I might be a bit biased since I lived in the Northwest district, but my recommendation would be that area. As you’d expect, hotels are going to be a lot more expensive the “closer in” you are. There are a couple hotels near NW 23rd and NW Vaughn (Holiday Inn Express and Silver Cloud Inn). I’m sure there are some good VRBO’s or whatever in this area as well. These are in a good spot since you’d have easy access onto the freeways, you’d be less than a mile to Forest Park, and you can easily walk (or take the streetcar) to explore downtown, NW 21st/23rd and the pearl. If you are looking to save a bit more money, check out Beaverton. Just try to stay not too far south from 26th and not too far west from 217 to save yourself time siting in a car. In terms of driving.
In terms of what to do, you are picking the perfect time as it’s one of the few months where it is dry.
Run: Forest park should be top on the list. There are so many good trails, Wildwood is the longest and most popular. It’d be best to run it on a weekday as it can get crowded on the weekends. I’d also do a run on the waterfront. Do something like a loop where you cross the Broadway Bridge run down to the Tillicum Crossing, then run back. Lots of good people watching, nice city views. If you are up for it, go all the way down to the Sellwood Bridge before looping back. Other good places to run include Washington Park, Terwilliger, Tryon Creek Park, Mt Tabor, Powel Butte, and a number of trails in Beaverton if you stay in that area (Nike, Fanno Creek, etc)
Ride: I posted on a thread awhile back of good places to ride which you can probably find. My favorites: (1) Historic Columbia River Highway (Troutdale to Horsetail Falls or Hood River to the Dalles….google Image the Rowena Loops); (2) Sauvie Island; (3) Skyline .
Hiking: There are an endless amount of great hikes. My favorite is probably Eagle Creek to Tunnel Falls stopping at Punchbowl Falls along the way (12 miles round trip). The waterfalls and viewpoints along the Columbia River Highway starting from Troutdale (each one is pretty short….and pretty crowed….if you want to go to Multnomah, go on a weekday and go really early). Mt Hood/Trillium Lake. Silver Falls (about an hour south of Portland), there are also some good ones about an west of Portland as you head towards the Coast but I can’t remember of the names right now. Speaking of the coast, if you haven’t been, take a day to go. Cannon Beach is just an hour-ish drive close and has some really gorgeous spots.
Other: Portland loves it’s good so there is no shortage of great places to eat. One of the local “chains” is called McMenamins. They buy old buildings and turn them into restaurants, bars, concert halls, etc. Each one is unique. If I were to pick one to check out it’d be Kennedy School. They took an old grade school and put in a restaurant, hotel, bar, movie theater, and a few other things. Get ice cream at Salt and Straw (be prepared to wait in line for a bit), get a doughnut at Blue Star (and you should probably get one at VooDoo as well since it’s kind of a must for tourists), if you can catch a Timbers soccer game and try and sit close to the Timbers Army. Stroll around and check out the shops and restaurants in the Pearl, NW 23rd/21st, downtown, N Mississippi Ave, Hawthorn, and Alberta.
That’s about all I can think of off the top of my head.
Matt