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.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was CA $882, price is now CA $560 per person
CA $560
per person
Oct 7 - Oct 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
This place is the bomb. Loved our suite, loved the pool and the breakfast was wonderful

Reviewed on Aug. 12, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $4,002, price is now CA $2,370 per person
CA $2,370
per person
Oct 31 - Nov 3
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,009 reviews)
Wonderful room and staff. The Brooklyn Bridge view was amazing.

Reviewed on Aug. 21, 2025

Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Price was CA $1,404, price is now CA $895 per person
CA $895
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (6,263 reviews)
This is a reasonably priced hotel right in Times Square. It could not be more convenient for travelers who have come to see Broadway shows. It's an older building with small rooms but well-maintained.

Reviewed on Aug. 21, 2025

YO1 Longevity & Health Resorts, Catskills

YO1 Longevity & Health Resorts, Catskills

4 out of 5
Price was CA $1,921, price is now CA $1,229 per person
CA $1,229
per person
Sep 26 - Oct 1
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
8/10 Very Good! (469 reviews)
Will definitely be back and want to give a special shout out to Brandon. She was super helpful and very pleasant. Most importantly, my wife loved it and wants to go back…

Reviewed on Aug. 17, 2025

Hotel Beacon

Hotel Beacon

4 out of 5
Manhattan
Price was CA $2,601, price is now CA $1,666 per person
CA $1,666
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (1,269 reviews)
Clean room. Comfortable bed. Staff is great. Went to show next door. Easy comfortable trip. Cafe next door was delicious.

Reviewed on Aug. 17, 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 Sunset Beach and Crescent 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?

 

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Shelter Island Hotel Deals

The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39, Southampton, NY
The price is CA $224 per night from Sep 21 to Sep 22
CA $224
CA $291 total
Sep 21 - Sep 22
includes taxes & fees
7/10 Good! (913 reviews)
"Nice place. Recommend."

Reviewed on Aug. 18, 2025

The Atlantic Hotel
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 $140 per night from Sep 15 to Sep 16
CA $140
CA $161 total
Sep 15 - Sep 16
includes taxes & fees
7.6/10 Good! (1,011 reviews)
"Perfect spot for my visit"

Reviewed on Aug. 17, 2025

Quality Inn Old Saybrook - Westbrook
Marram

Marram

4 out of 5
21 Oceanview Terrace, Montauk, NY
The price is CA $405 per night from Sep 15 to Sep 16
CA $405
CA $725 total
Sep 15 - Sep 16
includes taxes & fees
8.6/10 Excellent! (213 reviews)
"Small, but comfortable room. Excellent location right on the beach. There was a mix up with our dinner at the hotel one night and my husband’s dinner came out much later than mine. It wasn’t a big deal, but the hotel comped our meal, brought us a free dessert, and comped our post-dinner drinks at ..."

Reviewed on Aug. 19, 2025

Marram
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
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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 $204
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 $191
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 $560 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.