Ashland’s Winchester Inn tops USA Today list of 10 best bed-and-breakfasts

The Winchester Inn on Second Street in Ashland. Winchester Inn photo
August 25, 2024

Hosting reporter writing article on Ashland pays off for historic 2nd Street inn 

By Cameron Aalto, Ashland.news

USA Today lists Ashland’s Winchester Inn at the top of a list of the nation’s 10 best bed-and-breakfasts in an article published Aug. 14.

“We had a travel writer come and write an article about Ashland, and that got us on the radar for the USA Today’s expert judges,” explained second-generation Winchester owner Drew Gibbs. “That got us on the top-20 list, and then from there we ended up in the number-one spot.” 

The article includes a description of the bed-and-breakfast, saying, “Step back in time when you stay in one of the 21 well-appointed guest rooms and suites located in the main house, Heritage House, Carriage House, or one of the two cottages.” It also highlighted the inn’s on-site restaurant, Alchemy, which cellars more than 650 wines, half from local Oregon wineries.

The entry to Winchester Inn off Second Street in Ashland. Andrea Johnson Photography

‘If this brings extra people to the valley to visit, then that’s a win for us, and that’s a win for everybody.’

More info
To learn more about the Winchester Inn, visit its website by clicking here.

To read the National Park Service National Register of Historic Places listing on what was originally the Fordyce Roper House, click here.

The award came to the Inn on its 40th year of business. Gibbs said, “it’s pretty cool to receive something like that on the 40th year that you’ve been open.”

Asked whether the award would open more doors for the business, Gibbs explained that, while he would like to have more guests, “we only have so many rooms … so unfortunately I can’t fit as many as I’d like.” That said, he shared that the inn’s main goal “has always just been to spotlight Ashland and the Rogue Valley in particular as an amazing place to stay. …

“The reality is, is that if this brings extra people to the valley to visit, then that’s a win for us, and that’s a win for everybody. … I would say it’s our dedication to service and hospitality and I really do take huge pride in how amazing our staff is. As much as I would love to be able to say, ‘yes, I can do it all,’ we’ve got all of these amazing people helping us enact the level of quality and service that we want to see, and they take huge pride in that.”

The Winchester offers a full two course seasonal gourmet breakfast daily with a selection from hot items and beverages to homemade pastries and fresh fruit. During the afternoon, guests are given pastries and rooms receive a light turnover service. In the evening, guests can treat themselves to a dinner at Alchemy or at the inn’s newest addition Chateaubriand 36, a French-style steakhouse opened in 2022 across the street at the former site of Smithfields Restaurant & Bar.

Ashland.news intern Cameron Aalto is a recent graduate of Southern Oregon University. Email him at aaltoc@sou.edu.

The East Side Inn, now Winchester House, in circa 1913. The structure, originally built on East Main Street in 1886, is listed on the National Register of Historic Places.
Picture of Bert Etling

Bert Etling

Bert Etling is the executive editor of Ashland.news. Email him at betling@ashland.news.

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