Shelter Island Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Shelter Island Vacation

Lock in a Shelter Island vacation package that includes everything you need and nothing you don't. Great for views, fishing and nature, consider basing yourself in the neighborhood of Orient Point. If taking in sights is on the cards during your trip to Shelter Island, check out top attractions like 67 Steps Beach, Railroad Museum of Long Island and Kontokosta Winery. Whatever your travel plans or the size of your budget, organizing a tailored Shelter Island vacation is a cinch with Expedia.

Top Shelter Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was CA $1,555, price is now CA $902 per person
CA $902
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (2,498 reviews)
Cute hotel

Reviewed on Jul 16, 2026

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Price was CA $3,670, price is now CA $2,181 per person
CA $2,181
per person
Oct 1 - Oct 4
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.2/10 Wonderful! (685 reviews)
Great location, great view

Reviewed on Jul 5, 2026

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was CA $2,272, price is now CA $1,370 per person
CA $1,370
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (1,617 reviews)
Amazing stay! The rooftop has magical views of the city. The staff is great, very welcoming and asked us where we were from and if it’s our first time visiting NYC. The room was excellent with great cable tv and clean towels. Comfortable bed and pillows. Completely satisfied with our stay here , definitely will be coming back!

Reviewed on Jul 15, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $5,115, price is now CA $3,183 per person
CA $3,183
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,006 reviews)

EVEN Hotel Brooklyn by IHG

EVEN Hotel Brooklyn by IHG

4 out of 5
Price was CA $1,585, price is now CA $1,002 per person
CA $1,002
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,932 reviews)
We recently stayed here for a last minute weekend getaway, and it exceeded all our expectations. From the moment we walked through the doors the lobby smell and decor was welcoming. And the flavored water was an excellent touch. ​The front desk team was incredibly welcoming and managed to check us in early without any hassle. Every staff member we encountered—from Housekeeping was friendly, professional, and genuinely seemed to care about our experience. Our room was clean and beautifully designed. The bed was incredibly comfortable (we slept like babies!).

Reviewed on Jul 14, 2026

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
A calm river with a boat docked on the right bank, surrounded by lush greenery and trees.

Silver Beach

While Silver Beach might 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 Wades Beach.

Find hotels in Silver Beach

Shelter Island Beach Vacation

There's nothing like a Shelter Island vacation 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.

Ready to book your vacation to Shelter Island?

 

Choose your dates

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 refundable
The price is CA $129 per night from Jul 23 to Jul 24
CA $129
CA $148 total
Jul 23 - Jul 24
includes taxes & fees
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 CA $1,418 per night from Aug 17 to Aug 18
CA $1,418
CA $1,944 total
Aug 17 - Aug 18
includes taxes & fees
8.4/10 Very good! (827 reviews)
"The rooms need to be updated to meet the hotel standards."

Reviewed on Jul 16, 2026

Gurney's Montauk Resort & Seawater Spa
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
The price is CA $651 per night from Aug 6 to Aug 7
CA $651
CA $771 total
Aug 6 - Aug 7
includes taxes & fees
9.2/10 Wonderful! (1,365 reviews)
"Rooms and facilty were clean and room was reasonably spacious. Comfortable bed. Nice kitchenette and balcony. Breakfast in b the restaurant was good. Outdoor pool very nice and heated. Close to most areas of interest. Shuttle available but we did not use."

Reviewed on Jul 9, 2026

Montauk Manor
See all 4,713 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Shelter Island attractions

A clear blue sea with a wooden pier extending into the water, a sailboat in the distance, and a person standing in the water.

Wades Beach

10.0/10 (1 review)
Why not spend a carefree afternoon at Wades Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.
See properties

Frequently asked questions

How much does a Shelter Island vacation package cost?
Offering great value package deals from CA $902 on Expedia, you'll be thrilled with how little a vacation to Shelter Island costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Shelter Island?
The off-season is the best time to visit Shelter Island if you're trying to keep costs down. Another tip for getting cheap Shelter Island vacation packages? Avoid visiting during public holidays and any major festivals or events.
How many days is enough for Shelter Island?
To get the most out of your Shelter Island vacation, we suggest staying for 5 days. Split your time between discovering Greenport Carousel, Bay Street Theatre and other top attractions, as well as experiencing neighbourhoods like Greenport West and The Heights. If you've got some spare time, add a tour or day trip to your Shelter Island vacation itinerary.
Is it worth booking a vacation package to Shelter Island?
It's no wonder a Shelter Island vacation is on the must-do list of many travellers. Well-known attractions like Shell Beach are just the beginning of what you can explore here.
How to find the best Shelter Island package deals?
Start your search for a Shelter Island package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Shelter Island package deal right away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Shelter Island adventure off to a flying start.
Is it cheaper to book a Shelter Island vacation as a package?
You can enjoy significant savings on your next Shelter Island break by booking a personalized vacation package. Click on the "Package" heading, then enter your travel dates and destination to browse the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Shelter Island?
If you're considering a spontaneous Shelter Island adventure, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land amazing deals on your flights and hotels by booking well in advance.
How to plan a trip to Shelter Island?

  1. Choose the perfect time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit Shelter Island.
  2. Budget wisely: On top of the cost of your accommodations, you should factor in other expenses. These include flights, transportation and food. Also, put aside some extra funds for unexpected expenses that may come up during your trip to Shelter Island.
  3. Decide how long to go away for: Now that you're up to speed on Shelter Island, you can figure out the perfect length of your vacation. Pull together a rough itinerary and give yourself enough time for all the things you want to do.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to choose a Shelter Island vacation package that brings all your bookings together.

Explore a world of travel with Expedia

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