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.

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 $16,000. 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.

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.

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.

Private, recently renovated, arts and crafts style ranch located in the heart of Orient Village. Three bedrooms, 2 full baths, open kitchen/ living room/ dining room, library, front porch, rear deck with screened outdoor dining area & grilling station. Close to beaches, marinas & village amenities. Offered Aug $15,000. Permit #0505.

Beautifully converted 19th C Barn - three story residence with 4 bedrooms, 3 full baths, Eat-in kitchen, deck off living room with sound views, and private beach access. Apr $5,000; May $5,000; June $8,000; July $15,000; Aug $15,000; Sept $10,000; Oct - Mar $4,000/mo; yearly $6,500/mo. Permit# 0774.

Vineyard Views. Modern Farmhouse on private 1 acre located on the only private, working vineyard in Orient Village. 16 x 32 heated pool, newly renovated chef's kitchen and baths. The home features 3 bedrooms, 3 full baths. Ground floor designed with open common space and designer furnishings for luxurious entertaining, featuring living room with cathedral ceiling with sliders to pool and deck, eat-in kitchen and dining room with sliders to vineyard deck. Den with pull out queen bed, bedroom with queen bed, 2 full baths, laundry and screened porch complete the ground floor plan. Second floor has 2 additional bedrooms; master with king bed, and 3rd bedroom with 2 full beds, and full bath. Amenities include central air, fully stocked kitchen with Aga stove, high speed internet, TVs with streaming video, gas grill. Walk to Village, Yacht Club & steps to a Willow Terrace bay beach. Embrace the North Fork lifestyle. Permit #0516

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 July $10,000; Aug $10,000; Sept $7,000. Permit #0091.

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

Charming exquisitely restored mission style cottage with unique privacy. Original beach stone fireplace, custom woodwork throughout, large deck, screened porch, 2 ensuite bedrooms, studio / office, gourmet kitchen and period furnishings. Walk to 2 beautiful sound beaches. July $15,000; Aug $15,000; Aug-LD $17,000. Permit# 1003.

Contemporary private, secluded home in bucolic Browns Hill, Orient. 12 x 25 heated/saltwater/gunite pool with deck & patio overlooking farm fields with distant bay view. A welcoming space from the foyer to the living room with wood burning fireplace, updated gourmet kitchen and dining room with panoramic farm and bay views. Three levels of living space with one bedroom & full bath on each floor: lower-level bedroom with deck, ground floor master ensuite bedroom with full bath and deck, second floor loft/bedroom. Wrap around deck and outdoor shower. Association Sound beach, just a short walk. Offered Feb 1 - March 18 $7,500; July $30,000; Aug $30,000. All inclusive. Permit # 0174.