Shelter Island Vacation Packages

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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.
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
Jun. 19 - Jun. 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (2,786 reviews)
In the middle of everything! Great place with excellent staff, can’t wait to come back!

Reviewed on Apr. 29, 2025

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Save 100% on your flight
per person
Jun. 12 - Jun. 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (76 reviews)
This property was one of nicest small hotels we have ever stayed at. You didn’t want to even leave the room!!!

Reviewed on Apr. 21, 2025

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
Jun. 19 - Jun. 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (3,632 reviews)
Hotel meraviglioso, centralissimo, nuovo, ottima colazione e personale super gentile. Un’ottima scoperta. Se dovessimo tornare, soggiorneremo sicuramente lì.

Reviewed on Apr. 28, 2025

The Manner in the Unbound Collection by Hyatt

The Manner in the Unbound Collection by Hyatt

5 out of 5
Manhattan
Save 100% on your flight
per person
Jun. 12 - Jun. 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (24 reviews)
Beautiful hotel! Everyone who works there goes out of their way to make you feel welcome and special! Loved the “Library”. After I got over the initial shock of no TV in the room, I embraced it and it was perfect. Fantastic location for food and shopping. I will definitely be back!! Michi was a fantastic addition!!

Reviewed on Mar. 3, 2025

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Save 100% on your flight
per person
Jun. 19 - Jun. 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (606 reviews)
We loved our stay at the Lotte Towers! The rooms were very spacious for our family of 4. We were provided a fridge on request. The views were amazing. The lifts were quick to get us to the 58th floor! Our rooms were serviced twice daily. Cannot fault anything at Lotte would love to return one day!!

Reviewed on Apr. 15, 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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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 Crescent Beach and Sunset Beach.

Find hotels in Silver Beach

Shelter Island Beach Vacation

There's nothing like a Shelter Island vacation to put a spring in your step. The soothing sounds of rolling surf and the smell of salty sea air will rejuvenate your mind and body. To be close to the centre of town on your trip to Shelter Island, find a hotel around Shell Beach (only 3 kilometres away). If you plan to hang around a while, consider securing one of our Shelter Island vacation packages. Not only will you save some money, you'll also have other incredible beaches near you to explore, like Wades Beach and Menhadden Lane Beach. Now that's a win-win!

Ready to book your vacation to Shelter Island?

 

Choose your dates

Shelter Island Hotel Deals

Montauk Yacht Club
Montauk Yacht Club
4 out of 5
32 Star Island Rd, Montauk, NY
The price is CA $358 per night from May 4 to May 5
CA $358
CA $409 total
includes taxes & fees
May 4 - May 5
8.4/10 Very Good! (999 reviews)
"The staff was kind and very hospitable. Very beautiful environment and clean place to stay."

Reviewed on Apr. 29, 2025

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 CA $123 per night from May 5 to May 6
CA $123
CA $141 total
includes taxes & fees
May 5 - May 6
7.6/10 Good! (950 reviews)
"Convenient, great value"

Reviewed on Apr. 27, 2025

Pier Blue Inn Old Saybrook - Essex
Water's Edge Resort & Spa
Water's Edge Resort & Spa
3.5 out of 5
1525 Boston Post Road, Westbrook, CT
Fully refundableReserve now, pay when you stay
The price is CA $269 per night from May 4 to May 5
CA $269
CA $334 total
includes taxes & fees
May 4 - May 5
8.6/10 Excellent! (1,002 reviews)
"we had a room with a balcony that looked out to the ocean. terrific view. lovely property & staff was very friendly"

Reviewed on Apr. 22, 2025

Water's Edge Resort & Spa
See all 4,711 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

Frequently asked questions

How much does a Shelter Island vacation package cost?
Offering great value package deals from CA $1,206 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.

Discover the most popular places to visit in Shelter Island

Havens House

You can spend an afternoon browsing the exhibits at Havens House during your trip to Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.

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