Hi Trey!
While there are many good offsite hotel options near Walt Disney World, there are many amenities such as free transportation, Extra Magic Hours and package delivery just make it worthwhile to stay on property. There is never a good time to not go to Disney, but for cooler weather and lighter crowds go anytime when school is in session. During school holidays the parks often become more crowded and resort room prices are also higher. The weeks between Thanksgiving and Christmas are good time to go because of the cooler weather, lighter crowds and lots of festive decorations. Mid January through mid February is another good time, but there are a lot of refurbishments done during these months so make sure to check if your favorite attraction will be open.
Disney offers different types of discounts so it's always best to check the
special offers page to see what new ones are available. The Swan and Dolphin hotel is offering a room discount for teachers right now with rates starting at $149, though not Disney owned, guests enjoy many of the same amenities such as Extra Magic Hours and Transportation.
Disney has a current promotion for military (active and retired) where guests can purchase up to (6) four day park hopper passes for just $156. Disney is also offering a discount of 30% off Value Resorts, 35% off Moderate, and 40% off Deluxe resorts from now until September 28 for active and retired military. Shades of Green is a military resort on property that also has really great room rates based on a sliding scale according to your rank, it also offers some wonderful amenities to it's guests.
Please visit us again if you have anymore questions!
Mandy