Shelter Island Holiday Packages

Save when you book Shelter Island package deals

Choose two or more items and save on your trip:

Top Shelter Island holiday packages

Price found within the past 48 hours. Click for updated prices.
OYO Times Square

OYO Times Square

4 out of 5
Manhattan
Price was NZ$5,710, price is now NZ$4,412 per person
NZ$4,412
per person
5 Sept - 13 Sept
found 17 hours ago
Return flight included
Auckland (AKL) to New York (JFK)
6.8/10 (2,014 reviews)

San Carlos Hotel

San Carlos Hotel

4.5 out of 5
Manhattan
Price was NZ$7,721, price is now NZ$5,394 per person
NZ$5,394
per person
5 Sept - 13 Sept
found 17 hours ago
Return flight included
Auckland (AKL) to New York (JFK)
9.4/10 Exceptional! (1,834 reviews)
Great location. Nice size suite. Will return.

Reviewed on 30 July 2026

Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
Price was NZ$6,147, price is now NZ$4,530 per person
NZ$4,530
per person
5 Sept - 13 Sept
found 17 hours ago
Return flight included
Auckland (AKL) to New York (JFK)
8/10 Very good! (2,499 reviews)

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was NZ$7,220, price is now NZ$5,353 per person
NZ$5,353
per person
5 Sept - 13 Sept
found 17 hours ago
Return flight included
Auckland (AKL) to New York (JFK)
9.8/10 Exceptional! (1,623 reviews)
Great location. Cool place. Decent size rooms. Great value. The staff is awesome. Andrew and Morgan were specifically amazing. This is my new crash pad in NYC.

Reviewed on 30 July 2026

The Hotel @ Fifth Avenue

The Hotel @ Fifth Avenue

3.5 out of 5
Manhattan
Price was NZ$5,914, price is now NZ$4,719 per person
NZ$4,719
per person
5 Sept - 13 Sept
found 17 hours ago
Return flight included
Auckland (AKL) to New York (JFK)
8.2/10 Very good! (2,102 reviews)
Very comfortable room with all what you need for your staying

Reviewed on 29 July 2026

Top Shelter Island hotels

Montauk Yacht Club

Montauk Yacht Club

4.5 out of 5
32 Star Island Rd Montauk NY
The price is NZ$1,330 per night from 31 Aug to 1 Sept
NZ$1,330
31 Aug - 1 Sept
includes taxes & fees
Stay at this luxury hotel in Montauk. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the helpful staff and the property condition in their ...
"Great service! Especially the wait staff"

Reviewed on 28 July 2026

Opens in a new windowMontauk Yacht Club
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is NZ$826 per night from 18 Aug to 19 Aug
NZ$826
18 Aug - 19 Aug
includes taxes & fees
Stay at this beach hotel in Greenport. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
"My family and I recently stayed at the Sound View Hotel and had a wonderful experience all thanks to their front desk staffer named Adrianne. While our trip was off to a rough start regarding the initial room we were assigned, the moment I voiced my complaints to Adrianne she stepped in and went ..."

Reviewed on 29 July 2026

Opens in a new windowSound View Greenport
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundable
The price is NZ$203 per night from 6 Aug to 7 Aug
NZ$203
6 Aug - 7 Aug
includes taxes & fees
Stay at this hotel in Old Saybrook. Enjoy free Wi-Fi, free parking and a picnic area. Our guests praise the helpful staff and the clean rooms in their reviews. ...
"Not the most updated place. It was good for one one night."

Reviewed on 30 July 2026

Opens in a new windowPier Blue Inn Old Saybrook - Essex
Don't see what you're looking for?
See all available properties in Shelter Island
View all properties
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.

More Destinations