Shelter Island Vacations from $905

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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.
Vintedge Residences

Vintedge Residences

Save 100% on your flight
$905
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
No reviews
Seven Beach Lane

Seven Beach Lane

$1,152
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
9.6/10 Exceptional! (24 reviews)
Staff was amazing…..!!!

Reviewed on Aug 7, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

Manhattan
$1,705
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (3,841 reviews)
staff was rude and unhelpful

Reviewed on Aug 7, 2026

The Wall Street Hotel

The Wall Street Hotel

Manhattan
Save 100% on your flight
$986
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.6/10 Exceptional! (726 reviews)
Great service. What you’d expect from a five star hotel in NYC

Reviewed on Aug 7, 2026

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

Manhattan
Save 100% on your flight
$3,472
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (689 reviews)
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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
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 Wades Beach and Shelter Island Historical Society.

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 Sunset Beach and Wades 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 Whale's Tail and Gardiner's Bay Country Club, 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 Gardiner's Bay Country Club and Greenport Carousel are two attractions nearby that you can check out.

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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 Wades Beach and Mashomack Preserve.

Find hotels in Shorewood

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)
Wades Beach offers calm, shallow waters and a broad sandy shoreline perfect for families seeking safe swimming. Lifeguards patrol in summer, and the pavilion provides a comfortable spot to enjoy the tranquil setting.
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A close-up of a beach with various shells and pebbles.

Shell Beach

10.0/10 (1 review)
This peaceful shoreline offers a tranquil escape with abundant shells and wildflowers framing its natural beauty. Enjoy both calm harbor waters and more dynamic waves, perfect for beachcombing and wildlife spotting.
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Gardiner's Bay Country Club

This historic 1896 golf club showcases rolling fairways with stunning views of Gardiner's Bay and Coecles Harbor. Members enjoy challenging play on the Seth Raynor-influenced course and refined dining in the clubhouse.
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Mashomack Preserve

Explore 2,039 acres of pristine wilderness across diverse ecosystems at Mashomack Preserve. The 20+ miles of trails offer intimate encounters with over 200 bird species in tidal creeks, oak forests, and marshes.
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Shelter Island Historical Society

8.0/10 (1 review)
This historic museum preserves Shelter Island's maritime heritage through artifacts and photographs. Explore special exhibits or attend seasonal events celebrating local culture.
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Menhadden Lane Beach

8.8/10 (3 reviews)
This tranquil beach on Shelter Island's east side offers serene views of Gardiner's Bay and the 'Bug' Lighthouse. Bring a blanket, find a quiet spot, and watch sailboats glide across the pristine waters.
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Havens House

Built in 1743, Havens House served as a store, tavern, school, and post office before becoming the Shelter Island Historical Society. Explore its wide plank floors and exhibits showcasing the island's unique heritage.
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What to do in Shelter Island

Public Schooner Sail in Greenport

Sunday Brunch Sail in Greenport

$149
per adult
Sunday Brunch Sail in Greenport
See all activities in Shelter Island

Shelter Island Hotel Deals

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
Fully refundable
$107 nightly
$123 total
Aug 10 - Aug 11
Total with taxes and fees
Pier Blue Inn Old Saybrook - Essex
Sound View Greenport

Sound View Greenport

58775 County Rd 48 Greenport NY
$348 nightly
$397 total
Sep 7 - Sep 8
Total with taxes and fees
Sound View Greenport
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
$219 nightly
$250 total
Sep 8 - Sep 9
Total with taxes and fees
The Atlantic Hotel
See all 4,728 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

Things to do near Shelter Island

Shelter Island offers a perfect getaway for outdoor enthusiasts and couples alike, featuring activities like golfing, skiing, and music concerts. Enjoy a relaxing beach experience with beach chairs for your comfort. Whether you're planning a day trip or a longer vacation, Shelter Island provides a charming atmosphere for those seeking a romantic beach retreat.

Shopping

If you're up for a drive, you can find great shopping options at the Greenport Farmers' Market, located 3 miles away, for fresh local produce and unique gifts. The Style Bar and BookHampton, both 5 miles away, offer stylish apparel and a cozy selection of books, respectively.

Recreation

At Bay Street Theatre, enjoy a captivating performance that blends culture and entertainment, creating a romantic atmosphere for couples or families. Noyac Golf Club offers a refreshing outdoor experience with its scenic golf course, while Cedar Point County Park provides serene trails perfect for wellness and relaxation in nature.

Adventure

At Splish Splash Water Park, located 23 miles from Shelter Island, enjoy thrilling water slides and family-friendly attractions for an exciting day out. For arcade fun, Stay and Play LLC, 16 miles away, offers games and activities perfect for adventurous families. Explore the scenic Walking Dunes Trailhead, also 16 miles away, for a refreshing hike.

Nightlife

Shelter Island offers a laid-back nightlife with cozy bars and intimate lounges. Enjoy live music at local venues, sip craft cocktails at waterfront spots, or unwind at a beach bonfire. The atmosphere is relaxed, perfect for mingling with locals and fellow travelers under the stars.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Shelter Island

Located in New York, Shelter Island is a charming destination perfect for outdoor and romantic beach vacations. Visitors can explore beautiful spots like Crescent Beach and Hay Beach, alongside historic buildings and urban parks. The area offers a rich blend of culture and outdoor experiences, making it ideal for travelers seeking relaxation and adventure in a picturesque setting.

  • 67 Steps Beach: Experience the serene beauty of 67 Steps Beach, just 4 miles from Shelter Island. With its inviting beach vibes, it's a perfect spot for sunbathing, swimming, or a peaceful stroll along the shore, offering a relaxing escape into nature.
  • Gardiner's Bay Country Club: Nestled within Shelter Island, Gardiner's Bay Country Club is a golfer's paradise. Enjoy a round of golf on its stunning course, surrounded by picturesque views and lush landscapes, making it an ideal spot for both seasoned players and beginners alike.
  • Orient Point County Park: Located 8 miles from Shelter Island, Orient Point County Park is a family-friendly urban park. With ample outdoor activities, picnic areas, and scenic views, it’s a great destination for families looking to enjoy nature and city vibes simultaneously.

Best time to go to Shelter Island

The best time to visit Shelter Island is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.6°F (2.0°C)Light RainMostly SunnyAverageModerately Low
February35.8°F (2.1°C)Light RainMostly CloudyAverageModerately Low
March39.7°F (4.3°C)Light RainMostly SunnyAverageModerately Low
April47.5°F (8.6°C)Light RainMostly SunnyAverageAverage
May55.8°F (13.2°C)Light RainMostly SunnyAverageAverage
June64.9°F (18.3°C)Light RainMostly SunnyHighModerately High
July73.0°F (22.8°C)Light RainMostly SunnyHighModerately High
August73.4°F (23.0°C)Light RainMostly SunnyHighModerately High
September68.2°F (20.1°C)Light RainMostly SunnyAverageAverage
October59.7°F (15.4°C)Light RainMostly SunnyLowAverage
November49.6°F (9.8°C)Light RainMostly SunnyLowAverage
December42.1°F (5.6°C)Light RainMostly CloudyLowAverage

Tips to save on your trip to Shelter Island

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Shelter Island.
  • Consider traveling to Shelter Island during the low season (January to March) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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 $905 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.

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