Portland to San Fran

Im currently planning a trip for five of us travelling down the westcoast of the US starting from Vancouver. Where doing this trip just after christmas so it will be winter time travelling.
While we have already decided to stop in Seattle and Portland, what i was wondering is where would be a popular or nice place to stop somewhere between Portland and San Fran to stay overnight in and break up the trip nicely.
I've had a rough look on maps to see what cities are about halfway between Portland and San Fran and was looking at around Crescent City, Ashland, Medford.... but have no idea what these places are like. We had been recommended visiting the redwood forest national parks on the way so if it close to that, that would be great to.
Any recommendations on cities to stop in or even places to stay would be most appreciated.

Thanking you.

Welcome aboard the RoadTrip America Forums!

First things first - make sure that when you set up your rental car that it is allowed to cross the border. If you are doing a one-way rental from Vancouver to San Francisco, this will probably be included, but be prepared to pay an additional premium (on top of the normal one-way drop-off charge) because the car will need to be insured in two countries. You can probably save yourself a lot of money by getting to Seattle by alternate transportation before picking up the car.

Of the towns you list for a possible halfway stop, the only one I'm familiar with is Ashland. It's a bit far inland for your purposes, but due to its Shakespeare festival (NOT on while you'd be in the area) it should have an abundance of accommodations. Crescent City would be a better stopping point if you're looking to get a good jump on seeing the redwoods AND making it to San Francisco in one day.

Finally, you should have a look at these two threads (Thread_1 and Thread_2) to get you started on what's available along the Pacific Northwest coast. You will have to keep an eye on the weather at that time of year, but rain is just as likely as snow, except when crossing the mountains.

AZBuck

From Portland to San Francisco you have 2 main choices: Interstate 5 (inland) or Highway 101 (coastal). I have made this trip several times in the past 5 years since I've moved from CA to OR. For a tourist there is no question but that you want the coastal route. The inland route via I-5 is straight and unexceptional except for a very few spots such as Mt. Shasta and Lake Shasta in far N. Calif.

The town of Charleston near Coos Bay, OR is featured in the current copy of Oregon Coast Magazine because of it's excellent seafood restaurants. I have not been there, but am planning to go soon myself.

There are many small towns on the central and south coasts of Oregon that are worth seeing. South of Florence is the Oregon Dunes area where you can ride the sand dunes in a rented dune buggy (take it easy!) This area is rugged and quite rustic and very beautiful. If you're a lighthouse lover, this is your state! I suggest that you drive south on 101 and just stop when and where the urge tells you to stop. Be aware that we have had an excess of rain recently and there is some flooding in the Tillamook County area of N. Oregon (WA has had even worse flooding).