I deleted a few I was totally clueless on... Some of these places I've never been to. Others I absolutely love.
Alaska: A place on a lake or a fjord I can fly a plane onto.
Arizona: I've heard Sedona is nice.
Arkansas: Wherever Erik Estrada advertises.
California: Marin County.
Colorado: Aspen.
Connecticut: Mystic.
Delaware: Rehoboth I guess.
Florida: I'd like to have my own key/cay.
Georgia: Savannah or Jekyll Island.
Illinois: Chicago.
Indiana: South Bend?
Maine: Portland.
Maryland: Annapolis.
Massachusetts: Nantucket.
Michigan: I'd find a cool lake town.
Minnesota: See Michigan.
Mississippi: A nice shore town, but not a casino area.
Missouri: St Louis?
Nebraska: Near the pedestrian bridge.
Nevada: Tahoe.
New Hampshire: Conway vicinity (Saco River).
New Jersey: Ocean City.
New Mexico: Santa Fe.
New York: North Fork.
North Carolina: Ocracoke.
Oregon: A nice coastal area.
Pennsylvania: upper Bucks County.
Rhode Island: Block Island.
South Carolina: Charleston.
Tennessee: Somewhere nice but not as touristy as Gatlinburg.
Texas: Hill country.
Vermont: Almost anywhere. Bennington is nice.
Virginia: Horse farm outside Charlottesville.
Washington: Sequim.
West Virginia: Harper's Ferry.
Wisconsin: I've heard Door Co is nice.
Wyoming: Brokeback Mtn.