Shelter Island Vacations from $691

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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.
Lotte New York Palace

Lotte New York Palace

Manhattan
Save 100% on your flight
$691
per person
Jan 2 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (2,282 reviews)
Na

Reviewed on Oct 7, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

Manhattan
Save 100% on your flight
$1,490
per person
Dec 20 - Dec 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (3,389 reviews)
The William Hotel Midtown, New York

The William Hotel Midtown, New York

Manhattan
Save 100% on your flight
$1,368
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.4/10 Exceptional! (258 reviews)
Holiday Inn Express New York City- Wall Street by IHG

Holiday Inn Express New York City- Wall Street by IHG

Manhattan
Save 100% on your flight
$934
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8/10 Very Good! (1,014 reviews)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

Save 100% on your flight
$2,300
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,007 reviews)
They charged us for an umbrella we returned. They also have a deceptive amenity charge- bait and switch. It is false advertising and in appropriate.

Reviewed on Oct 7, 2026

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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 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 Shell 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 Gardiner's Bay Country Club and Mashomack Preserve, some noteworthy sights in the nearby area.

Find hotels in Coecles Harbor
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 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.

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 Wades Beach and Shell Beach.

Find hotels in Shorewood

Stay near popular Shelter Island attractions

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.
See properties
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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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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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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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.
See properties

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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Shelter Island Hotel Deals

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY
$438 nightly
$500 total
Nov 3 - Nov 4
Total with taxes and fees
8.2/10 Very Good! (866 reviews)
"Great"

Reviewed on Oct 6, 2026

Gurney's Montauk Resort & Seawater Spa
Water's Edge Resort & Spa

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
$193 nightly
$222 total
Nov 1 - Nov 2
Total with taxes and fees
8.8/10 Excellent! (1,004 reviews)
"Spa was excellent"

Reviewed on Oct 7, 2026

Water's Edge Resort & Spa
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
Fully refundable
$84 nightly
$97 total
Nov 5 - Nov 6
Total with taxes and fees
Pier Blue Inn Old Saybrook - Essex
See all 4,592 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

Is Shelter Island better suited for a beach vacation or a cultural trip?
Shelter Island is primarily an outdoor and nature destination, making it well-suited for a beach vacation. The island is known for its scenic views and offers numerous beaches, such as Sunset Beach, located about 3 miles from the center, and Wades Beach, about 1 mile away, providing ample opportunities for enjoying the water and coastal scenery.While beaches are a highlight, a Shelter Island vacation can also include recreational and natural attractions. You can visit Gardiner's Bay Country Club for golf, about 1 mile from the center, or explore the Mashomack Preserve, a significant nature area about 3 miles away. For a taste of local flavor, Peconic Bay Winery is about 16 miles from central Shelter Island.
How can I save money on a Shelter Island vacation package?
When you bundle, you can save up to 30%*. To save money on a Shelter Island package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What are the top things to do in Shelter Island?
A Shelter Island vacation offers a blend of natural beauty and outdoor activities:Browse and book things to do in Shelter Island on Expedia.
Do you need to rent a car in Shelter Island, or is public transport enough?
A rental car is highly recommended for a Shelter Island vacation package, as the island is primarily an outdoor and nature destination with attractions spread out. While walking and riding a bike are options for shorter distances, a car provides the most flexibility to explore the island's various beaches and natural sights.Having a car allows you to easily reach popular spots like Sunset Beach or the expansive Mashomack Preserve. For Shelter Island vacation packages with flights, a rental car allows you to fully experience all the island has to offer, from its scenic views to its many outdoor activities.
Can I change or cancel my Shelter Island vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Shelter Island vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Shelter Island vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Shelter Island vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Shelter Island?
To find last-minute vacation packages to Shelter Island, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Shelter Island vacation packages?
Free cancellation on a Shelter Island vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Shelter Island vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Shelter Island getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Shelter Island vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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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.