Dermot and Sally O'Brien, the innkeepers of the Bayberry Inn, provide an oasis in Ashland where you can have needed private time away from the plays in either the inn's beautiful rooms, living room, patio, or lawn. The breakfasts are delicious too.

We have attended the Oregon Shakespeare Festival and stayed at the Bayberry Inn every October for the past seven years. The Bayberry is well located and within an easy 10 minute walk of the theaters and restaurant area. Dermot and Sally are delightful and knowledgeable hosts (providing info about local restaurants, shopping, and events), and I particularly like hearing their... More

I planned a romantic trip to Ashland with husband. Looking online I found this B&B which was reasonable priced for the area and the good reviews. I emailed the owner, Dermott indicating my room interest and date and I heard nothing back. I then followed up 1 week later with a phone call. Dermott saw my email and room request... More

Traveling to Oregon and points beyond we frequently stay in Ashland. Not necessarily for the Shakespeare Festival but usually just for the great food and some well deserved R&R. Recently we found ourselves heading that way and I started calling some of our favorite places to stay. Guess what ? everything was booked… I found the Bayberry Inn and was... More

As a family with two teen boys we always struggle a little with accommodations when we're on vacation. One hotel room with two beds is cramped; two hotel rooms is expensive, suites and apartments can be hard to find (and sofabeds are often uncormfortable). The two-bedroom cottage at Bayberry Inn turned out to be a terrific place for our family... More

I am planning to stay at the Bayberry Inn in Ashland this summer. Reading the reviews, I am having mixed feelings. What is served at breakfast?

My friend Mimi and I stay at the Bayberry Inn every year while we attend the Shakespeare Festival. Sally and Dermot, the innkeepers, are wonderful hosts and see to our every need. The inn is beautiful and there is a terrific patio for reading or catching some rays. The inn is just a short walk to the plays and restaurants... More

Shakespeare Festival has brought us to Ashland for many years. We have stayed in three B&Bs with Bayberry being the third. We have never ceased booking here since that first time. We were hesitant when the former owner sold, but upon meeting the new owners, we knew we would continue our annual bookings. The innkeepers are both warm and inviting... More

We recently visited Ashland for the second consecutive year, both times we stayed at the Bayberry Inn. You can not go wrong lodging here. The house is convenient to town ( 10 minute walk), the rooms are quiet, exceptionally clean, and the house is warm and comfortable. The owners are fantastic. The perfect balance of hospitality and professionalism. Everyone is... More