Shelter Island Holidays

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Shelter Island Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The William Vale

The William Vale

5 out of 5
Save 100% on your flight
per person
13 Jan - 19 Jan
found 10 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
8.6/10 Excellent! (1,000 reviews)
Clean and really nice

Reviewed on 15 Nov,2024

The Carlyle, A Rosewood Hotel

The Carlyle, A Rosewood Hotel

5 out of 5
Manhattan
Save 100% on your flight
per person
13 Jan - 19 Jan
found 10 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9.2/10 Wonderful! (717 reviews)
Always love staying in unique and historic properties, and the Carlyle is at the top of that list! Their customer service is top notch, and all of the staff went out of their way to make our stay special!

Reviewed on 15 Nov,2024

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Save 100% on your flight
per person
13 Jan - 19 Jan
found 10 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9.6/10 Exceptional! (39 reviews)
Boutique hotel atmosphere in the middle of Manhattan

Reviewed on 15 Nov,2024

The Manner

The Manner

5 out of 5
Manhattan
Save 100% on your flight
per person
13 Jan - 19 Jan
found 10 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
8/10 Very Good! (3 reviews)
The service is here is exceptional. The art of hospitality lives on here. From your first “hello” at the door - to all the small touches - the staff here are impeccable. It’s a great location. We will be back.

Reviewed on 30 Oct,2024

The New York EDITION

The New York EDITION

5 out of 5
Manhattan
per person
13 Jan - 19 Jan
found 10 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9/10 Wonderful! (414 reviews)
For the price I just cannot accept that you don’t get an in room coffee machine. They offer free coffee in lobby up to 10:30am, but I hate having to trek down first thing in the morning. Hat to also call to get shower gel as there were no extras in the room. Check in took 15 mins. Room was ok for the price. Service was good.

Reviewed on 20 Oct,2024

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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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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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 hotels in Silver Beach

Shelter Island Beach Holiday

There's nothing that can beat a Shelter Island holiday. Whether you're enjoying refreshing margaritas at a local hot spot or reading your favourite book by the ocean's edge, your trip to Shelter Island is the time to live out your beachy dreams. Many will suggest you stay close to Wades Beach, situated just 2 kilometres from downtown. However, you'll also discover a fantastic range of Shelter Island holiday deals around Menhadden Lane Beach and Shell Beach, two other well-liked nearby options.

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$118 per night from 8 Dec to 9 Dec
S$118
includes taxes & fees
8 Dec - 9 Dec
7.4/10 Good! (1,000 reviews)
"Kind staffs!"

Reviewed on 12 Nov,2024

Quality Inn Old Saybrook - Westbrook
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 S$107 per night from 24 Nov to 25 Nov
S$107
includes taxes & fees
24 Nov - 25 Nov
7.6/10 Good! (892 reviews)
"Everything was satisfactory"

Reviewed on 15 Nov,2024

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 S$482 per night from 5 Dec to 6 Dec
S$482
includes taxes & fees
5 Dec - 6 Dec
8.2/10 Very Good! (604 reviews)
"The staff was very friendly and the receptionist upgraded our room since the hotel was not as busy and it was wonderful."

Reviewed on 5 Nov,2024

Gurney's Montauk Resort & Seawater Spa
See all 4,670 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 S$2,674. 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.

Popular places to visit

Menhadden Lane Beach

Why not spend a care-free afternoon at Menhadden Lane Beach during your travels in Shelter Island Heights?

Menhadden Lane Beach

What to do in Shelter Island

The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

S$235
Per adult
76% of travellers recommend
The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC
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. 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.