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 [email protected].

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 [email protected].
Siskiyou Woodcraft Guild Harvest Show of fine woodworking OSF Hay-Patton Rehearsal Center across from Ashland Springs Hotel Ashland Oregon

Related Posts...

Our Sponsors

Camelot Theatre Hansel and Gretel Talent Oregon
Siskiyou Woodcraft Guild Harvest Show of fine woodworking OSF Hay-Patton Rehearsal Center across from Ashland Springs Hotel Ashland Oregon
Paddinton Station Holiday Open House Ashland Oregon

Latest posts

Our Sponsors

Siskiyou School's Winter Faire Festival and Holiday Market Ashland Oregon
Literary Arts The Moth Arlene Schnitzer Concert Hall Portland Oregon
Conscious Design Build Ashland Oregon
Ashland Community Composting Ashland Oregon
City of Ashland Public Notice Ashland Oregon

Explore More...

This bonus “variety” puzzle is an acrostic with a quirky quote about newspapers -- in support of year-end fundraising efforts. Solve it in your browser or download and print; how to solve acrostics. Next Friday's crossword: Turkish Delights #03. Check out the Mini crossword on Tuesdays.
As of Nov. 3, Ashland Community Food Bank has a new director at the reins. Catie Mahoney will serve in the role with guidance from outgoing director Amey Broeker, who will officially retire on Dec. 31 after serving in the food bank role since 2022.
The Ashland City Council will review a proposal from a potential provider to oversee its extreme weather shelter during its regular business meeting on Tuesday, Nov. 18.
The Ashland Independent Film Festival has added a second screening showcasing Indigenous filmmakers on Sunday, Nov. 23.
Three and a half years into the war with Russia, Ashland violinist and longtime music teacher Faina Podolnaya is still finding ways to help Ukrainian refugees.

Don't Miss Our Top Stories

Get our newsletter delivered to your inbox three times a week.
It’s FREE and you can cancel anytime.

ashland.news logo

Subscribe to the newsletter and get local news sent directly to your inbox.

(It’s free)