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Shelter Island Holiday Packages

Sunset
...the beach
Dering Harbor
Shelter Island Holiday Packages
Want to book a holiday to Shelter Island? Whether you're off for a romantic holiday, family trip, or an all-inclusive holiday, Shelter Island holiday packages on TripAdvisor make planning your trip simple and affordable.
Find the perfect holiday package for Shelter Island on TripAdvisor by comparing Shelter Island hotel and flight prices. Travellers like you have written 1,069 reviews and posted 683 candid photos for Shelter Island hotels. Book your Shelter Island holiday today!
Or build your own Shelter Island holiday package
Shelter Island House
#1 Hotel in Shelter Island
Shelter Island House
This place was much better than expected. I booked without ever visiting Shelter Island and reading a few negative reviews and went with my gut based on positive reviews and...
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Dering Harbor Inn
#2 Hotel in Shelter Island
Dering Harbor Inn
“fun” 27/08/2017
Beautiful hotel the rooms are hugIe. Very clean great service, great gym and best location. I wouldn't stay anywhere else. Studio was exceptionally large. Barbara is the best...
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The Pridwin Hotel
#3 Hotel in Shelter Island
The Pridwin Hotel
We stayed here last summer and LOVED it!!! After receiving an email announcing end of summer rates we decided to go back and visit the Pridwin again. The Pridwin is now one of my...
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2. Find the right flight
Cheap Flights to Shelter Island
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†  Prices are based on round trip travel with returns between 1-21 days after departure. These are the best fares found by travellers who searched TripAdvisor and a select group of our fare search partners in the past 72 hours. Ticket prices and seat availability change rapidly and cannot be guaranteed.