Set on 113 acres of forest, this little getaway offers 18 over-the-top cottages, each with its own unique theme and (more importantly) complimentary, fully-stocked wet bar. Book a room 35 feet above the ground in the duplex Treehouse or spend the night in a restored 17,000-pound 1968 Sikorsky Sea King Helicopter—retired from flight but perfect for your stay—complete with a chilled bucket of champagne waiting atop the old flight controls and dashboard.
Venture out for dinner at the resort's bar and restaurant (not open to the public), but don't forget to stop at the wine cellar where you can hand-select your own bottle of vino or two.
Food and drink isn't all this place has to offer, so request a stone massage for you and the lady or take a horseback ride through the Litchfield Hills (on second thought, just take the on-site Vespas). Hot air balloon trips and sleigh rides are all options for a night's stay, so make sure you don't spend too much time lying around your treehouse.
Now if they could only arrange for that Sikorsky to take you back to the city...