67 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 $25 to $26000 a night.

Information about Shelter Island

Vacation Rentals in Shelter Island

Find the best Shelter Island vacation rentals with Tripping.com. Choose from 1165 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $25 a night to $26000 a night.

Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 908 of homes in Shelter Island offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 520 rentals with pool or jacuzzi, or relax with the family in one of the 921 homes with cable TV.

For all those dog lovers and cat lovers, Shelter Island offers 435 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

Search properties from 11 rental sites in Shelter Island where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 874 HomeAway rentals, 130 TripAdvisor short term rentals and 92 Booking.com vacation rentals.
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