How much does a Shelter Island vacation package cost?

Offering excellent value package deals from ￥309,267 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?

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. 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. 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. 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.

Shelter Island Vacation Packages 2026 from ￥309,267

Name: Montauk Manor
Rating: 9.2

The Latest Shelter Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.

Radio Hotel

Manhattan

￥309,267

per person

Sep 17 - Sep 23

found 1 day ago

Roundtrip non-stop flight included

Osaka (OSA) to New York (JFK)

8.6/10 Excellent! (2,498 reviews)

Cute hotel

Reviewed on Jul 16, 2026

Lotte New York Palace

Manhattan

￥402,198

per person

Sep 28 - Oct 3

found 18 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to New York (JFK)

9/10 Wonderful! (2,127 reviews)

Excellent location

Reviewed on Jul 15, 2026

Hotel Beacon

Manhattan

￥461,873

per person

Sep 17 - Sep 23

found 1 day ago

Roundtrip non-stop flight included

Osaka (OSA) to New York (JFK)

9.4/10 Exceptional! (1,490 reviews)

Comfortable and clean, upgraded to suite which was appreciated! Great neighborhood, easy access into Central Park and Fairway market across the street. Was there with family decades ago, just as nice this time with sister!

Reviewed on Jul 16, 2026

The Hoxton, Williamsburg

￥399,234

per person

Sep 17 - Sep 23

found 1 day ago

Roundtrip non-stop flight included

Osaka (OSA) to New York (JFK)

9/10 Wonderful! (1,006 reviews)

The hotel was great. The food was amazing. We ate at laser Wolf. It was a really fun experience. The restaurants were great. The staff was great. The room was very well appointed but very small very very small and there was no gym in the building and they say they have an arrangement with a gym nearby which they do and it’s wonderful, but it does cost $25 a visit so if you’re going to work out every day it’s going to be expensive. Otherwise, we had a wonderful stay.

Reviewed on Jul 14, 2026

Park Central Hotel New York

Manhattan

￥459,054

per person

Sep 17 - Sep 23

found 1 day ago

Roundtrip non-stop flight included

Osaka (OSA) to New York (JFK)

7.8/10 Good! (4,230 reviews)

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

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	35.6°F (2.0°C)	Light Rain	Mostly Sunny	Average	Moderately Low
February	35.8°F (2.1°C)	Light Rain	Mostly Cloudy	Average	Moderately Low
March	39.7°F (4.3°C)	Light Rain	Mostly Sunny	Average	Moderately Low
April	47.5°F (8.6°C)	Light Rain	Mostly Sunny	Average	Average
May	55.8°F (13.2°C)	Light Rain	Mostly Sunny	Average	Average
June	64.9°F (18.3°C)	Light Rain	Mostly Sunny	High	Moderately High
July	73.0°F (22.8°C)	Light Rain	Mostly Sunny	High	Moderately High
August	73.4°F (23.0°C)	Light Rain	Mostly Sunny	High	Moderately High
September	68.2°F (20.1°C)	Light Rain	Mostly Sunny	Average	Average
October	59.7°F (15.4°C)	Light Rain	Mostly Sunny	Low	Average
November	49.6°F (9.8°C)	Light Rain	Mostly Sunny	Low	Average
December	42.1°F (5.6°C)	Light Rain	Mostly Cloudy	Low	Average

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

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

Fully refundable

￥14,868

￥17,098 total

Jul 23 - Jul 24

includes taxes & fees

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

￥160,594

￥220,174 total

Jul 29 - Jul 30

includes taxes & fees

8.4/10 Very Good! (827 reviews)

"The rooms need to be updated to meet the hotel standards."

Reviewed on Jul 16, 2026

Montauk Manor

236 Edgemere St. Montauk NY

9.2/10 Wonderful! (1,365 reviews)

"Rooms and facilty were clean and room was reasonably spacious. Comfortable bed. Nice kitchenette and balcony. Breakfast in b the restaurant was good. Outdoor pool very nice and heated. Close to most areas of interest. Shuttle available but we did not use."

Reviewed on Jul 9, 2026

Get rates

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.

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Shelter Island Vacations from ￥309,267

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The Latest Shelter Island Vacation Packages

Radio Hotel

Lotte New York Palace

Hotel Beacon

The Hoxton, Williamsburg

Park Central Hotel New York

Where to stay in Shelter Island

Silver Beach

Find the Best Shelter Island Vacation Packages

Things to do in and around Shelter Island

Find the best attractions near Shelter Island

Best time to go to Shelter Island

Tips to save on your trip to Shelter Island

Shelter Island Beach Vacation

Shelter Island Hotel Deals

Pier Blue Inn Old Saybrook - Essex

Gurney's Montauk Resort & Seawater Spa

Montauk Manor

Stay near popular Shelter Island attractions

Wades Beach

What to do in Shelter Island

Private Vacation Photoshoot with Photographer in The Hamptons

The Hamptons Coastal Escape from NYC

Frequently asked questions

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