You will not need to rent a car for the nights you are in Portland. The TriMet lightrail is right outside baggage claim.
When you leave Portland, rent the car downtown.
When you leave the coast go east on Rt. 38 out of Reedsport to see the elk at the Deans Creek viewpoint. In Elkton, turn onto Rt. 138 to go to I-5 at Sutherlin. Go south on I-5 to turn east on Rt. 138 toward Crater Lake - north entrance.
If you cannot get lodging at Crater Lake Lodge, find lodging at Diamond Lake Resort. Spend at least 4 hours in CLNP.
When you leave Crater Lake NP by the north entrance it is 90 miles from there to Bend.
When you leave Bend I prefer the route past Mt. Hood US97/26 and Rt. 35 down to Hood River. Hood River is close enough to PDX that you don't really need to spend the last night in Portland or Sandy. I think you will be favorably impressed with the great state of Oregon.

Judi,

I'm not from Oregon, but we took a very similar trip a few years ago and we loved it. I don't now remember our exact route, but we started in Portland, spent a day driving the Columbia River Gorge to and from Timberline Lodge (we didn't stay there, but did have lunch), then went down the coast and looped back up through Bend. Highlights of the trip:

-- the Columbia River Gorge was beautiful. Multnomah Falls, Mt. Hood, wineries and fruit stands.
-- we went up to Mt. St. Helens while we were in Portland; it's a short two hours north. Stunning.
-- there are lots of farmers markets in Portland. We went to the one on Saturday morning at Portland State University. Huge, colorful, with everything from fruits and vegetables to cheese to bread to flowers.
-- Crater Lake is all you've heard and seen, and more. We did spend two nights in the lodge and it was great.
-- we spent four days driving down the coast. We stayed in Florence (we rented a cottage on the shore, so can't recommend a hotel), then we finished our coastal trip with a night at the Chetko River Inn in Brookings. Remote, private and beautiful. It used to be off the grid, but I don't think it is any longer.
-- Brookings is near the California border, so we continued on south to the Redwoods state and national parks. They're only about 10 miles south of the Oregon state line.
-- we enjoyed both Sisters and Bend, and we enjoyed Corvallis. Nice college town.

You'll have a great time!

Yes, we call ourselves Oregonians

The only problem I see is that your trip is short notice, and so the better places do book up months in advance. So you have your work cut out for you for coastal lodging as well as near Crater Lake.

That said, Cannon Beach is a wonderful little town and I would opt for anything there. Seaside is north of there, but my nicest description of it is tacky honky tonk carnival. Not sure if you have checked out these particular hotels, but the Surfsand, Schooners Cove, Cannon Beach Hotel and Blue Gull Inn are all places we have actually stayed and that I would recommend. Definitely call each place instead of relying on their website, as they may have even 1 free night between other reservations. We head over there often and can get rooms in high season on spur of the moment.

After Cannon Beach, yes, head further down the coast for more time, then as tomfuller mentions, cut over to Crater Lake. The lodge there is most likely booked, but again call, daily even, as there are always cancellations. Other places nearby to look at lodging is the Prospect Inn, Diamond Lake, Mazama Lodge, and also even up around Sunriver. From Crater Lake up to Sunriver is only 90 minutes, and then another 15 or so into Bend. This entire area is one of our favorites and there is so much to do/see!

Since you are interested in Mt Hood, from Bend head up 97 to 26. Again, Timberline fills up quickly, but call. If you can't get a room there at least visit it and maybe have a meal. The closest place to there for other lodging is is Government Camp, a little village towards the base of the mountain. Instead of that though, I would suggest staying in Hood River.

While in this area, absolutely take some time on the old scenic highway. The "big" must stops include Multnomah Falls, Crown Point Vista House, and Portland Woman's Forum (odd name, amazing views).

If you need help with things to do/see, just ask.

Government Camp is near the high point on US 26. There is a Best Western up there if the BW in Hood River is booked.
http://book.bestwestern.com/bestwestern/US/OR/Government-Camp-hotels/BEST-WESTERN-Mt--Hood-Inn/Hotel-Overview.do?propertyCode=38164
I have not been over Rt. 35 lately. The last time there was some construction in several spots.
Sunriver is great if you don't want to go all the way into Bend from Crater Lake. There is also a Best Western (Newberry Center) in the north end of LaPine behind the McD's.

tomfuller--We have stayed at the BW in Government Camp. Very bare bones. It was fine for our purpose, but I really wouldn't recommend it for a vacation.

