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 Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

Manhattan
CA $1,256
per person
Oct 23 - Oct 26
found 2 days ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (3,936 reviews)
Air conditionné. Ne peut pas être contrôlé fait un bruit comme si vous êtes dans un avion Il fait froid dans la chambre et ils n’ont pu rien faire l’hôtel a reconnu qu’ils avaient un problème avec

Reviewed on Sep 3, 2026

Hotel Beacon

Hotel Beacon

Manhattan
CA $1,798
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (1,511 reviews)
Seven Beach Lane

Seven Beach Lane

CA $1,587
per person
Oct 4 - Oct 10
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.4/10 Exceptional! (33 reviews)
A great experience all around. The property, the rooms, and the super friendly staff made for a great stay. L

Reviewed on Sep 3, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

CA $2,168
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,013 reviews)
Absolutely beautiful😍

Reviewed on Sep 2, 2026

Sound View Greenport

Sound View Greenport

CA $1,331
per person
Nov 14 - Nov 21
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.4/10 Very good! (698 reviews)
I booked thru Expedia but never checked in because you were SOLD OUzt! Expedia has a problem to fix!

Reviewed on Sep 2, 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 Shelter Island Historical Society and Sunset Beach.

Find hotels in Menantic Creek
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 Crescent Beach and Sunset Beach.

Find hotels in Silver Beach
A pebble beach with calm water, a distant bridge, and a forested island.

Coecles Harbor

When in Coecles Harbor, you can plan a visit to Shelter Island Historical Society and Mashomack Preserve, some noteworthy sights in the nearby area.

Find hotels in Coecles Harbor
A calm lake with reflections of clouds, surrounded by trees and a distant structure.

Hay Beach

Hay Beach might not have many top sights, but Greenport Carousel and Greenport Harbor Brewing Company are two attractions nearby that you can check out.

Find hotels in Hay Beach
An aerial view of a large estate surrounded by water, featuring a prominent mansion, rocky shorelines, and a small island with a lighthouse.

Shorewood

While there might not be top attractions in Shorewood, you can explore the larger area and discover places like Mashomack Preserve and Shelter Island Historical Society.

Find hotels in Shorewood

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

Sound View Greenport

Sound View Greenport

58775 County Rd 48 Greenport NY
CA $324
CA $410 total
Oct 1 - Oct 2
includes taxes & fees
8.4/10 Very good! (712 reviews)
"I booked thru Expedia but never checked in because you were SOLD OUzt! Expedia has a problem to fix!"

Reviewed on Sep 2, 2026

Sound View Greenport
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
CA $127
CA $146 total
Sep 9 - Sep 10
includes taxes & fees
8/10 Very good! (1,000 reviews)
"Reasonable price, nice staff, clean rooms. Fills the need for a short stay!"

Reviewed on Sep 1, 2026

Pier Blue Inn Old Saybrook - Essex
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
CA $166
CA $224 total
Oct 1 - Oct 2
includes taxes & fees
The Atlantic Hotel
See all 4,698 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.
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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.
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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.
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Shelter Island Historical Society

8.0/10 (1 review)
You can spend time studying the exhibits at Shelter Island Historical Society during your trip to Shelter Island. Stroll along the beaches or experience the area's museums.
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Mashomack Preserve

Explore the great outdoors at Mashomack Preserve, a lovely green space in Shelter Island. Stroll along the beaches or discover the sunsets in this family-friendly area.
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Gardiner's Bay Country Club

Enjoy a round of golf in Shelter Island at Gardiner's Bay Country Club. Stroll along the area's waterfront or simply enjoy its wineries.
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Shelter Island Whale's Tail

10.0/10 (1 review)
You can take time to visit Shelter Island Whale's Tail during your travels to Shelter Island. Wander the beaches and waterfront in the area.
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Menhadden Lane Beach

8.8/10 (3 reviews)
Why not spend a carefree afternoon at Menhadden Lane Beach during your travels in Shelter Island Heights?
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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.
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What to do in Shelter Island

Public Schooner Sail in Greenport

Sunday Brunch Sail in Greenport

CA $242
per adult
Sunday Brunch Sail in Greenport
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 $1,256 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.