luxury seaside house for rent Cutchogue, 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.

Classic Cape Cod Retreat Near Shell Beach Enjoy summer on Shelter Island in this charming Cape Cod–style home with tranquil water views just across the street and easy access to one of the island’s most popular beaches. Located less than half a mile from Shell Beach, this 4-bedroom, 2.5-bath home is set in a friendly, sought-after summer community. The bright, open living and dining area flows seamlessly to a spacious deck, making it ideal for outdoor dining, entertaining, or relaxing after a day at the beach. The spacious kitchen features warm oak cabinetry with white countertops, offering a classic, functional layout that complements the home’s Cape Cod style. The first-floor primary bedroom provides a private and comfortable retreat, ideal for easy living and added convenience. Upstairs, three additional bedrooms offer plenty of space for guests. With nearby beach access, and island activities that Shelter Island has to offer, this home is a wonderful seasonal escape for relaxed coastal living.

Sound Front Contemporary Octagonal Home with Private Beach. Contemporary and chic, mint condition 1970's modular octagonal home located on a breath-taking sound front walk-out private beach in Orient. Three bedrooms, each with a full bath and an additional powder room. Updated kitchen and bathrooms. Every room is furnished with period mid-C style furniture. Living room has original Malm wood burning fireplace. Many spacious common areas, including glazed porch connecting the two octagonal wings. Relax on the large water-side deck with hot tub while enjoy panoramic water views from every room. Offered June $15,000; July $35,000; Aug $35,000; Sept $20,000. Permit #0465.

Located just outside Bridgehampton village sits this quiet cottage available for summer and off-season rental. Tasteful amenities include a large living room with fireplace and vaulted ceiling, a separate kitchen with washer/dryer, a dining area, two bedrooms and a full bath. A charming patio allows for outdoor nature enjoyment, all within minutes of local area shops, restaurants and ocean beaches. [[Rental Registration # RP241102]] EH RR #: RP241102 Rental Terms: Winter Season: $30,000 Per Month June: $15,000 Memorial Day - Labor Day: $60,000 July: $25,000 July - Labor Day: $50,000

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.

Stunning waterfront shingle style home overlooking Long Island Sound with private beach access. Waterview, heated pool. Wrap-around porch. Original beach stone fireplace, vintage beadboard walls, large, updated gourmet kitchen, open common area, 5 bedrooms, 3 bathrooms, large master ensuite with private screen water view balcony. Beautiful interior furnishings, with teak rocking chairs, chaise lounges and picnic table on porch and pool area for entertaining. Close to Orient Village amenities, marinas, Country store, Yacht Club, and bay beaches. Offered June 3-27 $28,000; Sept 2-16 $14,000. Permit# 1108.

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.

Situated in the quaint hamlet of Remsenburg on charming south of the highway Rogers Lane, this fully furnished home is privately nestled on a 1.39 acre waterfront property and completely renovated. The home offers an airy double-height living room with a new propane fireplace, open floor plan, 4 bedrooms, and 2.5 baths. Sliders in the living room and the dining room lead out to the sunny, spacious deck with inground heated pool, Weber grill, outdoor furniture and gorgeous views of the backyard oasis. Enjoy your own private cat walk to the water. 90 minutes from NYC, 10 minutes to village shopping, dining and beautiful beaches.