luxury seaside property for rent Orient, United States

Your quintessential North Fork summer starts here. Tucked away in the quiet beach community of Paradise Shores, this Bayfront cottage is the summer retreat you’ve been dreaming of. Positioned directly on Southold Bay with unobstructed views of Shelter Island, this charming cottage offers the best scenery on the North Fork. Whether you're hosting a sunset dinner or just enjoying a quiet morning, the backdrop is always spectacular. Loaded with vintage charm and coastal energy, it’s a place where the days are measured by the tides rather than the clock. The first floor features a waterfront sunroom, cozy living room, galley kitchen, two bedrooms and a full bath. For ultimate privacy, escape to the second floor, featuring a primary suite with a dedicated sitting area -the perfect perch for morning coffee- and half bath. Step outside to your own secluded paradise where you will find a waterfront deck offering the perfect space for al fresco dining, stargazing, or simply watching the boats pass by. It’s the ultimate front-row seat to the island's beautiful golden-hour. This property has all the markers of a perfect North Fork getaway. Permit #1435. Available Memorial Day-June 30: $18,000, July 1-31: $20,000 and August 1-31: $25,000.

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