Alojamientos vacacionales en Shelter Island

Newly Renovated w/ Pool, Hot tub & Fireplace

Shelter Island Rental License #: 2025-L-0056 !!!PLEASE DO NOT PUT IN A BOOKING REQUEST UNTIL WE HAVE HAD A CONVERSATION VIA THIS SITE. THANK YOU!!!! Great for fall and winter! Perfect for families! 4 Adults Max. Newly renovated, light filled home! Heated pool and hot tub in summer in a private tree-filled yard. Fireplace and great sledding in the colder months. Mid-century modern style; close to Shelter Island Heights and beaches. **POOL & HOT TUB CLOSED MID OCTOBER UNTIL MAY**

Shelter island retreat

Two bedroom on the top floor of a house on Shelter Island on secluded one-acre. fire pit, wood-burning fireplace, layered decks, stainless steel kitchen, five minutes to beach. close to the south ferry .outdoor sauna and hot tub. Own entrance very private. owner lives on property as well in very separate space. 19W-0009 Own entrance very private. owner lives on premise as well in very separate space.has cat that lives in studio with owner 19W-0009 Long term rental also Available

The Greenport Suite—private entry + near the beach

Welcome to The Greenport Suite! With its separate entrance, secluded outdoor patio space and ideal location, this newly-redesigned private suite in our contemporary Village home is perfect for enjoying a North Fork getaway. We are located just a few short blocks from bay beaches, the harbor, and public transport, while the area's celebrated wineries are a short drive or bike ride away. Come see why Forbes named Greenport one of the 11 prettiest villages in the United States!

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

★ "Beautiful hidden home on the water… enjoy the North Fork summer in style." Private beachfront property with 2 homes & views of Gardiner’s bay. ☞ Bikes + kayaks + paddle boards ☞ Wrap around balcony w/ seating ☞ Fully equipped + stocked kitchen ☞ Deck w/ lounging + water views ☞ Dedicated workspace + printer ☞ Master w/ king + bathroom ☞ 55” Smart TV + Xbox ☞ Indoor gas fireplace 6 mins → DT Greenport (cafes, dining, shopping) 13 mins → Orient Beach State Park ⛱

Bayfront 1BR/2BR detached guesthouse with pool

Perfect relaxing getaway for a couple or family. Bayfront 1BR/2BR fully detached guest house with gorgeous morning views. Property has saltwater pool + hot tub (open May -October) and bay access via private dock. Central to both north & south forks (wineries + Hamptons or Montauk just short drive away). Down the road from famous Shelter Island Sunset Beach + golf course. Come explore the beauty of the Hamptons without the stress!

Hamptons - Shelter Island Farmhouse

Kid friendly! Perfect two family split! Come enjoy our island retreat. Relax with the whole family at this peaceful pad. You will be 2 min on bike from Wades Beach. You can also walk to the best BBQ/seafood in Shelter, Commander Codys. Features a large open kitchen/dining room plus also a spacious living room. 4 bedrooms with new mattresses, huge outdoor patio for family BBQs. No dogs please.

Silver Beach, 3 Bedroom cottage w/ pool

Enjoy summer on Shelter Island in this 3 bedroom, 2 bathroom, freshly painted and well equipped MCM ranch house on 3/4 of an acre. Located at the end of a private road, it's in walking distance to Shell Beach, town landings and a beautiful sunset viewing spot. Brand new, heated, inground pool w/ color changing light, central air, deck, fire pit and BBQ make this a great vacation home.

Walk to Vineyards, Beaches, Farms & Town

Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!

Squire Chase House

Wide open loft like space in the heart of the Heights walking distance to North ferry and Marie Eiffel market Many antiques including 1930s leather club chairs and a wonderful 1850 Swedish gustavian sofa in the living room many original pieces of art work Note :the bath tub in the master bedroom is for decoration only Shelter Island license B Zone