Shelter Island Holidays

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Shelter Island Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Manhattan
per person
13 Aug - 16 Aug
found 22 hours ago
Return flight included
Singapore (SIN) to New York (JFK)
8.8/10 Excellent! (1,626 reviews)
The room was clean when we arrived, The maids were not the best, we had to request more towels and they were great about bringing them. But we asked if they could remove the others and dirty dishes- they never did. Nor did they remove dirty cups nor did they replenish coffee. We only stayed a few nights, when we requested they didn't respond.

Reviewed on 10 Jul, 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
per person
13 Aug - 16 Aug
found 22 hours ago
Return flight included
Singapore (SIN) to New York (JFK)
9.8/10 Exceptional! (1,232 reviews)
Clean rooms. Friendly staff. Excellent area if you are a family with kids.

Reviewed on 9 Jul, 2025

The Lexington Hotel, Autograph Collection

The Lexington Hotel, Autograph Collection

4 out of 5
Manhattan
per person
13 Aug - 16 Aug
found 22 hours ago
Return flight included
Singapore (SIN) to New York (JFK)
8.2/10 Very Good! (1,275 reviews)
Very friendly and helpful staff, towels changed and trash removed daily! Clean environment! Very well located! We loved

Reviewed on 10 Jul, 2025

Hilton Club The Quin New York

Hilton Club The Quin New York

5 out of 5
Manhattan
per person
13 Aug - 16 Aug
found 22 hours ago
Return flight included
Singapore (SIN) to New York (JFK)
9.4/10 Exceptional! (1,074 reviews)
Nice rooms, quiet, and excellent location

Reviewed on 10 Jul, 2025

Hard Rock Hotel New York

Hard Rock Hotel New York

4.5 out of 5
Manhattan
per person
13 Aug - 16 Aug
found 22 hours ago
Return flight included
Singapore (SIN) to New York (JFK)
9.4/10 Exceptional! (4,612 reviews)
Location location location 2 mins walk to Times Square couldn’t have been happier rooms were spacious and ticked all the boxes. Would stay there again

Reviewed on 10 Jul, 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 Shelter Island Historical Society and Sunset 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

Quality Inn Old Saybrook - Westbrook
Quality Inn Old Saybrook - Westbrook
2.5 out of 5
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is S$163 per night from 3 Aug to 4 Aug
S$163
3 Aug - 4 Aug
includes taxes & fees
7.6/10 Good! (1,005 reviews)
"Very satisfied"

Reviewed on 9 Jul, 2025

Quality Inn Old Saybrook - Westbrook
Montauk Blue Hotel
Montauk Blue Hotel
2 out of 5
108 South Emerson Avenue, Montauk, NY
The price is S$627 per night from 13 Jul to 14 Jul
S$627
13 Jul - 14 Jul
includes taxes & fees
9.2/10 Wonderful! (95 reviews)
Ocean front room
"Stayed in an ocean front room. Everything about this hotel was nice except the room didn’t seem very clean upon arrival. Hair in the shower, the bathroom counter top didn’t look like it was wiped down, finger prints on the mirror, dirt stains on the skirt of the bed. Only other complaint is the upkeep ..."

Reviewed on 9 Jul, 2025

Montauk Blue Hotel
Montauk Yacht Club
Montauk Yacht Club
4 out of 5
32 Star Island Rd, Montauk, NY
8.4/10 Very Good! (1,005 reviews)
"Excellent"

Reviewed on 10 Jul, 2025

Get rates
Montauk Yacht Club
See all 4,796 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.

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

S$203
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
Half Day Private Long Island Wine Tour Experience

Half-Day Private Long Island Wine Tour Experience

S$371
per adult
Half-Day Private Long Island Wine Tour Experience
Vetted Flights and food pairings at local winery.

Long Island North Fork Sights Bites & Flights, Half-Day Tour: AM

S$433
per adult
Long Island North Fork Sights Bites & Flights, Half-Day Tour: AM
See all activities in Shelter Island

Frequently asked questions

How much does a Shelter Island holiday package cost?
Offering excellent value package deals from S$2,101 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.