Accommodations in Shelter Island

4.92 out of 5 average rating, 140 reviews

Condo in North Fork

Beachside Waterview 2Br Condo w/ Pool in Greenport

Relax in a pristine 2Br condo with ocean & pool views. Our remodeled apartment is part of high-end development nestled on LI Sound, just minutes from downtown Greenport. Sip a glass of wine while watching sunset, catch some rays on the beach or deep in the pool. 2 bedroom condo with ocean view, beach, and pool (seasonal) Comfortably sleeps 6 Private beach access year-around Pool (seasonal) Functional kitchenette 2 bathrooms, all toiletries Linens and towels are provided Smart TV AC/Heat

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

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 spacious living area is highlighted by large windows that provide expansive views of the water. A light wood ceiling adds warmth to the room. A modern sofa, accented by pillows, sits beside a round coffee table. A cozy armchair complements the seating arrangement.

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

There's a 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.

Guest suite in North Fork

A sandy path lined with tall grass leads to a serene beach. The gentle waves of the ocean can be seen in the distance under a clear blue sky, inviting a peaceful atmosphere.

4.88 out of 5 average rating, 665 reviews

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!

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

A spacious covered deck features comfortable wooden seating arrangements overlooking a serene water view. Light wooden beams and flooring create a warm ambiance, while various cushions add texture. The scene is enhanced by a soft area rug and natural surroundings, inviting relaxation.

5 out of 5 average rating, 13 reviews

Waterfront Treehouse with Pool as seen on HBO

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

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

A modern cabin is seen with black wooden siding and large glass doors. Soft lighting fixtures are mounted on either side, illuminating the entrance. Surrounding greenery includes potted plants and a bush, with a rustic dining area visible nearby.

5 out of 5 average rating, 5 reviews

Designer Renovated Farmhouse with Pool

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

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