Accommodations in Shelter Island

5 out of 5 average rating, 10 reviews

All season island beach oasis - Hamptons area!

Heavenly island oasis, minutes by car to beach and town.Huge, sunny 4 bedroom home overlooking a pond and a sculpture garden in a park-like setting on a magically peaceful cul-de-sac. Hamptons without the headaches. Kawaii grand piano, fast WiFi. Cathedral entrance, 4 bedrooms, 2 1/2 bathrooms, separate living room, dining room, breakfast room with bay windows, huge deck. Perfect summer beach vacation. Check out the reviews for this beautiful retreat. Ferry ride to the Hamptons or Greenport.

An expansive outdoor area features a heated pool and hot tub, surrounded by lush greenery and tall trees. Lounge chairs with umbrellas are positioned nearby, set against a backdrop of vibrant grass and shaded by mature trees, creating a serene space for relaxation.

4.88 out of 5 average rating, 26 reviews

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**

The living area features warm wood paneling and ample natural light from large windows. A wood-burning stove is positioned beside a comfortable sofa, with a chandelier offering soft illumination. A coffee table sits centrally, with various seating options and artwork on display.

4.96 out of 5 average rating, 164 reviews

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

Guest suite in North Fork

A modern bathroom features a walk-in shower with a glass enclosure and white subway tiles. A double vanity with sleek storage sits opposite a toilet. Decorative photos are arranged on the dark wall above the vanity, while a light fixture illuminates the space. A rug lies on the floor.

4.91 out of 5 average rating, 315 reviews

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!

4.94 out of 5 average rating, 187 reviews

Home in North Fork

Harbor Heights

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

5 out of 5 average rating, 13 reviews

A wrap-around balcony provides sweeping views of Gardiner’s Bay. Comfortable lounge chairs are positioned for relaxation, while the clear sky reflects over the water. The area offers a serene setting for enjoying the outdoors.

Home in North Fork

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 ⛱

Cottage in Shelter Island

A spacious living area features large windows and skylights allowing natural light to fill the space. Contemporary sofas are arranged around a wooden coffee table, with a view of the outdoors showcasing trees and water. A dining table is visible in the background.

4.91 out of 5 average rating, 23 reviews

Waterfront Getaway on Shelter Island

This bright, spacious, private 3 bedroom, 2 bath contemporary home located at the end of the secluded Westmoreland peninsula on Shelter Island is the ideal retreat for summer. Hosting waterfront views from every room leading to a large open deck for gatherings of all kinds. This remote cottage is only 5 minutes from 2 of the best beaches on Shelter Island, Shell and Crescent Beach. Bring your water sports and enjoy Westneck creek and it’s beautiful scenic views!

Guesthouse in Shelter Island

A serene saltwater pool is framed by lush greenery and blooming flowers, enhancing the outdoor space. A hot tub is positioned alongside, inviting relaxation. The guest house is visible in the background, surrounded by trees and well-maintained landscaping.

5 out of 5 average rating, 64 reviews

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!

5 out of 5 average rating, 26 reviews

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.

Superhost

A fire pit is positioned on the sandy beach, with flames flickering brightly. The setting sun casts warm hues of orange and pink across the horizon, reflecting off the calm water, creating a serene atmosphere for evening gatherings.

4.9 out of 5 average rating, 116 reviews

Hay Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Cleaning fees for winter stays are 0$.

Home in Shelter Island Heights

4.95 out of 5 average rating, 40 reviews

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.

Apartment in Shelter Island Heights

A round wooden dining table is surrounded by four metal chairs. Natural light enters through two large windows, with framed black-and-white photographs arranged on the wall beside them. A decorative centerpiece is placed on the table, offering a rustic touch to the space.

4.91 out of 5 average rating, 247 reviews

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

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Other great vacation rentals in Shelter Island

A shaded seating area is presented under an orange canopy, featuring a wooden table surrounded by six deep blue cushioned chairs. It is set on a wooden deck, with the serene in-ground saltwater pool visible in the background, complemented by verdant gardens and vibrant plants.

4.89 out of 5 average rating, 9 reviews

Serenity on Shelter Island with a Pool & Hot tub

ChrisRating, 5 stars9 months ago

Mary Ann was a great host. Super responsive and provide excellent details and very helpful information. Her house is beautiful with a wonderful oasis in the back with pool, hot tub, and fire pit with plenty of space to lounge. Our family felt right at home and very comfortable. We hope to come back again.

