Why drive when you can take public transit Bart would be the way to do it Parking in SF is expensive
Can you not stay in SF and pay with points. If you are in Oakland downtown it will be faster than SFO by BART. Please read reviews of the hotels and check the area if not in downtown Oak.
Downtown Oakland would also be more interesting than SF Airport areas.
Make sure though, any Oakland location is not at the Oakland Airport area, as those places are rather remote and not close to the safest areas in town.
Check with us when you get closer to a couple of hotels to choose from and we can tell you more about their locations.
To strictly answer your title question: Neither.
But I suppose Oakland is a faster and cheaper trip into SF. What hotel points are you using?
To be really honest, I'd suggest looking at other California destinations which might have better options. Because to come to San Francisco but not stay in the city is not an optimum solution.
You can hop on BART and be in SF in a few minutes, will cost about $3.00 each direction, plus MUNI. Staying in Oakland would make for a quick trip into SF and back, but not necessarily cheap. Driving into SF each day means paying bridge toll plus parking, which can add up.
You can't use your hotel points in San Francisco?
What hotel points are you using? I would strongly advise for this trip to stay in San Francisco. If there is no place you can use your points, I would save them for another trip rather than commuting back and forth from Oakland or SFO.
I completely agree with RamblinSal "Because to come to San Francisco but not stay in the city is not an optimum solution."
Oakland to SF via BART is 10 to 25 mins Depending on location. Shorter than Staying by SF0.
Different levels of hotels use different levels of points - sometimes by a huge range (for example, in the Starwood program you can get a hotel anywhere from 3,000 pts per night up to 40,000 or more for luxury properties- and most hotel chains are similar). So maybe he only has enough to cover the requirements of one of the airport hotels.
I agree, also some major chains (usually lower end) opt not to have Hotels in the City of San Francisco due to high costs of land and labor, and have standards like free breakfasts, free parking, etc.
While staying in the "city" is nice, I have spent many times in the Bay area using a location outside the city of SF. There are plenty of options to using public transit, BART and many more. Yes, they cost money, and take time. But if not all your focus is checking out the "City", but also the other many amazing places in the larger San Francisco Bay Area, a Hotel/Motel away from the city does make sense. There is not just "one" answer...
Knowing exact locations of the hotels you're considering would help.
BART quickest from Oakland, but at least once you could take the ferry to/from Jack London Square. Great views of the SF skyline.
Thank you for the responses so far. Several of you get it that I would love to stay at one of the Marriott, Hilton's, etc. in the Wharf or downtown San Fran, but they charge so many points that one night would exhaust what I have and then paying their $250-300 night rates for the other two nights would be harsh compared to paying nothing for 3 nights a little bit away. That's why I asked if I have to choose between the 2 locations. It seems there are several options in Oakland not far from that Jack London square. So, it sounds like that will be the better choice and to take the transportation rather than drive. Would those who responded agree with this conclusion?