78 Shelter Island Holiday Rentals

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Compare Shelter Island holiday rentals from 11 rental sites including HomeAway, TripAdvisor, Booking.com and more, ranging from $70 to $9920 a night.

Information about Shelter Island

Vacation Rentals in Shelter Island

Save hundreds with a Tripping.com vacation rental and forget about the expensive hotel room. For the ultimate getaway trip, Shelter Island offers 1570 vacation home rentals for an affordable price to match your budget and accommodation needs. Book one now for an average price of $887 a night, or a long-term rental for an average price of $27211 a month.

These homes offer a range of amenities, giving you more bang for your buck. For those looking to stay in a corporate rental, 1305 of Shelter Island’s rentals offer high speed internet so you can easily keep in touch with your company or team. Go for a swim at one of the 810 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 1233 cozy homes.

Traveling with pets? Choose from 567 pet-friendly rentals in Shelter Island for a quality experience. Tripping.com’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your furry buddy. Book instantly with properties marked “Instabook”, and check out our other listings now to find the perfect vacation home for you.

Search properties from 11 rental sites in Shelter Island where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 1286 HomeAway rentals, 160 TripAdvisor short term rentals and 52 Booking.com vacation rentals.