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Shelter Island house rentals

We found 2,252 house rentals — enter your dates for availability

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

Are there any holiday home rentals in Shelter Island?
Stay in one of our 2,252 holiday home rentals in Shelter Island and you'll have the ideal base for your next big adventure. Menantic Creek, Coecles Harbour and The Heights are among the city's most popular areas.
How much does it cost to stay in a holiday rental house in Shelter Island?
Your dream holiday home rental in Shelter Island is waiting to be discovered, with a range of prices from budget-friendly accommodation to more upscale options. Enter your travel dates to compare, ensuring you find the right place for you and your crew.
When is the best time to rent a holiday house in Shelter Island?
First, decide whether you prefer the bustle of high season or the quieter vibe of low season. Also think about things like seasonal weather conditions and what you'd like to see in Shelter Island. Whenever you go, there'll be a holiday home rental with your name on it.
Where can I rent a Shelter Island holiday house with great views?
There's only one thing better than enjoying a break in one of our Shelter Island holiday home rentals — staying someplace that comes with gorgeous views. Scroll through our options to discover a house with the amenities you need and the outlooks that'll make your getaway even more memorable. Sort your results by "Guest rating" or "Recommended" and see what's available.
Does Shelter Island have any weekend house rentals?
Some of our holiday houses are available for weekend rental, making them perfect for spontaneous getaways. Enter your desired travel dates to view the availability. You may need to play around with dates and have a little flexibility in your plans to find the right holiday home rental in Shelter Island.
Are there any pet-friendly house rentals in Shelter Island?
Embark on your next adventure with your four-legged friend at one of our 15 pet-friendly holiday home rentals in Shelter Island. These properties come with features that'll make your dog feel at home, such as a fenced-in yard to play in. Just check the "Pets allowed" filter to find a house that has space for every cherished member of your family.
What are the top things to do in Shelter Island?
East Hampton Main Beach, Orient Point County Park and 67 Steps Beach are terrific attractions that'll keep the whole crew occupied in Shelter Island. There's nothing like a getaway to bring everyone together, so check out our holiday home rentals in this exciting destination.
Why should I book my holiday rental house with Stayz?
We take the hassle out of finding your ideal holiday home rental. Use our filters to fine-tune your search by budget, property type, amenities and more. Whatever your preference, you'll always get the whole space for you and whoever you're adventuring with. Plus, our cancellation policies offer peace of mind should your plans change. You'll get a full refund if you cancel your booking within the timeframe specified by the property's cancellation policy.