• Winchester Inn, Ashland, Oregon

    Bayberry Inn

    Aesthetic Boutique


Billy & Jacqui Mann

Address & Phone
438 N Main St.
Ashland Oregon 97520

City Permit


5 Blocks to OSF Theaters and Downtown Plaza
Central A/C & Heating
Multi Course Breakfasts
Room Service available
Spa service accommodations onsite and off
TV and streaming services in every Room
Indoor/outdoor Fireplaces
On-site Wellness Shop
Preapproved Dogs Allowed
Gourmet multi-course breakfast ·
24-hour Coffee, tea, hot chocolate ·
All Filtered: instant hot water, cold water, and ice
Handmade truffles ·
Garden, front porch, and back deck ·
Large Living room ·
One-of-a-kind art and sculptures throughout
All rooms with en-suite bathroom ·
Rooms with second bed for 3rd guest·
Spa Exclusive Bedding ·
In-room hair dryer and robes
USB charging ports and 6 high speed Wi-Fi boosters
Dedicated off street free parking ·
Secure bicycle storage
OSF Ticket Specials
Snack & Bathroom honor bars
On-site dining at the historic Big Al’s Drive In
Luxury Toiletries created exclusively for The Bayberry by Botanically Fused Formulas
Borrow our bicycles, picnic gear, books, games, plus blankets and cushions for the Theaters!


Vary, available on website.

This beautiful award-winning Inn is a large stately 1920s Craftsman-style home that offers all of today’s amenities while maintaining Ashland’s historic charm.

Greg & Vicki, innkeepers, Iris Inn, Ashland, Oregon

Billy Jacqui Mann


Meet Billy and Jacqui. On-site owners, operators, and your hosts for your stay at the Bayberry Inn. When they decided to follow their dreams and work in the hospitality field, they decided Ashland Oregon was the perfect place. And the beautiful “Bayberry Inn ” would be the ideal location to acquire and continue to run as a beloved B&B, to host their family gatherings on special occasions. Including their eight children and their families. While also, being the perfect facility for their other baby “Oregon Wellness Retreat” (All-Inclusive trips designed for self and relationship nourishment.)

Billy transitioned out of his 25-year career and took his many years of mentoring, business degrees, and his love of supporting and encouraging others into the field of welcoming and hosting, on a more personal level.

Jacqui, after 20 years working as an artist and 8 years in private healthcare for the State of California, jumped at the chance to care for travelers in their time of respite and the chase of enjoying life!

As the “B’s” former lovely owner once told them “This House chooses its owners” …they found that to be true. With much appreciated guidance, knowledge, and encouragement from the community, they vow to uphold the Inns charming history and welcoming reputation. They are honored to be a part of this community and source what they can, locally. Supporting local artisans, businesses, and talents.

Come see, hear, taste, smell, and feel what people love about The
Bayberry Inn. “A Beautiful Retreat for all your Senses”!

© Ashland Bed & Breakfast Network