Shelter Island Holiday Packages

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Top Shelter Island holiday packages

Price found within the past 48 hours. Click for updated prices.
The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Manhattan
per person
2 Aug - 5 Aug
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
8.8/10 Excellent! (1,614 reviews)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
per person
2 Aug - 5 Aug
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
9.8/10 Exceptional! (1,199 reviews)
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
per person
2 Aug - 5 Aug
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
9/10 Wonderful! (2,115 reviews)
Everything about the INNSIDE was excellent, location, staff, cleanliness and ammenities.. would highly recommend

Reviewed on 1 Nov. 2022

The Lexington Hotel, Autograph Collection

The Lexington Hotel, Autograph Collection

4 out of 5
Manhattan
per person
2 Aug - 5 Aug
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
8.2/10 Very Good! (1,267 reviews)
Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Manhattan
per person
11 Aug - 14 Aug
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
9/10 Wonderful! (4,003 reviews)

Top Shelter Island hotels

Montauk Blue Hotel

Montauk Blue Hotel

2 out of 5
108 South Emerson Avenue, Montauk, NY
Book a stay at this beach hotel in Montauk. Enjoy free WiFi, a beach locale, and parking (surcharge). Popular attractions Montauk Point Lighthouse and Montauk ...
"Could not enter hotel unless you were 25 we were 21 but they let us stay thankfully and we had a wonderful experience. Expedia should include if there are any rules like that."

Reviewed on 13 Jun. 2025

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Montauk Blue Hotel
Montauk Yacht Club

Montauk Yacht Club

4 out of 5
32 Star Island Rd, Montauk, NY
Book a stay at this beach hotel in Montauk. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the property condition ...
"front desk was lovely !!"

Reviewed on 8 Jun. 2025

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Montauk Yacht Club
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Not bad
"The location was great- cute town. The room was clean and pretty basic. Beds could have been more comfy. Overall, it was fine given the amount paid."

Reviewed on 13 Jun. 2025

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Pier Blue Inn Old Saybrook - Essex
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.