Home in Shelter Island Heights

An outdoor mahogany deck features a circular dining table surrounded by four wicker chairs, with additional seating in the form of a loveseat. Two large umbrellas provide shade, and a gas grill is covered and positioned nearby. Lush greenery is visible in the background.

5 out of 5 average rating, 10 reviews

Laid Back Relaxation

SallieRating, 5 stars3 weeks ago

We really enjoyed Jared’s property. The light-filled living and dining room were spacious and comfortable, and the kitchen was modern and well-equipped. We would stay here again!

A serene waterfront scene captures gentle waves lapping against smooth rocks. The sky displays a captivating sunset with hues of orange, pink, and purple reflecting on the water's surface, creating a peaceful atmosphere at the day's end.

4.93 out of 5 average rating, 80 reviews

Family Friendly Island Home

LelandRating, 5 stars9 months ago

Bruno’s place was really quaint and nice. Bruno was easy to communicate with. Would recommend it again for sure!

A newly built house features a light-colored exterior with large, dark-framed windows. The entrance is highlighted by a small covered porch. Surrounding the home is a well-maintained lawn with neatly trimmed bushes lining the pathway, leading to a white gate on one side.

5 out of 5 average rating, 3 reviews

New vacation house on the island(new pool)

JamesRating, 5 stars9 months ago

Iwona was a terrific host. The home is immaculately maintained, with high ceilings and large windows looking over beautiful green space. It is a calming environment, both indoors and out. The location is convenient to the town center, a nature preserve, beaches, restaurants, and the north and south ferries. Based on our experience, we recommend highly!

A spacious estate is set against a twilight sky, with two separate dwellings visible amid well-manicured lawns. Large trees provide shade, while warm light glows from the windows, indicating a welcoming atmosphere. The serene surroundings emphasize the property's privacy and seclusion.

5 out of 5 average rating, 7 reviews

6-acre Hidden Estate for 10 w/FP, Pool, Chef's Kit

JaneRating, 5 stars2 weeks ago

Several of my family members stayed at Christine's house while on Shelter Island for a family wedding. The main house and cottage were both so beautiful and so comfortable and cozy. The grounds were positiviely idyllic including the tucked away, inviting pool. It truly felt like it could be our family's house. We all fell in love. The beds were comfortable with crisp white linens. When we weren't outside, the kitchen was a constant gathering place as was the sunroom and the dining room. I can't say anything about the TVs since we didn't turn one on once. Didn't even think about it - were having too much fun being together. Internet was great! Before arrival, Christian was a constant source of communication, making sure we were all set. Pay attention to his succinct instructions of how to get to the house. They are spot on. Kim, the manager, was there to greet us and let us in and answer any questions. She was so helpful. Going to SI? Stay at Christine's! You'll be glad you did!

Guesthouse in Shelter Island

A spacious outdoor seating area with a low, sectional sofa and a circular coffee table is set on a wooden dock. Two large umbrellas provide shade over the seating area, while the surrounding greenery reflects in the calm water of Menantic Creek.

4.89 out of 5 average rating, 9 reviews

Stylish Studio Suite on Shelter Island

AnnaRating, 5 stars10 months ago

Kate’s place was perfect—down a quiet and private road but close to everything Shelter Island has to offer. The apartment was cozy and comfortable with all the necessities. Kate was very responsive when needed but you also have privacy. Lovely stay—I hope to come again!

The living area features large glass doors that open to a view of trees and distant water. A light grey rug anchors two chairs and a sectional sofa, while a small circular coffee table holds a chess set. A television is mounted on the wall.

Apartment in Shelter Island

5 out of 5 average rating, 15 reviews

Modern Waterview Apartment in Silver Beach

MarkRating, 5 stars3 weeks ago

We really enjoyed our stay at Ena and Robs well appointed quiet apartment on shelter Island. It was in a great location close to beaches and in a perfect spot to bike around the island. Everything in the apartment was of a high quality, spotlessly clean including the comfortable bed and the linens, the kitchen was well equipped, the shower very nice and there was a lovely little balcony to sit and have your coffee in the morning. The host were very friendly and open. We would definitely go back!

A life-sized chess set occupies the vibrant green lawn, with large white and black pieces arranged strategically on a stone pathway. The modern wooden house features dark siding and a bright yellow door, offering a welcoming contrast. A cozy chair and a sculptural element add to the inviting outdoor space.