Hi there - I am looking for some advice on planning my Oregon trip.
I'll be arriving on Aug 12th in the afternoon:

Aug 12: Portland
Aug 13:
Aug 14:
Aug: 15-16 - Stay in Cannon Beach - or do you recommend a different Coast Town
Aug: 17-20 -- Wilamette wineries and region.

Looking to fill in what to do for the 13-14, and things to do in Wilametter region besides wineries.

Also any recommendations for places to stay in Wilamette or Cannon Beach would be wonderful

I'd stay in Portland for a couple nights--it's a great city and you can also use it as a base for day trips to Mt Hood, the Columbia River Gorge and Mt St Helens.

You might have trouble finding availability in Cannon Beach at this late date and if there is room, many places have 3 night minimum stay requirements in August. So you might need to adjust your stay in Cannon Beach vs the wine region.

As far as places to stay--what is your budget, are you a couple or a family, what type of places do you like? It's hard to recommend something without more information.

Thanks for your quick reply! We are a couple 29/32. So not looking for a huge family, kid scene. We're trying to stay within a budget of no more than $150 a nite. Have you heard of Hotel Oregon in McMinville

Yes, I think it's a cool place so long as you're ok with shared bath (or try to nab a room with a private bath).

For reasonably priced lodgings in Cannon Beach (but remember it's all relative--CB is pretty pricy in the summer), try the Cannon Beach Hotel.

And in Portland you might try the Ace or the Kennedy School in NE Portland (also a McMenamin's place).

I agree with the one who said stay a couple days in Portland. It is a beautiful city. Rose Garden, Chinese area. We stayed at the Courtyard by Mariot, it is scrumptious and right down town.A must see is driving along the Columbia River Gorge. Get off the interstate on 30 early on and stop at the Womens Center overlook, gorgeous view of the river winding thru the gorge. Of course there are many falls you can pull off and see. We started early and ate breakfast at Multanomah Falls Lodge, very good.You can cross over into Washington at the Garden of the Gods Bridge, follow the signs to Skamania Lodge for a great lunch.Then back to Portland.I would recomend Tillamook as a coastal town.

You have received some good information so far. Cannon Beach is a great town, and so books far in advance and most places have the minimum stay. So with that in mind, another option would be to head down to the central coast a bit, and you can cut through the wineries on the way or way back. Newport and Lincoln City do not have the minimum stay requirement, nor the prices that Cannon Beach has, and they have some good beaches.

Hotel Oregon is a fun place to stay. I love the area right around it, filled with coffee shops, stores, restaurants, etc.

The gorge is a great day trip from downtown Portland. Head out on I-84, and at either Troutdale (exit 17) or Corbett (exit 22), get on the old historic highway. Portland Womens Forum, Vista House and Multnomah Falls are the big stops but there are many others that are worthy as well.

The Bridge of the Gods is nice, but my personal preference would be to wander Hood River a bit and then take the back way on hwy 35/26 to Mt. Hood. Stopping at Timberline Lodge, then back to Portland.

The Cannon Beach Hotel is nice, they have a great restaurant there called Gower St. Bistro. If you have trouble finding lodging in CB, check out Seaside, I am there now. It is about 10 minues from Cannon Beach. There is a nice B&B there called the Gilbert Inn, just about a block from the ocean. The Oceanfront Seaside Inn is also a nice B&B with ocean views, right on the prom. It has recently been remodeled and we enoyed a great dinner there this past week. I love the feel of this place and they have an amazing chef in there now, breakfast is included with your room here.

We are going for our daily beach walk now, it's great to be on the coast, I hope you have fun! Any questions on the Cannon Beach/Seaside area feel free to ask! ***kim***

I would (and did) the trip differently.
I would spend the first part of the trip driving to Astoria and then see the coast during the week (you might have better luck with hotels during the week) and then see the
winery region (not that big and not that much to do..more ag area vs Napa style) on the drive back to Portland maybe stay overnight 1 night and then remainder of the time in Portland.
Portlnd has a great Farmers Market this time of year on Saturday, the gardens will be in great bloom and the weather hopefully will be great for a boat ride on the Columbia at teh SeaPort festival.