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.
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Price was CA $1,617, price is now CA $1,017 per person
CA $1,017
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
7.6/10 Good! (3,805 reviews)
Clean and room big enough. No microwave and refrigerator

Reviewed on Oct 28, 2026

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Save 100% on your flight
Price was CA $6,819, price is now CA $4,245 per person
CA $4,245
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to New York (JFK)
9.2/10 Wonderful! (713 reviews)

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was CA $4,919, price is now CA $3,202 per person
CA $3,202
per person
Dec 2 - Dec 5
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)

Hotel Beacon

Hotel Beacon

4 out of 5
Manhattan
Save 100% on your flight
Price was CA $2,370, price is now CA $1,545 per person
CA $1,545
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (1,536 reviews)

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Save 100% on your flight
Price was CA $3,968, price is now CA $2,615 per person
CA $2,615
per person
Jan 11 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)
We had an incredible stay at the Essex House last week with our two kids (one is 7 and the other turned 4 on our trip). We booked the king suite, thinking that even though it's NYC and the room will likely be small, it would be the best option for a family of 4. We were SHOCKED at the size of the suite! Not only was it enough room for all of us, it was downright roomy! We had plenty of space for our stay. The amenities and cleanliness of the hotel are superior, room service was delicious (if expensive), and best of all...the guest relations team sent a special surprise gift to our room for our 4 year olds birthday. They sent him balloons, two pieces of cake, and a bag full of stuffies and goodies. He was THRILLED and we were so touched by the thoughtfulness. Both of our kids have already asked if - not only can we go back to New York - but can we stay at the Essex House again! The location was incredible and overall the Essex House played a big part in how wonderful and effortless our trip was. Already looking at dates in the Spring to visit again! Thank you Essex House and your wonderful staff!

Reviewed on Oct 19, 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 beach with a wooden sign that reads "Please take off your shoes!"

Menantic Creek

If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Wades Beach and Shelter Island Historical Society.

Find hotels in Menantic Creek

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

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 $520 per night from Nov 16 to Nov 17
CA $520
CA $713 total
Nov 16 - Nov 17
includes taxes & fees
8.2/10 Very good! (875 reviews)
"Restaurant was excellent . Rooms needed repairs and resort fee should have been waived for broke room items"

Reviewed on Oct 26, 2026

Gurney's Montauk Resort & Seawater Spa
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 $251 per night from Nov 1 to Nov 2
CA $251
CA $313 total
Nov 1 - Nov 2
includes taxes & fees
Water's Edge Resort & Spa
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 $115 per night from Nov 15 to Nov 16
CA $115
CA $132 total
Nov 15 - Nov 16
includes taxes & fees
8/10 Very good! (1,000 reviews)
"The room had a musty smell when we entered and didn't resemble in the least how it was presented on the website. The room looked dirty, pillows looked old and stained yellow. The television didn't work. The shower barely had any pressure. The employees were very nice."

Reviewed on Oct 27, 2026

Pier Blue Inn Old Saybrook - Essex
See all 4,617 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 close-up of a beach with various shells and pebbles.

Shell Beach

10.0/10 (1 review)
Why not spend a carefree afternoon at Shell 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 $1,017 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.

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