Location: Winvian Resort, Litchfield, CT
Cost: From $950 per night
For high-flying financiers, this may be the ultimate soft landing. This hangar-like cottage has a 17,000-pound, fully restored 1968 Sikorsky helicopter as its centerpiece. Inside the decommissioned Coast Guard copter you’ll find a lounge, bar and entertainment center, and the original cockpit, where guests can play “pilot.” Surrounding the aircraft are plenty of creature comforts: an oversize tub, fireplace, and a cozy bedroom area. The Winvian Resort, by the way, has Wall Street in its DNA: It was once a farm owned by Merrill Lynch co-founder Winthrop Smith. The property is still family-run.