Upvote:6
It works just fine on sites like Orbitz and Expedia. Im not quite sure what your problem is.
For Orbitz: Click on "packages" and put the "small town" into the "fly to" field. You will be first asked to select the hotel in "small town" and then the flights to the nearest airport.
Although you can book this as a package, it's typically much easier and cheaper to book flights and hotels separate. The package savings are minimal and you typically get a better deal when optimizing separately.
(No endors*m*nt or advertising intent): I typically use hipmunk.com, since it has much better flight search display than most other websites and does a good job in reducing the "noise" of flights options that are just worse versions of an existing option.