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: <a href="/property/work-and-play-special-extended-stay-discount/HA-3211443742" class="class="static-page-link"">Work and Play Special! Extended Stay Discount</a> <a href="/property/peaceful-and-private-shelter-island-getaway/HA-3211116587" class="class="static-page-link"">Peaceful and Private Shelter Island Getaway</a> <a href="/property/farmhouse-nestled-by-meadow-pool-near-beaches-and-centrally-located/HA-3211523409" class="class="static-page-link"">Farmhouse Nestled by Meadow, Pool, Near Beaches and Centrally Located!</a> <a href="/property/private-oasis-with-new-baths-and-heated-gunite-pool-near-wades-beach/HA-3211050826" class="class="static-page-link"">Private oasis with new baths and heated Gunite pool near Wades Beach</a> <a href="/property/tranquility-base-architect-renovated-modern-ranch-with-heated-pool/HA-3211212991" class="class="static-page-link"">Tranquility Base; Architect-Renovated, Modern Ranch With Heated Pool</a> <a href="/property/private-wooded-summer-house-5-minute-walk-to-wades-beach/HA-321553290" class="class="static-page-link"">Private wooded summer house 5 minute walk to Wades Beach</a> <a href="/property/waterfront-house-with-dock-and-private-beach/HA-1213594708" class="class="static-page-link"">Waterfront House With Dock And Private Beach</a> <a href="/property/lovely-home-by-the-sea-with-dock-and-heated-gunite-pool/HA-321425548" class="class="static-page-link"">Lovely home by the sea with dock and heated Gunite pool!</a> <a href="/property/contemporary-home-with-heated-pool-and-waterviews-on-shelter-island/HA-121989574" class="class="static-page-link"">Contemporary Home with heated pool and waterviews on Shelter Island</a> <a href="/property/shelter-island-sun-filled-modern-waterfront-home-with-dock/HA-1214327666" class="class="static-page-link"">Shelter Island Sun Filled Modern Waterfront Home with Dock</a>

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

The average cost for a cottage rental in Shelter Island is $481 per night. Toodoo 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: Charming, Historic Cottage Charming, Renovated Island Cottage - Shelter Island License #: 012-2017 650 YARDS TO SUNSET BEACH ! Waterfront House With Dock And Private Beach Shelter Island Retreat with Outdoor Pool! The Pridwin Hotel Work and Play Special! Extended Stay Discount <a href="/all/usa/new-york/shelter-island" class="class="static-page-link"">See all pet-friendly vacation rentals in Shelter Island on Toodoo</a>

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 Toodoo shows that there are Over 3 private swimming pools or cottages with indoor pools in the Shelter Island area along with other great amenities.

Shelter Island Cottage Rentals By Owner

From US $752

10.0 (4 Reviews)

Cottage

Charming, Historic Cottage

Air Conditioner
View
Ocean View

Shelter Island Cottage Rentals & Holiday Homes

Find the best cottages in Shelter Island - We found 3 exact matches

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