Agreed - only for 1 night if the other choices such as Timberline and the better places in Hood River are not available.
Please don't go into Sandy and skip the waterfalls.

Thank you so much, Oregonians, and purduegrad! You are appreciated.

I have booked the Inn at Cannon Beach which I know is not exactly in Cannon Beach and the River House Inn (river view) in Florence.

I am allotting two nights to the Crater Lake area but may put off booking as I will try for the Lodge or Diamond Lake Lodge by calling, calling, calling.... I won't wait too long, though.

tomfuller, we do plan to wait until leaving Portland to pick up our car. Thanks for the suggestion to stay somewhere east of Portland on our last night....good idea!

Timberline was still available today; I should book it now.

I was intrigued with Edgefield for our last night but I'm not keen on shared bathrooms.

Thanks again. I am looking forward to our visit to Oregon and know we will have a good time. We are from the east coast so this will be much different from what we are accustomed to.

Judi--Don't let the shared baths put you off. We have stayed there, along with most of the other McMenamin properties and the shared baths have never been an issue. They have plenty, and they are always spotless. We joke that they must have a room with a peephole across from each bathroom and each time someone comes out, they go in and clean it. The Edgefield is a really fun place to stay and uniquely Oregon, so if they have rooms available, I would book it!

Don't let not having a private bath deter you from the Edgefield- it really is a fun place to stay.
Never had a problem getting in to use the BR when I wanted..
If you don't stay at the Edgefield you could consider the Old St Francis School ( owned by the same company) in Bend- old Catholic School turned into a hotel- its fun and unique also and walking distance to downtown Bend.

Yachats is a nice area to stay also- I usually stay at the Adobe- its has ocean views, nice walking path along the ocean and there is also a restaurant with ocean views.

There are 3 hotels/motels in a row- the Adobe, the Fireside and the Overleaf - all on the ocean.

In Florence a nice place to eat is the Waterfront Depot- you will likely need a reservation.
On a nice day I like eating at Traveller's Cove- they have a outdoor dining area overlooking the river- just a casual dining place.

If you don't find a place for Crater Lake - don't hesitate to stay at the Prospect Inn- have stayed there several times. They have a fabulous breakfast in the am and great dinners at night.
The main building of the inn has rooms decorated with antiques, there are several other buildings that are more motel like- not fancy for sure but clean and quiet.

There is a McMenamin's in downtown Bend! http://www.mcmenamins.com/421-old-st-francis-school-home/
It is one of Bend's quirkier inns. Glad you got a room at Timberline.
The reason I suggested Diamond Lake is that it is along your way to go into Crater Lake via the north entrance.
Prospect is on the way into the south entrance from Grants Pass or Medford. Keep trying for a stay at Crater Lake Lodge.

Yes, keep trying for something at Crater Lake. We just returned from our trip to Oregon; we called at 2PM as we were driving to the lake and got a room at Mazama Lodge (another in-park facility). We met another couple that night that arrived at Crater Lake Lodge at 3PM that same day and were able to get a lodge room!

Thanks again. I was able to get a room at the Mazama Lodge - a bird in the hand, so to speak- and will continue trying for the Crater Lake Lodge. At least we will make dinner reservations at the Lodge.

Because the Lodge looks unlikely, I decided to stay at Crater Lake one night and the following night stay in Bend at the Old Francis School; thanks sunbum and tomfuller for that advice.

I have only our last night left to book and it should be Edgefield but hubby gets up about three times a night and isn't sold on schlepping down the hall. I'll do a bit more research...

I am not normally a last minute planner but I think it has worked out this time.

I think there are some rooms at the Edgefield with bathrooms- and if you get one also ask for a room that is not over the area where the entertainment is - have 1 friend who did not get much sleep because of that.

At the St Francis school make sure you find your way to outdoor courtyard behind what used to be the priests garage- if its a cool night they will have the fire pit going and the garage has been turned into a bar- kind of fun area -

Thanks, sun bum; there were no rooms available with bathrooms at Edgefield so we passed on that. I have booked the Comfort Inn...no character but it will do and is close to PDX>

I am done! It took some time but I think I will be happy with my choices.

You all are great! Hugs!!

Being close to the airport will be good - and if you have time you could drop by the Edgefield for a drink or dinner and just do a walk about.

Lots to see and do here- have lived here 20 years now and finding news things all the time.

Now go pack you last minute thing you!

Bookmarking for good info!