Luxury properties for rent Shelter Island, United States

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.

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.

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.

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.

2024 RATES: JUNE $12,500, JULY $16,000.00 AUGUST $17,000 MD-LD $44,500. Victorian classic in the heart of Greenport Village. Centrally located to all forms of public transportation and close proximity to public Bay beach. This property offers convenience, style and stunning views of Shelter Island and the Peconic Bay. Main features are large front porch, inviting/well appointed living spaces multiple en-suite bedrooms and a large rear yard for entertaining. This historical treasure has been recently updated and provides both the charm of a classic New England port village home and the accommodations of an updated home. Easy North Fork living in Greenport Village.

Magical 1840's Cottage in Browns Hills with endless views across Orient Bay. Beautiful south facing garden abutting farm fields. Three bedrooms 1.5 baths, outdoor shower, deeded sound beach. A private, tranquil natural sanctuary in bucolic Orient. Offered July $15,000; Aug $15,000; Sept $8,000; year-round, furnished starting Sept $32,000/mo. Permit #0308.

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.

Available 2024- MD-LD $53,500, May $6,000, June $12,500, July $19,500, July-August $41,000, August-LD $21,500, September $8,000, October $6,000: Escape to sweeping dunes along the Long Island Sound in the Hamlet of Peconic. This restored 1940's beach cottage offers charm, character, modern amenities and easy summer water-front living. The grounds are sprawling, incredibly private, will offer breath taking sunset and the ideal setting for summer stargazing. The interior features 3 bedrooms, 2 bathrooms, 2 living rooms and updated bathrooms and kitchen. Enjoy this serene setting nestled away along some of the North Fork's most desirable beach fronts.