Oak Hill Bed & Breakfast

2190 Siskiyou Blvd , Ashland, 97520 USA (Show map)


Oak Hill Bed & Breakfast is a 1910 farmhouse and has six rooms with private baths, in-room thermostats, electric fireplaces, Bee Kind soap products, robes, WiFi throughout, and a freshly updated interior. Delicious breakfasts are served in the dining room or in the shade of the oak tree on the garden deck. Breakfasts include juice, seasonal fresh fruit, freshly baked pastries, and inspired entrees. With prior notice, special dietary accommodations can be made. Freshly brewed coffee is set out at 7:30 a.m. each morning. Guests may also enjoy a freshly brewed espresso, cappuccino, latte, or hot tea at any time of day. Freshly baked treats are provided each afternoon. We have private off-street parking for our guests and parking downtown near the theater, on the street or in city parking lots, is free. You can also park in the multi-level garage right behind the Thomas Theater. With the very low garage rate, you may come and go all day. Oak Hill is a five minute drive to the garage. In addition, we are conveniently located on the city bus route for any guests wanting to make use of public transportation. Oak Hill is close to many wonderful wineries, scenic hiking trails, Southern Oregon University, and several other fabulous attractions. We look forward to being part of your Ashland experience!



Write A Review
  • Guest room4.7
  • Service5
  • Value4.9
  • Cleanliness5
  • Onsite Dining5

Oak Hill B&B

5 on April 09, 2018

Brian and Anna are wonderful hosts. The property is impeccably clean and tastefully decorated. Breakfast at the Oak Hill is outstanding, how could it not Anna used to be a baker! We will definitely be staying there in the future.

Innkeeper Response
So glad to hear you enjoyed your stay. We'll have your room ready for you when you return! Don't forget to call about our great theater ticket package deals when you make your next reservation with us. Looking forward to seeing you again!

- Brian (Innkeeper)

Spring Break Fun

5 on April 02, 2018

This was an amazing place to stay over Spring Break this year! Brian and Anna were so hospitable and the house is in the perfect location!

Innkeeper Response
We're so happy you enjoyed your Spring Break with us! And thank you so much for your kind review!

- Anna, Innkeeper (innkeeper)

Charming B&B in Ashland, Oregon

5 on March 20, 2018

Everything about Oak Hill B&B was perfect. The hosts, Anna and Brian, were made to be B&B hosts. They were gracious and accommodating. The room was lovely, with a nicely outfitted bath, and an outstanding view. And the food was amazing. I eat out frequently, and their food, both sweet and savory, was excellent. I will be back again - soon!

Innkeeper Response
Thank you for the wonderful comments about Oak Hill. We absolutely love being able to provide an exceptional experience for everyone who visits us in Ashland. We'll have the treats made, lights on and room ready for you when you return.

- Brian (Innkeeper)

Delightful Innkeepers

4.8 on October 09, 2017

We stayed in Ashland at the beginning of a long road trip and were delighted with our stay at Oak Hill B&B. The Innkeepers were warm and welcoming, great coffee and cookies!

Innkeeper Response
We're glad we could provide you a great experience to start your trip, and we'd love to have you stay with us again! Coffee and treats will be ready for you.

- Brian, innkeeper (innkeeper)

Oustanding place

4.6 on October 03, 2017

Full of Heart place, the breakfast was a daily surprising feast served with smile and joy.

Innkeeper Response
Thank you for your kind review! We welcome feedback and are always looking for ways to improve the guest experience at Oak Hill. We strive for perfection!

- Anna (innkeeper)

You will love it!

4.8 on August 15, 2017

We loved this B&B. Here's why. Anna and Brian are the ideal innkeepers--smiling, caring, helpful, concerned, plus and I need a drum roll here, Anna is a marvelous cook and baker. I can still taste her chocolate chip cookies which were the best I've ever had and I'm a cook and baker, too. Her breakfasts are what dreams are made of. My only note of caution is about the bathroom in the Rose Room. The room is lovely but the bathroom is very narrow, two cannot fit in it at the same time. The other rooms have larger baths. Even in the Rose Room, I would never stay in another inn in Ashland.

Innkeeper Response
Thank you for your review! I'm so glad you enjoyed the food here at Oak Hill! Brian and I both love cooking! The bathroom in the Rose Room is a bit narrow, but that's the nature of an old home. Bathrooms are sometimes tucked into small spaces. I'm so glad you enjoyed your stay and we look forward to seeing you again!

- Anna (innkeeper)

Ashland romantic weekend

5 on August 06, 2017

Oak hill Bed and Breakfast is a great place to have a romantic weekend. It has charming rooms and very comfortable common areas. Anna's breakfasts were delicious and her afternoon treats were great! It also has a beautiful gardens. It is a great place to stay and enjoy all Ashland has to offer - especially the Oregon Shakespear Festival.

Innkeeper Response
Thank you for giving us the opportunity to host your romantic weekend in Ashland. We're so glad you enjoyed your stay with us!

- Anna (innkeeper)

A wonderful stay at Oak Hill!

5 on July 29, 2017

Oak Hill provided a much need respite on a long trip. Anna and Brian were amazing! Staying in the Garden Room was peaceful and tranquil. Already planning to come again next time through Ashland and of course, to stay longer. Our breakfast was fabulous. Plus Anna's cookies and brownies were a special treat to take with us as we continued our journey. Thanks so much Anna and Brian for making us feel at home.

