "
The price is AU$156
includes taxes & fees
24 Dec - 25 Dec
Comfort Inn Roseburg

Super 8 by Wyndham Roseburg

2.5 star property
7.6 out of 10, Good, (1004)
"Best Super 8 we have ever stayed at!"
The price is AU$119
includes taxes & fees
29 Dec - 30 Dec
Super 8 by Wyndham Roseburg

Best Western Garden Villa Inn

2.5 star property
8.0 out of 10, Very good, (1002)
"Great staff. Good breakfast (not great). Room location was next to vending machines (not good if you have to sleep early)."
The price is AU$134
includes taxes & fees
28 Dec - 29 Dec
Best Western Garden Villa Inn

Hampton Inn & Suites Roseburg

2.5 star property
9.6 out of 10, Exceptional, (819)
"Great room with remote control curtains, loved the comp breakfast. "
The price is AU$252
includes taxes & fees
29 Dec - 30 Dec
Hampton Inn & Suites Roseburg

Sleep Inn & Suites Roseburg North Near Medical Center

2.5 star property
8.0 out of 10, Very good, (1005)
"Super clean, good for a family stay. Lots of shopping and dining options within 5min."
The price is AU$127
includes taxes & fees
5 Jan - 6 Jan 2025
Sleep Inn & Suites Roseburg North Near Medical Center

Holiday Inn Express Roseburg, an IHG Hotel

2.5 star property
8.8 out of 10, Excellent, (1002)
"This hotel is perfect for traveling with a pet! Very accommodating and welcoming. The man at the front desk was very kind and helpful. The added pet fee is nominal. Expedia will reject my review if I state the cost. They also do not tell you to expect the added fee for a pet when making a reservation. Go directly to the hotel website to find out, before you book. The hotel is a bit aged, as far as decor goes. It is comfortable, though, and our room had a lovely view of the river. We slept quite...
The price is AU$228
includes taxes & fees
27 Dec - 28 Dec
Holiday Inn Express Roseburg, an IHG Hotel

Days Inn by Wyndham Roseburg

2.5 star property
6.2 out of 10, (1002)
"really hard to find/get to"
The price is AU$95
includes taxes & fees
29 Dec - 30 Dec
Days Inn by Wyndham Roseburg

Motel 6 Roseburg, OR

2.0 star property
7.4 out of 10, Good, (1004)
"It’s a no frills chain, so: no frills, but it is very nice for that category, and the staff are friendly, helpful and professional."
The price is AU$100
includes taxes & fees
12 Jan - 13 Jan 2025
Motel 6 Roseburg, OR

Baymont by Wyndham Roseburg

2.5 star property
7.0 out of 10, Good, (264)
"Friendly staff. Pleasant stay. Updated room."
The price is AU$118
includes taxes & fees
29 Dec - 30 Dec
Baymont by Wyndham Roseburg

Quality Inn Central Roseburg

2.5 star property
7.6 out of 10, Good, (607)
"Decent place with clean rooms. Nothing fancy but good value for money"
The price is AU$119
includes taxes & fees
4 Jan - 5 Jan 2025
Quality Inn Central Roseburg

Howard Johnson by Wyndham Roseburg

2.0 star property
7.0 out of 10, Good, (792)
"Good hotel price was fair. "
The price is AU$105
includes taxes & fees
29 Dec - 30 Dec
Howard Johnson by Wyndham Roseburg

Tiny House nestled into the Forest on 160 acre Playground.

8.8 out of 10, Excellent, (3)
"We had an amazing time here it was so quite and peaceful and the host were amazing we will be going back"
The price is AU$278
includes taxes & fees
24 Dec - 25 Dec
Tiny House nestled into the Forest on 160 acre Playground.

Bell Sister Flats

2.0 star property
The price is AU$860
includes taxes & fees
24 Dec - 25 Dec
Bell Sister Flats

Roseburg Inn

2.0 star property
6.0 out of 10, (33)
"We booked it late. Night the office was open and was helpful "
The price is AU$131
includes taxes & fees
24 Dec - 25 Dec
Roseburg Inn

Luxury, Full Service Bed and Breakfast - you are the only guest in our home!

10.0 out of 10, Exceptional, (21)
"Excellent experience! We were passing through and wanted a cozy experience from multiple hotel stays. Our hosts were outstanding and so friendly, attentive to every little detail to make us feel welcomed and comfortable. An outstanding bed and breakfast experience!"
The price is AU$359
includes taxes & fees
3 Jan - 4 Jan 2025
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!

Cozy Roseburg Home w/ Fire Pit + Gas Grill!

3.0 star property
9.0 out of 10, Wonderful, (2)
"Attractive tiny house, well equipped, peaceful neighborhood, convenient to town. Bedroom is a bit small, but living area and bath (with shower and washer/dryer) are good sized. Helpful owner suggested Brix local restaurant we really liked too. Nearby Upper Umpquah waterfalls, hiking, river rafting made a nice vacation."
Cozy Roseburg Home w/ Fire Pit + Gas Grill!

Firewater Lodge Cabin Experience

10.0 out of 10, Exceptional, (45)
"We loved everything about our stay here!! Wonderful communication with our host, clean, and quiet were some of our first impressions! Check-in and checkout were simple and everything I could have thought of as a question is answered for me before I think of it. Open and comfortable living area made for a great movie night. We enjoyed playing in the creek and sitting by the fire pit! The kitchen was fully stocked, so appreciated! The beds provided plenty of space for all of us and everyone...
Firewater Lodge Cabin Experience

Monroe River House. Jacuzzi. Private Beach. Prime Location. Family Friendly.

10.0 out of 10, Exceptional, (6)
"The Monroe River House in Roseburg, OR was the perfect home for us. The master bedroom was spacious, and the bed was super comfortable. Having an additional BR and bathroom was a bonus, too. The house and kitchen were well-stocked and had everything we needed and more - like plastic bags to keep food in, etc. The yard was huge, and we spent a few afternoons hanging out at the little beach on the river at the bottom of the property. The area is beautiful with lots of local wineries nearby. We...
The price is AU$763
includes taxes & fees
14 Jan - 15 Jan 2025
Monroe River House. Jacuzzi. Private Beach. Prime Location. Family Friendly.

The Watusi Place - A Modern Umpqua Valley Getaway

10.0 out of 10, Exceptional, (34)
"We had a great stay and home was just what was advertised. There were so many personal touches and the owner was great to deal with. There was a problem with the A/C before we arrived which was quickly relayed to us by owner and they had it fixed just after our arrival. We will definitely be back next time we are in town. "
The price is AU$591
includes taxes & fees
3 Jan - 4 Jan 2025
The Watusi Place - A Modern Umpqua Valley Getaway
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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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 Comfort Inn Roseburg and Sleep Inn & Suites Roseburg North Near Medical Center. See all available top hotels, or vacation rentals in Winchester.

What are some of the best holiday rentals that Winchester has to offer?

Indigo Collective - Modern Home: This holiday home rental outside Winchester has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. 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 are some hotels with pools in Winchester?

Super 8 by Wyndham Roseburg: Features free breakfast, a pool and free self-parking. Best Western Plus Hartford Lodge and Comfort Inn are two additional hotels that feature an on-site pool. View all hotels with pools in Winchester.

What's it like to stay in Winchester?

Visitors can enjoy all that Winchester has to offer, including its restaurants. There are 98 hotels and other accommodation options in the surrounding area. 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 Melrose Vineyards and Reustle Prayer Rock 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.