Shelter Island cottage rentals

We found 105 cottage rentals — enter your dates for availability
Select from 87 homes, 10 cottages and other holiday rentals in Shelter Island to find one that's perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a fireplace. No matter what you're looking for, you'll be able to choose a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

Explore Shelter Island cottage rentals

Image of North Fork Resort

North Fork Resort

Sleeps 4 · 1 bedroom
9.6 out of 10
exceptional
(70 reviews)
More information about North Fork Resort, opens in a new tab

Top rated cottage rentals - Shelter Island

Backyard
Lovely place right on a lake
10.0 out of 10, Exceptional, 89 reviews
"Loved this place. It was so nice to lie in bed and hear the ducks and swans talk to each other. Plus so close to the beach! The kitchen was well equipped and easy to use. Lots of modern conveniences to make you feel comfortable."
Jess L.
Jess L.
Stayed Feb 2022
Private Coastal Two Bedroom Cottage on the Water

  • 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

How much does it cost to stay in a cottage rental in Shelter Island?

Where you stay, when you want to travel and the length of your escape will determine how much you pay for a cottage rental in Shelter Island. Key in your travel details on Stayz to compare your options and then select one that's right for you.

When is the best time to rent a cottage in Shelter Island?

To lock in your ideal cottage rental in Shelter Island, timing plays a big part. Book early and you'll have a wider range of cottages to choose from, especially if you're travelling during peak tourist periods. You can usually find cheaper prices or special early booking discounts.

Where can I rent a Shelter Island holiday cottage with great views?

When looking for your cottage rental in Shelter Island, make use of our "Location" filter. This lets you narrow down the sorts of areas you want to stay in, whether that's around nature or somewhere close to the action.

Does Shelter Island have any lakeside cottages?

Wake up to gorgeous vistas every morning and fall asleep to the peaceful sounds of nature at night in one of Stayz's lakeside cottage rentals. Add some outdoor adventures in the daytime and you've got yourself the perfect holiday by the water. To find out if there are any lakeside cottages in Shelter Island, make use of our "Location" filter and then select "Lake."

What are the top things to do in Shelter Island?

Organise a few excursions from your cottage rental, making sure to include East Hampton Main Beach, Orient Point County Park and 67 Steps Beach. These well-known Shelter Island sights are family friendly, so everyone can come along.

Why should I book my holiday cottage with Stayz?

Stayz offers customer support from booking until the end of your trip, so every aspect of your holiday is worry-free. Plus we think our cottage rentals are something special — think amenity-packed stays ideal for families and delightfully rustic options that are suited to a romantic break. When you book with us, you can also take advantage of flexible cancellation policies and other benefits like payment and deposit protection.