Shelter Island Vacations

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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 Sunset Beach and Crescent Beach.

Find hotels in Silver Beach

Find the Best Shelter Island Vacation Packages

Shelter Island Beach Vacation

There's nothing that can beat a Shelter Island vacation. Whether you're enjoying refreshing margaritas at a local hot spot or reading your favorite book by the ocean's edge, your trip to Shelter Island is the time to live out your beachy dreams. Many will suggest you stay close to Wades Beach, situated just 2 kilometers from downtown. However, you'll also discover a fantastic range of Shelter Island vacation deals around Menhadden Lane Beach and Shell Beach, two other well-liked nearby options.

Shelter Island Hotel Deals

Montauk Yacht Club
Montauk Yacht Club
4 out of 5
32 Star Island Rd, Montauk, NY
The price is NT$7,773 per night from Apr 27 to Apr 28
NT$7,773
NT$8,880 total
includes taxes & fees
Apr 27 - Apr 28
8.4/10 Very Good! (1,003 reviews)
"Beautiful place. Wonderful staff"

Reviewed on 2025/4/25

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 NT$2,569 per night from Apr 27 to Apr 28
NT$2,569
NT$2,955 total
includes taxes & fees
Apr 27 - Apr 28
7.6/10 Good! (932 reviews)
"Great night’s sleep."

Reviewed on 2025/4/18

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 NT$5,496 per night from May 6 to May 7
NT$5,496
NT$6,881 total
includes taxes & fees
May 6 - May 7
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 2025/4/22

Water's Edge Resort & Spa
See all 4,697 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.

Frequently asked questions

How much does a Shelter Island vacation package cost?
Offering excellent value package deals on Expedia, you’ll be surprised at how little a vacation to Shelter Island costs! Expedia’s packages make travel planning easier and your savings go further.
What are the cheapest months to go to Shelter Island?
To pick up cheap Shelter Island vacation packages, plan your trip outside of peak periods like public holidays and major festivals. You’ll typically find better availability and lower prices for flights and hotels.
How many days is enough for Shelter Island?
We recommend booking a Shelter Island vacation for at least 5 days. This will give you time to visit major attractions such as Menhadden Lane Beach and Havens House, and also check out neighborhoods like Greenport West and The Heights. You might even be able to squeeze in a day trip outside of Shelter Island.
Is it worth booking a vacation package to Shelter Island?
It’s easy to see why a Shelter Island vacation is on the to-do list of many travelers. Leading attractions like Shell Beach are just the start of things to keep you busy here.
How to find the best Shelter Island package deals?
Bagging a cheap Shelter Island package deal is a breeze with Expedia. Once you’ve entered your trip dates and destination under our “Packages” tab, set your maximum budget, apply a few filters and browse what’s available. You can tweak your search by “Property class,” “Number of bedrooms,” “Traveler experience” and more. Sort the results by “Price: low to high” to view the most affordable Shelter Island package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Shelter Island vacation as a package?
You can enjoy significant savings on your next Shelter Island getaway by booking a customized vacation package. Click on the “Package” heading, then enter your travel dates and destination to view the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Shelter Island?
Land amazing discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Shelter Island getaway.
How to plan a trip to Shelter Island?

  1. Pick your travel dates: What you’d like to do in Shelter Island and your favorite season will help you decide when to get away.
  2. Figure out your budget: Ensure you have enough money to cover everything from dining out and transportation to activities and airfares. Your accommodations will likely be the largest expense during your trip to Shelter Island.
  3. Decide how many days away: Start by making a list of all the activities and sights you’d like to experience in Shelter Island. Then, estimate how long you’ll need at each, as well as any travel time.
  4. Bundle your airfare and accommodations: After you’ve settled on your travel dates and duration, lock in the perfect Shelter Island vacation package for you.

Discover the most popular places to visit in Shelter Island

Shelter Island Historical Society

4/5(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.

Shelter Island Historical Society

Shell Beach

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.

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