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June 2026

July 2026

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Our top choices for Winchester bed & breakfast

C.H. Bailey House

Roseburg

David

includes taxes & fees

3 June - 4 June

Historical John Rast House

Roseburg

Barbara

includes taxes & fees

20 May - 21 May

1 Bedroom Queen Suite- Historic Lodge on the North Umpqua River

Glide

includes taxes & fees

24 May - 25 May

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Top Winchester Hotel Reviews

Super 8 by Wyndham Roseburg

10/10 Excellent

"Clean and convenient. Would recommend."

Riverfront Inn Roseburg

8/10 Good

"My husband and I stayed at Riverfront Inn in Roseburg in May of 2026. The room was clean, decently updated and had everything we needed for our short stay. The staff were very friendly and accommodating. They knew we were from out of town and they even offered suggestions on places to eat. My only complaint is that the mattress was too firm, so I didn't sleep well but that seems to be the trend for motels and hotels these days."

Howard Johnson by Wyndham Roseburg

6/10 Okay

"Check in staff was professional and friendly. My room was clean, however the tub area needs attention, not sure if it was mold or something else on the lower wall and areas around the caulking. It would be nice if a grab bar was available in the tub/shower area. All in all, it is a hair away from being a dilapidated building. I believe breakfast was to be provided, but that didn’t come to fruition, per a sign on the office door the lobby didn’t open until 10A when I dropped my key in the designated box. I’m not sure, but it seems that available rooms may be provided for the houseless with dogs, I.e. German shepherd size. A couple with such a dog was in the room above mine. Although it was not barking I could hear the dog running back running back and forth as if chasing a ball for almost an hour. Other rooms had guests with dogs also. Yes I’m aware that pets were welcomed, just odd that so many guests had big dogs. "

Best Western Plus Hartford Lodge

10/10 Excellent

"This hotel was a nice surprise. The room was clean and spacious. Lisa at the front desk was very friendly and helpful. The breakfast included made-to-order eggs by a cook that has been there for years. There are few restaurants in the town, but Dakota's (pizza) was very good. Otherwise, you might want to stop for dinner before arriving in Sutherlin."

Umpqua Valley Hotel

6/10 Okay

"Staff was great. Room was clean enough but worn as was the entire motel. Easy parking but homeless across the street made me think twice about leaving anythingin the car- there were no problems. Breakfast was horrible.Scrambled eggs tasteless, suasages overcooked, dry, and tough, waffle had a funny taste, apples mediocre, oranges looking bad. I wanted to give this a better rating but just couldn't."

Find out more about Winchester

Winchester B&B information

Number of reviews	49
Accommodation	2 B&B
Lowest Price	AU$236
Highest Price	AU$307

Frequently asked questions

Searching for B&Bs in Winchester?

If you want to find a place to stay with fewer rooms than a hotel and a more personalised environment, a B&B might be just the right fit for your trip to Winchester. When you want to explore some of the destination's attractions, North Umpqua River is worth a visit.

Why would you choose B&Bs instead of traditional hotels?

Every B&B has its own unique feel — whether it's a garden for guests to admire or a sunlit breakfast nook to enjoy your morning cup of coffee, the small details are what make bed and breakfasts a fun place to get away.

What are the top B&Bs in Winchester?

Here are some B&Bs in the surrounding area: C.H. Bailey House: 5 rooms. 9.7 mi (15.6 km) from the heart of Winchester. Enjoy the free full breakfast and Hot tub. Historical John Rast House: 3 rooms. 4.7 mi (7.5 km) from the city centre. 1 Bedroom Queen Suite- Historic Lodge on the North Umpqua River: 17.1 mi (27.6 km) from the city centre.

What's the best time of year to book my B&B in Winchester?

When you're dreaming of a escape to Winchester, make sure that you take the year-round temperatures into account. 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.

What is there to do in Winchester?

If you want to see some popular attractions in Winchester, you might enjoy a visit to North Umpqua River. You might also consider a trip to sites such as Stewart Park or Melrose Vineyards if you have time to see more of the area.

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winchester bed & breakfast

C.H. Bailey House

Historical John Rast House

1 Bedroom Queen Suite- Historic Lodge on the North Umpqua River

Top Winchester Hotel Reviews

Super 8 by Wyndham Roseburg

SureStay by Best Western Roseburg

Riverfront Inn Roseburg

Howard Johnson by Wyndham Roseburg

Quality Inn Central Roseburg

Best Western Plus Hartford Lodge

Hampton Inn & Suites Roseburg

Best Western Garden Villa Inn

Umpqua Valley Hotel

Find out more about Winchester

Winchester B&B information

Frequently asked questions

Explore a world of travel with Expedia