Shelter Island Vacations from ￥275,736

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The Latest Shelter Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Pestana CR7 Times Square

Pestana CR7 Times Square

Manhattan
￥275,736
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to New York (JFK)
9.2/10 Wonderful! (1,026 reviews)
The room itself was nice. The hotel is extremely understaffed and lacks urgency with their guests.

Reviewed on Aug 30, 2026

The High Line Hotel

The High Line Hotel

Manhattan
Save 100% on your flight
￥353,159
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to New York (JFK)
8.6/10 Excellent! (1,003 reviews)
Great hotel with lots of charm.

Reviewed on Aug 30, 2026

NobleDEN Hotel

NobleDEN Hotel

Manhattan
￥401,994
per person
Oct 31 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9.8/10 Exceptional! (1,662 reviews)
Loved this hotel! Would definitely come back. Staff was very welcoming and room was super cute. Good location close to little Italy and Chinatown. Loved the access to the rooftop.

Reviewed on Aug 29, 2026

WestHouse Hotel New York, an SLH Hotel

WestHouse Hotel New York, an SLH Hotel

Manhattan
Save 100% on your flight
￥418,518
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to New York (JFK)
8.4/10 Very Good! (1,003 reviews)
It said it was a 5 star hotel but I don't think it was 5 star. Nice location

Reviewed on Aug 31, 2026

Ink 48 Hotel

Ink 48 Hotel

Manhattan
￥350,010
per person
Oct 12 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
8.4/10 Very Good! (1,772 reviews)
Excellent property, still my first choice

Reviewed on Aug 30, 2026

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 Shelter Island Historical Society and Sunset Beach.

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 Crescent Beach and Sunset 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 Historical Society and Mashomack Preserve, 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 Greenport Carousel and Greenport Harbor Brewing Company 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 Mashomack Preserve and Shelter Island Historical Society.

Find hotels in Shorewood

Find the Best Shelter Island Vacation Packages

Things to do in and around Shelter Island

Shopping

For a delightful shopping experience in Shelter Island, visit the Greenport Farmers' Market, only 4.8km away, for local goods. The Style Bar, located 8.0km away, offers trendy clothing. If you're up for a drive, check out Love Lane, 17.7km away, featuring charming shops and a family-friendly atmosphere.

Recreation

Enjoy the serene atmosphere at Cedar Point County Park, perfect for relaxation and nature walks. For some fun, head to Shelter Island Whale's Tail for a mini-golf adventure with family. Don’t miss Bay Street Theatre for a captivating performance, blending culture and entertainment in a romantic setting.

Adventure

Experience the Greenport Carousel, a charming ride offering outdoor family fun located 4.8km away. For a thrilling day, head to Splish Splash Water Park, 24.8km from Shelter Island, where adventure and entertainment await. Enjoy arcade games and excitement at Stay and Play LLC, located 25.7km away.

Nightlife

Shelter Island offers a charming nightlife scene. Start your evening at the lively Sunset Beach for cocktails with a view. For a more laid-back vibe, visit The Chequit, where you can enjoy local brews and live music, creating a perfect blend of relaxation and entertainment.

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

Find the best attractions near Shelter Island

Explore the charm of Shelter Island, perfect for outdoor adventures and romantic beach getaways. Discover beautiful spots like Crescent Beach and Hay Beach, along with local parks and historic buildings that offer a cultural experience for families and travelers alike. Whether you're seeking relaxation by the shore or exploring the island's rich history, Shelter Island has something for everyone to enjoy.

  • Crescent Beach: Experience the serene beauty of Crescent Beach, located 3.2km from Shelter Island. With its soft sands and gentle waves, it's the perfect spot for beach vibes, sunbathing, swimming, or simply enjoying a peaceful stroll along the shore.
  • Railroad Museum of Long Island: Just 4.8km away, immerse yourself in the rich history of railroads at this cultural gem. Explore fascinating exhibits, vintage train cars, and learn about the evolution of rail travel in the region, making it a must-visit for history enthusiasts.
  • LongHouse Reserve: Located 14.5km from Shelter Island, this stunning sculpture garden offers a unique blend of art and nature. Wander through beautifully landscaped grounds filled with contemporary sculptures, perfect for families and outdoor lovers seeking inspiration and tranquility.

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 (2 kilometers 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 Hotel Deals

Sound View Greenport

Sound View Greenport

58775 County Rd 48 Greenport NY
￥41,782
￥61,454 total
Sep 15 - Sep 16
includes taxes & fees
Sound View Greenport
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
Fully refundable
￥14,960
￥17,204 total
Sep 28 - Sep 29
includes taxes & fees
8/10 Very Good! (1,002 reviews)
"My room smelled like urine and the lobby smelled like a wet dog. Bathroom was dim and dingy, ironing board stained, A/C vents were full of dust and didn’t work well. TV didn’t work either. How they can charge $150 for a room here is appalling. The front sign is the only thing nice about the property- ..."

Reviewed on Aug 28, 2026

Pier Blue Inn Old Saybrook - Essex
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
￥22,909
￥30,175 total
Oct 1 - Oct 2
includes taxes & fees
The Atlantic Hotel
See all 4,699 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.

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.
See properties
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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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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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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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.
See properties

What to do in Shelter Island

Public Schooner Sail in Greenport

Sunday Brunch Sail in Greenport

￥23,742
per adult
Sunday Brunch Sail in Greenport
Private Vacation Photoshoot with Photographer in The Hamptons

Private Vacation Photoshoot with Photographer in The Hamptons

￥45,088
per adult
Private Vacation Photoshoot with Photographer in The Hamptons
The Hamptons Coastal Escape from NYC

The Hamptons Coastal Escape from NYC

￥148,513
per traveler
The Hamptons Coastal Escape from NYC
See all activities in Shelter Island

Frequently asked questions

How much does a Shelter Island vacation package cost?
Offering excellent value package deals from ￥275,736 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.

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.