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May 12 - May 13
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May 13 - May 14
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Top hotels and accommodation in Winchester

BBQ/picnic area
Riverfront Inn Roseburg
2.0 star property
8.6 out of 10, Excellent, (1079)
"Loved the park setting in front of the river. Loved the convenient proximity to highway. Loved the friendly helpful staff, and the very comfortable bed"
The price is NZ$203
includes taxes & fees
13 May - 14 May
Riverfront Inn Roseburg
Exterior
Super 8 by Wyndham Roseburg
2.5 star property
7.8 out of 10, Good, (1003)
"Liked the hot tub. Clean room. Would have preferred the old Continental breakfast with eggs and more as opposed to just bagels, apples and yogurt. Good staff."
The price is NZ$118
includes taxes & fees
15 May - 16 May
Super 8 by Wyndham Roseburg
Individually decorated, individually furnished, desk, laptop workspace
Sleep Inn & Suites Roseburg North Near Medical Center
2.5 star property
8.0 out of 10, Very good, (1004)
"Nice room. Nice people. No breakfast first two days."
The price is NZ$156
includes taxes & fees
19 May - 20 May
Sleep Inn & Suites Roseburg North Near Medical Center
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Gazebo
Days Inn by Wyndham Roseburg
2.5 star property
6.4 out of 10, (1003)
"I had a decent stay the room and bed were clean and comfortable. Some highway noise but doesn’t bother me. A cheap decent hotel. "
The price is NZ$96
includes taxes & fees
19 May - 20 May
Days Inn by Wyndham Roseburg
Exterior
Best Western Garden Villa Inn
2.5 star property
8.0 out of 10, Very good, (983)
"Amazing stay & nice people in meals area"
The price is NZ$186
includes taxes & fees
19 May - 20 May
Best Western Garden Villa Inn
Lobby
Comfort Inn Roseburg
2.5 star property
8.2 out of 10, Very good, (1007)
"Have stayed here numerous times with and without family, and normally have no issues, but check in was slow as only one person working, and rooms just didn't seem as good our bed was so soft, and our faucet leaked, and the tv had been disabled and only two towels and one hand and wash cloth. Had to ask for more towels for in the pool area. The breakfast was average with hardly any seating. And we were locked out of our rooms at 10am while we were still packing up check out is 11 . All of our ...
The price is NZ$184
includes taxes & fees
28 May - 29 May
Comfort Inn Roseburg
Vending machine
Motel 6 Roseburg, OR
2.0 star property
7.2 out of 10, Good, (914)
"People are so helpful and friendly "
The price is NZ$118
includes taxes & fees
13 May - 14 May
Motel 6 Roseburg, OR
Exterior
Hampton Inn & Suites Roseburg
2.5 star property
9.6 out of 10, Exceptional, (710)
"Great pool for kids. Friendly staff and clean"
The price is NZ$294
includes taxes & fees
27 May - 28 May
Hampton Inn & Suites Roseburg
Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds
Quality Inn Central Roseburg
2.5 star property
7.6 out of 10, Good, (542)
"It’s a clean and comfortable place to stay. "
The price is NZ$153
includes taxes & fees
13 May - 14 May
Quality Inn Central Roseburg
Exterior
Holiday Inn Express Roseburg, an IHG Hotel
2.5 star property
8.8 out of 10, Excellent, (1001)
"beautiful property, view of the river"
The price is NZ$278
includes taxes & fees
30 May - 31 May
Holiday Inn Express Roseburg, an IHG Hotel
Traditional House, 4 Bedrooms, Courtyard View | Living area
Historical John Rast House
3.0 star property
10.0 out of 10, Exceptional, (24)
"The property is amazing! The owners have put so much work in to restoring it, and have so much pride in their work. The couple are so generous in sharing their home! The breakfast was amazing as well!"
The price is NZ$286
includes taxes & fees
13 May - 14 May
Historical John Rast House
Hair dryer, towels, soap, shampoo
Howard Johnson by Wyndham Roseburg
2.0 star property
7.0 out of 10, Good, (747)
"It was fine"
The price is NZ$118
includes taxes & fees
19 May - 20 May
Howard Johnson by Wyndham Roseburg
Suite, 2 Queen Beds, Non Smoking
Baymont by Wyndham Roseburg
2.5 star property
6.8 out of 10, (211)
"Nice place to stay"
The price is NZ$127
includes taxes & fees
19 May - 20 May
Baymont by Wyndham Roseburg
Interior
Cozy Roseburg Home w/ Fire Pit + Gas Grill!
3.5 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!
Exterior
Roseburg Inn
2.0 star property
6.0 out of 10, (33)
"We booked it late. Night the office was open and was helpful "
Roseburg Inn
Property grounds
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
10.0 out of 10, Exceptional, (20)
"We had a very short visit to Roseburg but in that short visit we were treated with white glove service. Thanks so much"
The price is NZ$512
includes taxes & fees
14 May - 15 May
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Exterior
Sweet little Retreat, peacefully/centrally-located. Pet Friendly. 1.5ml off I5
10.0 out of 10, Exceptional, (8)
"Very impressed and happy we found a place to stay when we come to see the grandbabies! Very clean, quiet,,great location and everything we needed was there! Highly recommend!"
Sweet little Retreat, peacefully/centrally-located. Pet Friendly. 1.5ml off I5
Property grounds
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
9.8 out of 10, Exceptional, (16)
"Nice"
The price is NZ$384
includes taxes & fees
25 May - 26 May
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Terrace/patio
The Watusi Place - A Modern Umpqua Valley Getaway
10.0 out of 10, Exceptional, (30)
"We stayed here just one night so we could go to the wildlife safari in the late afternoon. Convenient location. Beautiful well stocked house. Immaculately clean Wildlife Safari was great and very reasonably priced"
The price is NZ$687
includes taxes & fees
13 May - 14 May
The Watusi Place - A Modern Umpqua Valley Getaway
Terrace/patio
Firewater Lodge Cabin Experience
10.0 out of 10, Exceptional, (32)
"An amazingly beautiful cabin in a quiet out of the way area. It has a well stocked kitchen and comfortable hanging out reading on furniture. We did a couple of great hikes and visited two wineries. We are hoping to bring the rest of our family soon."
Firewater Lodge Cabin Experience
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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.

Frequently asked questions

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 100 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 Stewart Park and Melrose 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.