ON-PROPERTY VS. OFF-PROPERTY
At Walt Disney World, on-property resorts include the Grand Floridian and Contemporary Resort, among many others across every price tier. At the Disneyland Resort, the Disneyland Hotel, Grand Californian, and Pixar Place Hotel are the three Disney-owned properties.
Almost always. Off-property hotels near both resorts — including partner hotels like Universal's Cabana Bay Beach Resort — are typically 30–60% cheaper than comparable on-property rooms, though you give up early park entry and free Disney transportation.
On-property guests typically get an earlier park entry window, access to Disney transportation (monorail, buses, Skyliner at Walt Disney World; a short walk at Disneyland), and slightly earlier booking access for dining and Lightning Lane reservations.
COSTS
Most Walt Disney World resorts do not charge a separate mandatory resort fee, but self-parking and valet are billed separately at many properties. Always compare the total cost including parking, not just the nightly rate.
Late January through mid-February and September through early November are historically the lowest-rate, lowest-crowd windows at both Walt Disney World and the Disneyland Resort.
PLANNING
Walt Disney World resort reservations open up to 11 months ahead for package bookings. Disneyland-area hotels don't have as strict a window, but the most requested rooms (like the Grand Californian's park-view rooms) still sell out first.
At Walt Disney World, no — Disney's free transportation network covers the resort. At the Disneyland Resort, a car isn't needed for the parks themselves since everything is walkable, but is useful for day trips to nearby beaches.