4. Insider's Tip
Big family hotels like the Driftwood in Amagansett and the Surf Club in Montauk close from October through May, and what’s open in the off-season is usually couples-oriented and expensive. The best value and most comfortable option may be to rent a house by the week. Michael Kaufman of Accommodations Plus offers three- and four-bedroom homes in East Hampton with prices starting at $1,700 for a week. Kaufman can arrange for cribs, strollers, high chairs, and bikes, as well as reservations for charter fishing boats and golf tee times.