Average Rate: $10,000 per night; ~$30,000 for a three-night weekend stay

Managed by Rental Escapes, this six-bedroom, seven-bathroom home, located on over eight private waterfront acres on a peninsula overlooking Fishers Island Sound, boasts 10,000 square feet of pure luxury, including amazing water views from almost every room.

The charming village of Stonington with restaurants and shopping is a short distance away, but you’ll find plenty to do at this lavish estate, too. Activity options include enjoying a leisurely morning walk in the private garden, taking a dip in the 30′ x 60′ saltwater pool, relaxing in the heated spa, perusing the 2,000-bottle wine cellar and enjoying a movie in the estate’s theater room.