Innkeeper Response
We do hope to see you again and we're so glad you enjoyed your stay with us! You're welcome any time!

- Anna (innkeeper)

As always, wish we would have stayed longer !

5 on July 18, 2017

Anna and Brian were exceptional during our stay. This was our second trip to Ashland in a week and our first stay at Oak Hill. We were late arriving but all was well. We stayed in the garden room which was absolutely charming and peaceful. Breakfast was incredible! Our cookie and brownie for "the road" hit the spot for our mid day break later. Cannot wait to come back to Ashland and stay here again. Thanks so much Brian and Anna!

Innkeeper Response
Thank you for your kind words! We're so glad to have had the opportunity to host you in Ashland and we hope to see you again!

- Anna (innkeeper)

View More Reviews

Rooms & Rates

Artisan Market

This room faces east and looks out on an ancient oak and the garden deck. The comfortable queen bed is tucked into a charming and peaceful alcove. Enjoy a glass of wine as you relax in your quiet corner of the house. (previously the Fern Room)

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

Nightly Rate: $130 - $205


The corner windows of this room face the foothills of the Cascades and the Siskiyou Mountains. The view is enhanced by a towering Douglas fir just outside. Relax on the settee by the fireplace and catch up on your Shakespeare. (previously the Lilac Room)

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

Nightly Rate: $130 - $205

Grizzly Peak

Enjoy the best view in the house while relaxing in this cool and spacious room on the second floor. This room features a window wall facing the Cascade Mountains and a fabulous view of Grizzly Peak. Catch a glimpse of the Acorn woodpeckers residing in the oak tree in the front yard. (previously the Iris Room)

  • Maximum Capacity: 3
  • Bathroom Private Bath
  • Beds 1 King , 1 Twin

Nightly Rate: $155 - $230


This room on the first floor has a queen bed and a twin to provide for three guests. A large window looks to the oak tree in the front yard and north to the Siskiyou mountains. The Elizabethan opens out to the living room and is closest to morning coffee. This room is the most accessible room in the house. (previously the Oak Room)

  • Maximum Capacity: 3
  • Bathroom Private Bath
  • Beds 1 Queen , 1 Twin

Nightly Rate: $105 - $205

Lithia Park

Surrounded by flowers and light, the Lithia Park Room definitely feels like it is part of the garden. This room has its own private outside entrance and patio. Hummingbirds will greet you in the morning as you take the short pathway to an exquisite breakfast. Guests love having the garden at their doorstep. (previously the Garden Room)

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

Nightly Rate: $140 - $215

Ashland Creek

This is a sunny upstairs room overlooking the garden and facing the deeply forested Siskiyou Mountains to the south. The corner mantel with electric fireplace feels comfortable and inviting. Curl up and read a book by the fire. (previously the Rose Room)

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $140 - $215

Check Dates


Location Type

Oregon Shakespeare Festival , Mountains, Small town, Wine country


Medford, OR (MFR-Medford-Jackson County) 19.4 miles

Directions to property:

Get on I-5 S from Biddle Rd and OR-62 W. Follow I-5 S. Take exit 14 from I-5 S. Turn right onto Hwy 66, left on Tolman Creek Rd. and right on Siskiyou Blvd. https://goo.gl/maps/YsxvFST8FqM2

Area Attractions

Antique Shopping, Concert venue, Eco-tourism, Gourmet/Fine Dining, Lake, National/State parks, Nature area, Oregon Shakespeare Festival, Performing Theater, River, Ski area, University, Vineyard, Winery

Inn Details

Establishment type


On-site amenities

Board games, Coffee/Tea facilities, Computer, Desk, Fridge, Library, Parking, Piano, Telephone, Walk to mass transit , USB charging ports on alarm clock

Room amenities

Air conditioning, Alarm clock, Amenities Basket, Bath robes, Ceiling fans, Fireplace, Hairdryer, Ironing Board, Private entrance, Wi-Fi

Check Dates


  • Check In:: 15:00
  • Check Out:: 11:00
  • Open All Year Round: Yes
  • Smoking Allowed: No Neither smoking nor vaping is allowed inside the property.
  • Drinking Allowed: Yes
  • Alcohol Provided Yes
  • Suitable For Children: Limited Exceptions can be made in some circumstances. Please call.
  • Childcare Provided: No
  • Guest Pets Allowed: No
  • Disabled Access No

Terms and Conditions



Anna & Brian Runyen

Languages spoken


Resident Pets

About the innkeepers

Texans Anna and Brian, having found a new home in the enchanting town of Ashland, look forward to sharing their love of food, wine, travel, photography, theater and friendship. Anna is a former elementary school teacher, school librarian, professional baker and cake artist. Brian is a civil engineer and professional photographer. Anna and Brian have a shared passion for food and will both be working in the kitchen making delicious culinary creations for Oak Hill's guests.

Check Dates




  • Time Served: 8:30-9:30 a.m.
  • Serving Location: Garden Deck, Dining Room

Special meal options

Low fat , Restrictive , Vegetarian gluten-free, dairy-free, vegan, etc.

Signature Dish

Southern Eggs Benedict
We have a southern twist on Eggs Benedict at Oak Hill. We serve our poached eggs on top of sweet cornbread and smoked ham and then drizzle a cheddar hollandaise sauce on top. We garnish this dish with chives and roasted corn. Delicious!