Shelter Island Trip

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    Save up to ₹43,962 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top Shelter Island Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Hotel @ Fifth Avenue

The Hotel @ Fifth Avenue

3.5 out of 5
Manhattan
per person
21 Sept - 24 Sept
found 11 hours ago
Return direct flight included
Delhi (DEL) to New York (JFK)
8.2/10 Very Good! (1,653 reviews)
The hotel has very small rooms

Reviewed on 19 Jun 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
per person
21 Sept - 24 Sept
found 11 hours ago
Return direct flight included
Delhi (DEL) to New York (JFK)
9.8/10 Exceptional! (1,212 reviews)
Very neat hotel! Great to stay at travel!

Reviewed on 23 Jun 2025

Millennium Hotel Broadway Times Square

Millennium Hotel Broadway Times Square

4 out of 5
Manhattan
per person
21 Sept - 24 Sept
found 11 hours ago
Return direct flight included
Delhi (DEL) to New York (JFK)
7.6/10 Good! (5,366 reviews)
Friendly staff and continent location.

Reviewed on 25 Jun 2025

Aura Hotel Times Square

Aura Hotel Times Square

4 out of 5
Manhattan
per person
21 Sept - 24 Sept
found 11 hours ago
Return direct flight included
Delhi (DEL) to New York (JFK)
8.6/10 Excellent! (2,056 reviews)
Great location, clean rooms. The gym is kept clean, but 1 of the 2 treadmills wasn't working. Property is renovated and there are tons of things to do in the vicinity. Super walkable and accessible.

Reviewed on 26 Jun 2025

Royalton New York

Royalton New York

4 out of 5
Manhattan
per person
21 Sept - 24 Sept
found 11 hours ago
Return direct flight included
Delhi (DEL) to New York (JFK)
7.8/10 Good! (1,001 reviews)
The lobby area was beautiful, the rooms had old carpet

Reviewed on 25 Apr 2025

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 Shell Beach.

Find hotels in Menantic Creek

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.

Top hotels in Shelter Island

Montauk Yacht Club
Montauk Yacht Club
4 out of 5
32 Star Island Rd, Montauk, NY
8.4/10 Very Good! (1,002 reviews)
"Gorgeous stay on a girls trip"

Reviewed on 21 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
The price is ₹6,457 per night from 29 Jun to 30 Jun
₹6,457
₹7,425 total
29 Jun - 30 Jun
includes taxes & fees
7.6/10 Good! (981 reviews)
"This is a great place to stay with an outstanding location in Old Saybrook right on RT 1. Great breakfast cafe right across the street."

Reviewed on 24 Jun 2025

Pier Blue Inn Old Saybrook - Essex
Montauk Blue Hotel
Montauk Blue Hotel
2 out of 5
108 South Emerson Avenue, Montauk, NY
The price is ₹34,861 per night from 30 Jun to 1 Jul
₹34,861
₹39,828 total
30 Jun - 1 Jul
includes taxes & fees
9.2/10 Wonderful! (80 reviews)
"T"

Reviewed on 25 Jun 2025

Montauk Blue Hotel
See all 4,803 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?
Offering excellent value package deals from ₹123,352 on Expedia, you'll be surprised at how little a holiday to Shelter Island costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Shelter Island?
To pick up cheap Shelter Island holiday packages, plan your trip outside of peak periods like public holidays and major festivals. You'll typically find better availability and lower prices for flights and hotels.
How many days is enough for Shelter Island?
We recommend booking a Shelter Island holiday for at least 5 days. This will give you time to visit major attractions such as Menhadden Lane Beach and Havens House, and also check out neighbourhoods like Greenport West and The Heights. You might even be able to squeeze in a day trip outside of Shelter Island.
Is it worth booking a holiday package to Shelter Island?
It's easy to see why a Shelter Island holiday is on the to-do list of many travellers. Leading attractions like Shell Beach are just the start of things to keep you busy here.
How to find the best Shelter Island package deals?
Bagging a cheap Shelter Island package deal is a breeze with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, apply a few filters and browse what's available. You can tweak your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most affordable Shelter Island package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Shelter Island holiday as a package?
You can enjoy significant savings on your next Shelter Island getaway by booking a customised holiday package. Click on the "Package" heading, then enter your travel dates and destination to view the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Shelter Island?
Land amazing discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Shelter Island getaway.
How to plan a trip to Shelter Island?

  1. Pick your travel dates: What you'd like to do in Shelter Island and your favourite season will help you decide when to get away.
  2. Figure out your budget: Ensure you have enough money to cover everything from dining out and transportation to activities and airfares. Your accommodation will likely be the largest expense during your trip to Shelter Island.
  3. Decide how many days away: Start by making a list of all the activities and sights you'd like to experience in Shelter Island. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your airfare and accommodation: After you've settled on your travel dates and duration, lock in the perfect Shelter Island holiday package for you.

Popular places to visit

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