Lounge on your waterfront balcony—or in front of your in-room fireplace, on cooler nights—at the Waterfront Hotel (from $109), a chic boutique outpost just renovated in 2008. The spot is in Jack London Square, where you can browse the artisan market (Saturdays and Sundays, 10 to 4) and farmers' market (Sundays, 9 to 2).
Escape the rush at the Hills Bed and Breakfast (from $130), a secluded, one-suite guesthouse in the woodsy Oakland Hills area. Complimentary breakfast fare includes granola from Alice Waters’s Café Fanny and apples and tomatoes fresh from the on-site garden. Snag a seat on the outdoor deck for San Francisco Bay views.
Finagle your way into the Bellevue Club (from $109), a private social club set in a 1929 Beaux Arts building. This unpublicized jewel rents rooms to non-members on a case-by-case basis. (Hint: They're usually accommodating if you mention that you're visiting family in Oakland.) The on-site restaurant plans its rotating weekend dinner menu around whatever’s freshest at the nearby Grand Lake Farmers Market.