luxury houses for rent Greenport, United States

Relax and enjoy this beautifully appointed bay front house w/ private beach and stunning views of Orient Harbor, Bug Light and Shelter Island. Moor your boat in the bay; kayak, swim, fish or chill on the decks and porches. Basement game room w/ Ping-Pong, TV and games. Conveniently located near shopping, restaurants, ferries, farm stands, vineyards.

Bayfront beach Cottage with panoramic views, stylish & chic. Great room with newly renovated kitchen, dining area, living room, bay side deck. Master bedroom & bath and additional guest bedroom & full bath, outdoor shower, private beach. Offered Nov 2023-March 2024 $4,000/mo.; 2024: Apr $4,500; July $14,000, Aug $16,000, Aug-LD $17,000; Sept $9,000; Oct $5,000. Permit# 0569.

Relax, rejuvenate and recharge in this updated North Fork gem with new kitchen, outdoor deck, screened in porch and large fenced in yard. Three bedrooms and full bath on the 2nd floor. Located on a quiet road but still close to beaches, farm stands and local vineyards! $6,500 per week. 2 week minimum.

Not available for year round rent at this time. Newly renovated three bedroom, two bath bungalow just outside of popular Greenport Village.This house provides a sense of privacy and relaxation close to the beach. Located less than one mile away, the captivating Rocky Point Beach is a picturesque retreat for everyone to enjoy. Additionally, there is the exquisite Truman's Beach nearby, which provides a stunning view of Connecticut. Lavender Bay and Sep's Farm are conveniently located only 0.4 miles away.The exterior of the property is designed for entertainment, featuring a spacious patio, barbecue area, fire pit, and even an outdoor shower to refresh after a dip in the nearby beaches.

Charming and chic 3 bedroom, 1.5 bath Cottage on Lake Marion with many charming original features. Open, sunny floor plan with common area that opens onto spacious lakefront deck perfect for relaxing, grilling & dining. Wood burning fireplace, fully equipped cook's kitchen, private dock, outdoor shower, & easy stroll to association bay beach. Offered June $8,000; Aug 15-LD $9,000. Permit# 0692.

Experience the ultimate North Fork summer with the perfect combination of comfort and privacy in this spacious 4 bedroom home with heated pool on 3.5 acres. Explore the pristine beaches, beautiful vineyards and breweries or check out one of the many chef renowned restaurants the area has to offer. This property is the ideal retreat for a memorable summer getaway on the North Fork.

Escape to this 4 bedroom, 3 bath waterfront North Fork Retreat with expansive views across Hashamomuck to Peconic Bay. The back yard features a deck with private stairs leading down to the water, perfect for kayaking and paddle boarding. End the day entertaining around the fire or with a sunset stroll on your deeded Long Island Sound beach just a block away. Make this home your jumping point to enjoy the beaches, parks, restaurants, vineyards, farm stands, golf courses, and the many other activities the East End has to offer. The list is endless and is awaiting your arrival! Rental Permit #0477

Great location, this home is just blocks from beach access. Come enjoy this centrally located property!

A light, bright and mint condition Orient Village 4 bedroom, 4 bath bayfront home, featuring beautiful classic lines and architectural details throughout. Walls of windows and high ceilings showcase stunning sunsets over Orient Harbor and beyond. Gourmet kitchen, open floor plan with glass doors to outdoor dining area, waterside lawn, two decks and stairs to the water makes this a perfect opportunity for entertaining and family relaxation. Rental includes a gas grill, 2 boat moorings and nearby association sandy beach. This very well appointed home includes an open fireplace, perfect for an extended stay throughout the fall and beyond in an idyllic location that beckons peace and relaxation surrounded by nature and luxury. Nov-March $12,000/mo.; Apr $14,000; May $16,000; June $25,000; July $40,000; Aug $60,000; Sept $60,000. Permit# 0595.

Enjoy living in the crown jewel of Orient Village, the Shaw House built in 1730. Restored & meticulously maintained with original exposed beams, wide-plank floors, period hardware, 3 updated wood burning fireplaces, custom cabinetry & woodwork. 2 large decks span the back of the house overlooking Orient Harbor & Yacht Club. Offered June $15,000; July 1-20 $25,000; Sept $15,000. Permit #0293.

Enjoy a beautiful airy and bright mint condition Bay Front Orient Contemporary home, perfect for relaxing and entertaining. This 4-bedroom 4.5 bath home has gourmet kitchen, fireplace, open common space for easy entertaining. First floor has access to bay side screened porch from living room and den (or 4th bedroom with full bath). Second floor master bedroom and a guest bedroom open onto upper bay side deck, a third bedroom with full bath completes the layout. Private stairs to the beach and deeded beach rights to association Bay beach just a short walk from the house. Property is close to all village amenities: Country Store, Post Office, Marinas, Bay and Sound beaches. Offered Apr $10,000; May $12,000; June $15,000; July $35,000; Aug $35,000; Sept $20,000; Oct $15,000; Nov $10,000. Permit# 1020.

Impeccably restored 19th Century gem located in the heart of Orient Village with bay views. Close to bay and sound beaches, and a stroll to all village amenities. Featuring 2 parlors, 3 bedrooms, library, office, eat-in kitchen, updated baths, charming garden, out-door dining, and grill, out-door shower. Offered May $7,000; Aug 12-26 $10,000; Sept $10,000; Oct $7,000; Nov $6,000. Permit #0483.

Beautifully updated & fully renovated traditional Arts & Crafts home in the heart of Orient Village and one block from Orient Harbor. Gourmet kitchen with Thermador 6 burner/griddle stove, Subzero refrigerator, Bosch dishwasher. Enclosed front porch. Fenced yard, outdoor shower, backyard deck for relaxing, grilling & dining. Professionally landscaped with vegetable garden and outdoor shower. Offered April $9,000; May $10,000; June $16,000; July $25,000; Sept $16,000. Permit #0827.

Authentic 1770 Cottage in the heart of Orient Village. Lovingly restored & maintained Village home on beautifully landscaped lot, offering private grounds & distant views of sunsets over the bay. Furnished in period antiques, screened-in porch off kitchen, first floor bedroom. Walk to amenities, bay beach, Yacht Club, marina, farm stand & Jitney. Offered Sept $7,000. Permit #0091.

Stunning Waterfront shingle style home overlooking Long Island Sound. 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 Aug-LD $55,000; Sept 5-30 $25,000. Permit# 1108.

Enjoy this Waterfront rental just steps to Goose Creek beach. Easy water access to Goose Creek from this private location, perfect for kayaking and paddle boarding. Features include 3 bedrooms including second floor primary en-suite with water views, 2 additional guest bedrooms, 2 additional guest baths and plenty of living space overlooking Goose Creek. Spacious bright kitchen, dining area with doors to waterside deck where you will experience beautiful sunsets. The perfect retreat for your summer fun or any other time of the year. Close to all North Fork amenities. Permit # 1023