Encapsulation complexes of hexyl- and cyclohexyl-halides in water soluble cavitands with urea rims have been investigated by DFT calculations. In agreement with experiment, the most stable conformations of the different encapsulated halides have the halide at the rim of the cavity, or "up". The possibility of halogen bonding of Br to the resorcinarenes of the cavitand is suggested by the near degeneracy of "up" and "down" conformations found in encapsulated bromides. In the calculations, in addition to the implicit inclusion of the solvent, explicit addition of water molecules at the rim of the tetra-urea cavitand is found to be necessary.