Shelter Island Vacations from $245

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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.

The Latest Shelter Island vacation packages

Price found within the past 48 hours. Click for updated prices.
Somerset Hills Hotel, Tapestry Collection by Hilton

Somerset Hills Hotel, Tapestry Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $429, price is now $245 per person
$245
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
8.8/10 Excellent! (221 reviews)
It's a terrific hotel

Reviewed on Oct 20, 2025

Hyatt Regency Jersey City on the Hudson

Hyatt Regency Jersey City on the Hudson

4 out of 5
Downtown Jersey City
Price was $1,432, price is now $767 per person
$767
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,546 reviews)
Great views, helpful staff, very convenient location fot visiting Manhattan.

Reviewed on Oct 23, 2025

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Price was $3,141, price is now $1,711 per person
$1,711
per person
Dec 30 - Jan 4
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.6/10 Exceptional! (151 reviews)
A perfect place to stay!!

Reviewed on Sep 20, 2025

OYO Times Square

OYO Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $478, price is now $272 per person
$272
per person
Jan 2 - Jan 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.2/10 Good! (1,587 reviews)
Basic room, great location

Reviewed on Oct 22, 2025

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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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Coecles Harbor

When in Coecles Harbor, you can plan a visit to Gardiner's Bay Country Club and Mashomack Preserve, some noteworthy sights in the nearby area.

Find hotels in Coecles Harbor

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

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

Wades Beach

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.

Wades Beach

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

$148
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

$179
per adult
76% of travellers recommend
The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC
See all activities in Shelter Island

Shelter Island Hotel Deals

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway, Montauk, NY
$354 nightly
The price is $405 total per night from Nov 20 to Nov 21
$405 total
Nov 20 - Nov 21
Total with taxes and fees
8.2/10 Very Good! (671 reviews)
We had a lovely one night stay. Everyone was very friendly. Having my dogs there was a treat. The spa was great and relaxing. GIGI’s restaurant is a must. The only complaint I have is that the bedclothes need to be updated. They were torn/frayed in multiple places. Other than that it was a great ...

Reviewed on Oct 11, 2025

Gurney's Montauk Resort & Seawater Spa
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
$83 nightly
The price is $96 total per night from Oct 29 to Oct 30
$96 total
Oct 29 - Oct 30
Total with taxes and fees
7.8/10 Good! (1,000 reviews)
Very nice staff, amenities great, an older place, but well kept. Wish there was more than 1 window, a bit stuffy. Felt safe in parking lot and in my room.

Reviewed on Oct 21, 2025

Pier Blue Inn Old Saybrook - Essex
Montauk Blue Hotel

Montauk Blue Hotel

2 out of 5
108 South Emerson Avenue, Montauk, NY
$119 nightly
The price is $136 total per night from Nov 9 to Nov 10
$136 total
Nov 9 - Nov 10
Total with taxes and fees
9.2/10 Wonderful! (162 reviews)
Didn’t get to stay the night had a family emergency had to leave an hour after I checked in. Hope to get credited for another stay in the future. Staff was very nice.

Reviewed on Oct 13, 2025

Montauk Blue Hotel
See all 4,707 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

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Frequently asked questions

How much does a Shelter Island vacation package cost?
Offering excellent value package deals from $245 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.

Explore a world of travel with Expedia

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