Shelter Island Holidays from NZ$2,795

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The Latest Shelter Island Holiday Deals

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

The Gallivant Times Square

3.5 out of 5
Manhattan
Price was NZ$3,404, price is now NZ$2,795 per person
NZ$2,795
per person
8 Nov - 15 Nov
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
6.4/10 (918 reviews)
Very close to Times Square

Reviewed on 23 Sept 2025

Romer Hell's Kitchen

Romer Hell's Kitchen

4 out of 5
Manhattan
Price was NZ$4,586, price is now NZ$3,685 per person
NZ$3,685
per person
8 Nov - 15 Nov
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
9.4/10 Exceptional! (2,040 reviews)
Had a slight hiccup on our arrival but staff was very friendly and helpful. Walkable and transportation access to most everything we had planned. So much fun!

Reviewed on 23 Sept 2025

Interfaith 21

Interfaith 21

2 out of 5
Manhattan
Price was NZ$3,632, price is now NZ$2,933 per person
NZ$2,933
per person
8 Nov - 15 Nov
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
8.6/10 Excellent! (20 reviews)
Small room but very clean

Reviewed on 13 Aug 2025

Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
Price was NZ$3,936, price is now NZ$3,192 per person
NZ$3,192
per person
8 Nov - 15 Nov
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
8/10 Very Good! (2,177 reviews)
I book 2 Queen premier rooms with balcony’s. It stated on your web site that they were 487 square feet. But when we arrived and checked in the rooms were very small. At least half the size of what it stated online. I went to the front desk and asked why. She said she didn’t know what it stated online and I booked thru a 3rd party site , I would have to take it up with them . If we wanted a bigger room they had one available for an extra $20.00 a night. So we just paid the extra to get the size of room we originally wanted. I thought it was a Nate and switch. I was not happy. I think you either need to up date your site or speak to Hotel 32 32.

Reviewed on 20 Sept 2025

Candlewood Suites New York City-Times Square by IHG

Candlewood Suites New York City-Times Square by IHG

2.5 out of 5
Manhattan
Price was NZ$4,181, price is now NZ$3,392 per person
NZ$3,392
per person
8 Nov - 15 Nov
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
8.4/10 Very Good! (1,496 reviews)
Close to everywhere especially to the drop off uber shuttle if you take one

Reviewed on 24 Sept 2025

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
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Menantic Creek

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

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
The price is NZ$157 per night from 25 Sept to 26 Sept
NZ$157
25 Sept - 26 Sept
includes taxes & fees
7.8/10 Good! (1,010 reviews)
"Highly recommend!"

Reviewed on 21 Sept 2025

Pier Blue Inn Old Saybrook - Essex
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$927 per night from 28 Sept to 29 Sept
NZ$927
28 Sept - 29 Sept
includes taxes & fees
8.2/10 Very Good! (667 reviews)
"Amazing resort, very friendly staff, food and drinks are Amazing! We enjoyed our stay."

Reviewed on 15 Sept 2025

Gurney's Montauk Resort & Seawater Spa
Montauk Blue Hotel

Montauk Blue Hotel

2 out of 5
108 South Emerson Avenue, Montauk, NY
The price is NZ$341 per night from 9 Oct to 10 Oct
NZ$341
9 Oct - 10 Oct
includes taxes & fees
9/10 Wonderful! (140 reviews)
"It is right on the ocean so you can either enjoy the beach or relax on chairs right outside your door and watch the waves. Staff was very friendly and accomodating. As far as physical structure, there was a chunk of wood missing from the railing outside our room and there were ants in the room. Also, ..."

Reviewed on 19 Sept 2025

Montauk Blue Hotel
See all 4,720 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.

Discover the most popular places to visit in Shelter Island

Gardiner's Bay Country Club

Enjoy a round of golf in Shelter Island at Gardiner's Bay Country Club. Stroll along the area's waterfront or simply enjoy its wineries.

Gardiner's Bay Country Club

Wades Beach

Why not spend a care-free afternoon at Wades Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.

Wades Beach

Shelter Island Historical Society

You can spend time browsing the exhibits at Shelter Island Historical Society during your trip to Shelter Island. Stroll along the beaches or experience the area's museums.

Shelter Island Historical Society

What to do in Shelter Island

Join a small group full-day wine tour with a certified Sommelier host

Long Island Wine and Food Day Trip with Sommelier host from NYC

NZ$251
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting

From Mattituck: North Fork Area Bike Tour with Food Tasting

NZ$235
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
See all activities in Shelter Island
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.