Shelter Island Vacations from $295

Book a Hotel + Flight or Car together to unlock savings

Photo by Brian V. Rowe

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    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.

The Latest Shelter Island vacation packages

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 18 - Sep 21
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
7/10 Good! (2,051 reviews)
Lots of space and great location k

Reviewed on Jul 3, 2025

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
per person
Aug 16 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,001 reviews)
We love Loews Regency NYC. The staff is exceptional and the rooms are very comfortable.

Reviewed on Jun 29, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,004 reviews)
One of the Best hotel I have ever stayed. Little small, little pricey, but they did everything right.

Reviewed on Jun 25, 2025

Night Hotel Broadway

Night Hotel Broadway

2.5 out of 5
Manhattan
Save 100% on your flight
per person
Sep 4 - Sep 9
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7/10 Good! (2,136 reviews)
The staff was really friendly. Always helpful! Security was great. I think a really good update in flooring/carpet would be a great touch.

Reviewed on Jul 5, 2025

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
per person
Sep 13 - Sep 18
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
9.2/10 Wonderful! (617 reviews)
We loved our stay at the Lotte Towers! The rooms were very spacious for our family of 4. We were provided a fridge on request. The views were amazing. The lifts were quick to get us to the 58th floor! Our rooms were serviced twice daily. Cannot fault anything at Lotte would love to return one day!!

Reviewed on Apr 15, 2025

Don't see what you're looking for?
See all available trips from Columbus to Shelter Island
View all trips

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
Default Image

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 Shell Beach.

Find hotels in Menantic Creek

Discover the most popular places to visit in Shelter Island

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.

Gardiner's Bay Country Club

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

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.

Mashomack Preserve

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

$159
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
See all activities in Shelter Island

Shelter Island Hotel Deals

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
$111 nightly
The price is $127 total per night from Jul 13 to Jul 14
$127 total
Jul 13 - Jul 14
Total includes taxes and fees
7.6/10 Good! (1,002 reviews)
"Great location and pool, close to a wonderful restaurant"

Reviewed on Jun 30, 2025

Quality Inn Old Saybrook - Westbrook
Montauk Yacht Club
Montauk Yacht Club
4 out of 5
32 Star Island Rd, Montauk, NY
$609 nightly
The price is $696 total per night from Jul 6 to Jul 7
$696 total
Jul 6 - Jul 7
Total includes taxes and fees
8.4/10 Very Good! (1,000 reviews)
"My only complaint is that the pool for children is very far from the main pool and beach. The property did not advertise the separate pools and it was a bummer as I had my 16 year old daughter with me who did not want to go to a pool with small children yet she was refused at the adult pool."

Reviewed on Jul 2, 2025

Montauk Yacht Club
Gurney's Montauk Resort & Seawater Spa
Gurney's Montauk Resort & Seawater Spa
4 out of 5
290 Old Montauk Highway, Montauk, NY
$864 nightly
The price is $987 total per night from Jul 9 to Jul 10
$987 total
Jul 9 - Jul 10
Total includes taxes and fees
8.2/10 Very Good! (642 reviews)
"We were able to check in early. Nice staff"

Reviewed on Jun 23, 2025

Gurney's Montauk Resort & Seawater Spa
See all 4,803 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.

Find the Best Shelter Island Vacation Packages

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 center on your trip to Shelter Island, find a hotel around Wades Beach (1 mile 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.

Shelter Island Essential Information

Language
English
Currency
U.S dollars
Population
1,350
Max Temp Winter
40ºF
Max Temp Summer
75ºF
Top Sights
Wolffer Estates Vineyard, East Hampton Main Beach and 67 Steps Beach

More vacations you might like

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Shelter Island vacation package cost?
Offering excellent value package deals from $295 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?
If you're looking to score a cheap Shelter Island vacation package, consider visiting in January, October and December. You'll usually find better rates on flights and accommodations during these quieter months --- perfect for a budget-friendly getaway.
How many days is enough for Shelter Island?
Dedicate at least 4 days for your Shelter Island vacation to enjoy everything that makes this destination special. Explore popular areas, including The Heights and Greenport West. Then make a beeline for top attractions like Menhadden Lane Beach and Mashomack Preserve. With a clever itinerary, you can keep busy with room for some me-time too. Want to travel beyond Shelter Island? Consider squeezing in an excursion or two.
Is it worth booking a vacation package to Shelter Island?
Shelter Island is a good vacation destination with attractions like Shell Beach among the many things to keep you entertained. Whether you're heading away with the family or getting away with friends, a Shelter Island vacation promises fun for everyone.
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 the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Shelter Island.
  2. Work out your budget: Make sure you have enough money to pay for everything from meals and transportation to experiences and flights. Your accommodations will probably be the largest expense during your trip to Shelter Island.
  3. Organize your Shelter Island getaway with Expedia's trip planning tool: Look for and book hotels and experiences all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Shelter Island together.
  4. Decide your trip length: Think about how much time you want to spend exploring Shelter Island. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
  5. Bundle your airfare and accommodations: After you've settled on your trip dates and duration, lock in the right Shelter Island vacation package for you.
  6. Book any excursions or activities: Now to the fun part --- organizing everything you want to do and see. Explore some of the best things to do in Shelter Island in Shelter Island and book your tickets early to save time (and maybe some cash too!).

Does Expedia offer Book Now, Pay Later Shelter Island vacation packages?
If you're anything like us, you love traveling the world but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the overall cost of your Shelter Island trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.