Shelter Island Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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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.
La Quinta Inn & Suites by Wyndham Secaucus Meadowlands

La Quinta Inn & Suites by Wyndham Secaucus Meadowlands

3 out of 5
Save 100% on your flight
per person
Sep 19 - Sep 26
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
7/10 Good! (2,096 reviews)
Staff was friendly. Room was clean.

Reviewed on Jul. 12, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
per person
Aug 28 - Sep 4
found 12 hours ago
Roundtrip flight included
Montreal (YUL) to New York (JFK)
8.4/10 Very Good! (532 reviews)
Right on the water. Private beach with chair and umbrellas.they will serve you right on the beach bye getting you food and drinks also has a outdoor swimming pool..nice staff..nothing special about the continental breakfast..bagels, fruit, small croissants, small danish and some hard boiled eggs..coffee and oj..i was pleased with my stay. King deluxe room..small table with chairs on the shared deck..could sit outside til about 2pm and the sun starts to beat on you but no biggy..was very humid out when my wife and i was there..a/ c really could not cool the room as much as we would have liked. Nothing wrong with the a/c it just because the sun beating on the hotel all day..luckily i brought a couple of small usb fans to help keep cool at night while we slept did the trick..overall i enjoy my stay and you could not ask for anything more when it comes to the scenery..

Reviewed on Jul. 10, 2025

The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
Save 100% on your flight
per person
Aug 28 - Sep 4
found 12 hours ago
Roundtrip flight included
Montreal (YUL) to New York (JFK)
8.8/10 Excellent! (480 reviews)
This hotel is a pure gem. The service is fantastic, the front desk team works to make sure you are truly taken care of, including our dog. Very calm vibe, its super clean, quiet and perfect. Already looking at another couple of nights in August!

Reviewed on Jul. 11, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
per person
Sep 13 - Sep 16
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,006 reviews)
What a great place! The location was fantastic, the staff was great, and the views were unbelievable. Definitely want to come back some day!

Reviewed on Jul. 12, 2025

Night Hotel Broadway

Night Hotel Broadway

2.5 out of 5
Manhattan
Save 100% on your flight
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
7/10 Good! (2,169 reviews)
Bed was on the softer side but comfy. Room was spacious. Bathroom was clean and all of the most forgotten items were stocked in the bathroom. Staff was friendly.

Reviewed on Jul. 14, 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

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

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

Marram
Marram
4 out of 5
21 Oceanview Terrace, Montauk, NY
The price is CA $646 per night from Jul 16 to Jul 17
CA $646
CA $996 total
Jul 16 - Jul 17
includes taxes & fees
8.6/10 Excellent! (180 reviews)
"We loved our stay at Marram! The property is a little slice of beach magic. The location was absolutely perfect, and the private beach was exactly what we were hoping for. Tranquil and beautiful, they have effortlessly blended luxury into the unpretentious surf town vibes that Montauk is known for. ..."

Reviewed on Jul. 10, 2025

Marram
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 CA $151 per night from Aug 3 to Aug 4
CA $151
CA $174 total
Aug 3 - Aug 4
includes taxes & fees
7.6/10 Good! (1,008 reviews)
Excellent Place to Stay!!!...5 Stars & More!!
"We stayed 5 days! Customer service was great ;) Housekeeping was great, the cafe in the morning was excellent! Lounge area if you wanted to go out in the evening they had Pool, Darts, & Karaoke If you didn't want to go to the Beach, they had a Pool/Gym Right near the Highway & Route 1 We had a wonderful ..."

Reviewed on Jul. 10, 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 CA $683 per night from Jul 24 to Jul 25
CA $683
CA $781 total
Jul 24 - Jul 25
includes taxes & fees
9.2/10 Wonderful! (97 reviews)
"The hotel was very clean, updated and directly on the bach. Also all shops and restaurants are walkable."

Reviewed on Jul. 12, 2025

Montauk Blue Hotel
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

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

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

CA $218
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting

From Mattituck: North Fork Area Bike Tour with Food Tasting

CA $187
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
See all activities in Shelter Island

Frequently asked questions

How much does a Shelter Island vacation package cost?
Offering great value package deals from CA $698 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.