Shelter Island Holidays from NZ$3,257

Book a Hotel + Flight or Car together to unlock savings

Choose two or more items and save on your trip:
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to NZ$545 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

The Latest Shelter Island Holiday Deals

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
per person
3 Jun - 9 Jun
Return flight included
Auckland (AKL) to New York (JFK)
9.8/10 Exceptional! (1,001 reviews)
Had a great stay! The room was quiet clean and nicely appointed. There was always staff at the front desk,- very welcoming and gracious. I would definitely stay there again

Reviewed on 19 Apr. 2024

Millennium Hilton New York One UN Plaza

Millennium Hilton New York One UN Plaza

4 out of 5
Manhattan
per person
3 Jun - 9 Jun
Return flight included
Auckland (AKL) to New York (JFK)
8/10 Very Good! (1,362 reviews)
We loved our stay at Hilton. It was definitely top notch accommodations. The city view is definitely worth the extra cost. The room was spacious and cozy and the bathroom was large with plenty of storage. The only unexpected charges I didn't like were the $300 security deposit which I'm assuming is $100/night. Most hotels are only $100 for your entire stay. Also they inform you of a "credit" for their restaurant, but don't inform you that you're getting charged whether you use this "credit" or not. The menu items were pricier than we would have expected to pay so we opted not to visit the restaurant at all. If I had known this credit was an actual charge then we would have at least made the cost worth it. The staff was super friendly and other than the constant maintenance on the middle elevator we really enjoyed our stay!

Reviewed on 13 Apr. 2024

Home2 Suites By Hilton New York Times Square

Home2 Suites By Hilton New York Times Square

3 out of 5
Manhattan
per person
3 Jun - 9 Jun
Return flight included
Auckland (AKL) to New York (JFK)
8.4/10 Very Good! (440 reviews)
Liked the location in Times Square. Very hard to get a table at breakfast. Dining area not big enough to accomodate everyone. Breakfast hours should be extended to 10:00 am.

Reviewed on 19 Apr. 2024

The Manhattan at Times Square Hotel

The Manhattan at Times Square Hotel

4 out of 5
Manhattan
per person
1 Jun - 8 Jun
Return direct flight included
Wellington (WLG) to New York (JFK)
5.6/10 (4,180 reviews)
They never pick up the phone. For the location they should look into updating the rooms. For the money the hotel is not up to par. A lot of potential. FRONT DESK NEVET ANSWERS THE PHONE

Reviewed on 19 Apr. 2024

Nesva Hotel

Nesva Hotel

2.5 out of 5
Queens
per person
1 Jun - 8 Jun
Return direct flight included
Wellington (WLG) to New York (JFK)
8.4/10 Very Good! (594 reviews)
Very nice and convenient hotel

Reviewed on 1 Mar. 2024

Prices and availability subject to change. Additional terms may apply.

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
Default Image

Silver Beach

While Silver Beach may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Sunset Beach and Shell Beach.

Find hotel + flight trips in Silver Beach

Our pick of the best Shelter Island Hotel Deals

Hyatt Place Long Island East End
Hyatt Place Long Island East End
3 out of 5
451 East Main Street, Riverhead, NY
Fully refundable
The price is NZ$259 per night from 25 Apr to 26 Apr
NZ$259
per night
25 Apr - 26 Apr
9/10 Wonderful! (997 reviews)
"did not like the parking situation. Did not like that they have a bar but no real bartender."

Reviewed on 15 Apr. 2024

Hyatt Place Long Island East End
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$772 per night from 25 Apr to 26 Apr
NZ$772
per night
25 Apr - 26 Apr
8.2/10 Very Good! (558 reviews)
"Very wonderful"

Reviewed on 17 Apr. 2024

Gurney's Montauk Resort & Seawater Spa
Montauk Manor
Montauk Manor
3.5 out of 5
236 Edgemere St., Montauk, NY
The price is NZ$260 per night from 22 Apr to 23 Apr
NZ$260
per night
22 Apr - 23 Apr
9/10 Wonderful! (996 reviews)
"Stunning & majestic, luv'd every moment there!"

Reviewed on 13 Apr. 2024

Montauk Manor
See all 4,737 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.

Frequently asked questions

How much does a Shelter Island holiday package cost?
From just NZ$3,257. Yes, you read that right. Our Shelter Island packages are the easiest way to stretch your budget. Combine your favourite flights, hotels and rental car and get out and see this vibrant destination.
How do I get a cheap travel package to Shelter Island?
Book everything all in one place with our Shelter Island holiday packages. We have deals on flights, hotels and more that’ll keep your pocketbook happy and your spirit of adventure alive. And, with more than 550 partner airlines and 1 000 000 properties globally to choose from, you’ll have endless opportunities to mix and match as you want.
What are the top hotels in Shelter Island?
People travelling to Shelter Island often book a room at Waterfront House With Dock And Private Beach or Stunning Waterfront Estate House With 270 Degree Sea Views On 7 Private Acres. You’ll find them in Silver Beach. Another great neighbourhood is Hay Beach. Recently Renovated Mid - Century Modern House In Shelter Island and Tranquil Resort Style Retreat With Luxury Gunite Pool 2 Min From Sandy Beaches are well-liked options in this part of town.
How far in advance should I book my Shelter Island holiday?
While prices do change, we generally recommend booking your flight as soon as possible. Many international airfares are available on Expedia up to 12 months in advance. If you’re booking last minute, you may still get lucky. Cheap journeys to Shelter Island sometimes appear only weeks before departure.
What does an Expedia Shelter Island travel package include?
Hotels, car rentals and flights — we bring you the very best deals. All you have to do is select your preferred combination. After you’ve made your booking, you can add on the exciting stuff like experiences and tours. Our travel packages make it easy to customize an awesome Shelter Island holiday.
What should I know before booking a Shelter Island travel package?
Our prices are always low. However, you’ll enjoy even more bargains when you book your hotels, flights and car rentals together. With an Expedia package, you’ll always get transparent pricing and loads of choice.
Can I choose my airline with a Shelter Island Expedia holiday package?
Yes — and it’s simple too. Expedia has access to more than 550 partner airlines all over the world. Our packages give you the freedom to pick from available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Shelter Island holiday package?
Yes you can, and we’re here to help. You may be able to cancel or amend your Shelter Island holiday package for free if you booked in the last 24 hours. But you may incur a fee from your hotel, airline or car rental company if you booked more than 24 hours ago. If your circumstances suddenly change, have a look at our Customer Service Portal for further information.

Discover the most popular places to visit in Shelter Island

Image for Shell Beach

Shell Beach

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

Shell Beach
Image for Gardiner's Bay Country Club

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
Image for Mashomack Preserve

Mashomack Preserve

Explore the great outdoors at Mashomack Preserve, a lovely green space in Shelter Island. Stroll along the beaches or discover the sunsets in this family-friendly area.

Mashomack Preserve

What to do in Shelter Island

Image for Private Hamptons Tour with Outlet Center Shopping

Private Hamptons Tour with Outlet Center Shopping

NZ$1,945
Per adult
Private Hamptons Tour with Outlet Center Shopping
See all activities in Shelter Island

More holiday ideas

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.