Shelter Island Holidays from NZ$3,378

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The Latest Shelter Island Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Price was NZ$4,436, price is now NZ$3,378 per person
NZ$3,378
per person
20 Aug - 26 Aug
found 23 hours ago
Return flight included
Auckland (AKL) to Newark Liberty Intl. Airport (EWR)
7.4/10 Good! (3,217 reviews)
Parking is expensive. As a whole it is a nice and affordable hotel and close to everything

Reviewed on 27 June 2026

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Price was NZ$8,089, price is now NZ$5,594 per person
NZ$5,594
per person
20 Aug - 26 Aug
found 23 hours ago
Return flight included
Auckland (AKL) to New York (JFK)
9.6/10 Exceptional! (235 reviews)
Great staff, great room with personalized touches, great food at restaurants, small gym and no spa on site. Fabulous hotel, would return!

Reviewed on 20 June 2026

Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was NZ$4,740, price is now NZ$3,626 per person
NZ$3,626
per person
20 Aug - 26 Aug
found 23 hours ago
Return flight included
Auckland (AKL) to New York (JFK)
8.8/10 Excellent! (7,502 reviews)
On a hot summer’s day, the window AC unit did a heroic job keeping us cool.

Reviewed on 27 June 2026

The Prince Kitano New York

The Prince Kitano New York

4.5 out of 5
Manhattan
Price was NZ$5,011, price is now NZ$3,850 per person
NZ$3,850
per person
20 Aug - 26 Aug
found 23 hours ago
Return flight included
Auckland (AKL) to New York (JFK)
9.4/10 Exceptional! (2,292 reviews)
Great location. Quiet clean lovely hotel

Reviewed on 25 June 2026

San Carlos Hotel

San Carlos Hotel

4.5 out of 5
Manhattan
Price was NZ$4,852, price is now NZ$3,739 per person
NZ$3,739
per person
20 Aug - 26 Aug
found 23 hours ago
Return flight included
Auckland (AKL) to New York (JFK)
9.4/10 Exceptional! (1,831 reviews)
This was our 2nd time staying at the San Carlos as didn’t disappoint. Location perfect for walking to Central Park, Grand Central. Located near subway station. Room was very spacious, clean with tv & air con. Staff very pleasant and helpful.

Reviewed on 22 June 2026

Our guide on where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island
A beach with a wooden sign that reads "Please take off your shoes!"

Menantic Creek

While there might not be top attractions in Menantic Creek, you can explore the larger area and discover places like Wades Beach and Sunset Beach.

Find hotels in Menantic Creek

Shelter Island Holiday

Shelter Island Beach Holiday

There's nothing like a Shelter Island holiday to give you a little extra bounce in your step. The sound of rolling surf and the smell of clean ocean air are sure to refresh your mind, body and soul. To be close to the town centre on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometres away). If you're planning to stay for a bit, look into our Shelter Island packages. Not only can you save some cash, you'll also have other amazing beaches near you to explore, like Shell Beach and Menhadden Lane Beach.

Our pick of the best Shelter Island Hotel Deals

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
The price is NZ$2,743 per night from 15 July to 16 July
NZ$2,743
15 July - 16 July
includes taxes & fees
8.4/10 Very good! (814 reviews)
"Great experience."

Reviewed on 25 June 2026

Gurney's Montauk Resort & Seawater Spa
Offshore Montauk

Offshore Montauk

4 out of 5
71 S Emerson Ave Montauk NY
The price is NZ$1,550 per night from 20 July to 21 July
NZ$1,550
20 July - 21 July
includes taxes & fees
9.2/10 Wonderful! (144 reviews)
"We had a great stay"

Reviewed on 25 June 2026

Offshore Montauk
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$182 per night from 7 July to 8 July
NZ$182
7 July - 8 July
includes taxes & fees
8/10 Very good! (1,002 reviews)
"staff and parking"

Reviewed on 22 June 2026

Pier Blue Inn Old Saybrook - Essex
See all 4,741 properties in Shelter Island
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.

Stay near popular Shelter Island attractions

A clear blue sea with a wooden pier extending into the water, a sailboat in the distance, and a person standing in the water.

Wades Beach

10.0/5 (1 review)
Wades Beach offers calm, shallow waters and a broad sandy shoreline perfect for families seeking safe swimming. Lifeguards patrol in summer, and the pavilion provides a comfortable spot to enjoy the tranquil setting.
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