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Shelter Island Cottage Rentals & Holiday Homes

Find the best cottages in Shelter Island - We found 9 exact matches

About Shelter Island Cottage Rentals on Holiday In The Hamptons

Searching for cottages to rent near Shelter Island? Holiday In The Hamptons features more than 9 cottages that are perfect for your next trip. Discover luxury cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Shelter Island have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. Holiday In The Hamptons’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Shelter Island.

Are you planning to travel to the lakeside, beach, or mountain area? Holiday In The Hamptons’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.

Holiday In The Hamptons boasts of 9 holiday cottages and places to stay in Shelter Island. The site provides unique Airbnb, VRBO, Holiday In The Hamptons-style cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget.

Frequently Asked Questions About Shelter Island Cottage Rentals

What are the top rated Cottage Rentals in Shelter Island?

There are a lot of options in Shelter Island. If you plan on staying in the Shelter Island area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Shelter Island:

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

The average cost for a cottage rental in Shelter Island is $568 per night. Holidayinthehamptons has a wide list of great cottages near Shelter Island that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Shelter Island that allow pets?

Yes, here are the top cottage rentals in Shelter Island that allow you to bring your pet:

See all pet-friendly vacation rentals in Shelter Island on Holidayinthehamptons

Do you have any rental cottages in Shelter Island that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Shelter Island to find one that works for you.

Are there quality cottages in Shelter Island that have indoor swimming pools?

As of 2026, the data from Holidayinthehamptons shows that there are Over 9 private swimming pools or cottages with indoor pools in the Shelter Island area along with other great amenities.