Alojamientos vacacionales en Shelter Island Heights

Mid-Century Gem with Pool. Steps to Private Beach.

Escape to our stylish mid-century modern retreat on Shelter Island. A 1 minute walk to stunning Crab Creek and a private neighborhood association beach, our home boasts 3 bedrooms, 2.5 baths and an outdoor shower, and sits on nearly an acre of secluded land. The backyard is a private oasis with towering trees, a bamboo forest and a large pool surrounded by beautiful landscaping. Enjoy an indoor fireplace in winter, an outdoor fireplace and grill in summer, or a beach bonfire under the stars.

Bungalow by the Bay

SMOKE FREE • ALLERGY FREE Rates Include a 15.5% AirBB Service Fee Early Check In & Late Check Out Bungalow by the Bay is an Inhabitable Work of Art, recrafted by owner architects. The design is inspired by all of the beauty of coastal living, incorporating organic and natural elements and environmentally conscious technology, to create a happy and healthy living space. Bungalow by the Bay is ideal for those who love sunrises, nature, water, fine wine, delicious food and dreamy sunsets.

De los mejores en Favorito entre huéspedes

Favorito entre huéspedes

Private Hay Beach Retreat with Heated Pool

Built in 2015, this airy 4-bedroom house sits on a private acre near Hay Beach and comes with a heated 16x38 gunite pool, well-equipped kitchen, gas grill and modern amenities. Contemporary furniture, uncluttered space; home office with a wired internet connection. Pool is open between 5/23/26 and 9/30/2026. Pricing inclusive of weekly cleaning, pool, yard, and garbage collection services as well as utilities. *Propane for pool heating charged separately for stays a week or longer*

De los mejores en Favorito entre huéspedes

Favorito entre huéspedes

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**

North Fork Sound Front Home with Pool

This Long Island Sound front property on nearly three acres of land with an inground, custom designed, gunite pool is the perfect vacation home. Walk down the ramp to your private beach for a kayak, paddle board or swim in the summer and enjoy a luxurious outdoor shower afterwards. In the fall and winter months, enjoy the extensive book collection and stay cozy by the fireplaces. Spacious and bright, this home has a unique aesthetic and can accommodate 8 guests comfortably.

Hay Beach Family Home: Fire Pit, Playroom, Yard

Two blocks from Hay Beach, this family-and-dog-friendly 3BR sleeps 6 in a quiet Shelter Island neighborhood. Fenced yard, fire pit, playroom, crib, toddler toys, beach gear, and bikes included. The home was built for families: open living area with wood-burning fireplace, full kitchen, 2 full baths, basement playroom, and workout space. Outside: fully fenced yard, fire pit, sun loungers, propane grill, Big Green Egg. Winter stays: $0 cleaning fee Nov–Mar.

De los mejores en Favorito entre huéspedes

Favorito entre huéspedes

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.

De los mejores en Favorito entre huéspedes

Favorito entre huéspedes

Laid Back Relaxation

Kick back and relax in this calm, stylish space. Nice newly updated home on a quiet street within walking distance to beaches, restaurants and a golf course. Great location near Shelter Island heights town, Crescent beach and Sunset beach. The location provides both privacy and relaxation at home with just a short walk or ride to popular Shelter Island spots.

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

De los mejores en Favorito entre huéspedes

Favorito entre huéspedes

Cosy North Fork Cottage with large backyard

Peaceful cottage with a huge double lot backyard. Park your car and never need to get in it again! Walk into town and walk to beaches! Our home features fire-pit seating area and outdoor heated shower and beach bikes. Enjoy the fabulous restaurants which are right on your doorstep at this charming little cottage.

De los mejores en Favorito entre huéspedes

Favorito entre huéspedes

Private Suite in a Greenport Historical Townhouse

Enjoy the Greenport experience at this centrally located, renovated Victorian home. Our place is a few minutes walk into town, where there is a flourishing restaurant and food scene. Lots of shops, cafes to explore too and beaches are a 15 minute walk. Take a boat tour of the harbor from nearby Preston's Dock.