luxury seaside properties for rent New York, United States

Waterfront retreat in the coveted Fleets Neck community of Cutchogue. Nestled along a tranquil creek, this charming 2 bedroom, 2 bathroom cottage offers a peaceful setting with beautiful water views, spectacular sunsets, and the perfect backdrop for a North Fork escape. Enjoy kayaking, paddleboarding, fishing, or simply relaxing by the water, all while being moments from the neighborhood’s beloved beaches. Located within the sought-after Fleets Neck community, tenants can enjoy proximity to Fleets Neck Beach and Pequash Beach. Ideally situated near renowned vineyards, farm stands, waterfront dining, marinas, and all the charm of North Fork living, this inviting cottage offers the perfect blend of waterfront serenity and convenience. Available for September and October 2026, as well as an off-season rental opportunity. Whether you’re seeking a fall getaway, seasonal retreat, or extended stay on the North Fork, this waterfront cottage is a rare opportunity to experience the best of Cutchogue’s coveted Fleets Neck waterfront lifestyle. Availability: September $3,000, October $3,000 or off season rental for $2800 per month

Paradise on the bay!! Relax and enjoy your vacation at a quintessential bayfront beach house directly across the street from one of the most beautiful ocean beaches on LI. Enjoy your morning coffee inside your screened-in porch as the bay gently laps against the bulkhead 20 feet away. Spend your days enjoying the ocean beach, paddle-boarding or kayaking on the bay or visit the quaint and recently renovated main street just 2 miles away. End your day gazing at the most unforgettable sunsets. This single story home includes three bedrooms (two with queen-size beds and one with bunk beds), one full bath and a outdoor shower to wash off the day's salt and sand. The updated kitchen is great for cooking at home; or you can barbeque on the expanded deck out back. Now available for end of summer and fall 2025.

Charming historic Bayfront beach cottage located on Orient Harbor in Orient Village. Featuring 75 feet of private walkout beach, waterside porch, screen bay view gazebo for entertaining. Interior includes wide plank wood floors, renovated baths, spacious kitchen water view living room with wood burning fireplace, 2 ensuite bedrooms for a total of 3 bedrooms/ 2.5 baths. Walk to Country Store, Post Office, Orient Yacht Club, marinas, and other village amenities. Close to renowned Orient Beach State Park & Cross Island Ferry. Available Aug $35,000. Permit# 1374. No showings until after January 15, 2026.