How much does a Shelter Island vacation package cost?

Offering excellent value package deals from $288 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?

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. 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. 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. 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. 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. 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 Shelter Island Vacation Book from $288

Name: Sound View Greenport
Price range: $196 total
Rating: 8.4

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.

Hotel St. James

Manhattan

$288

per person

Apr 24 - Apr 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

8.8/10 Excellent! (6,546 reviews)

Everything about hotel was amazing

Reviewed on Feb 3, 2026

Topping Rose House

$339

per person

Mar 6 - Mar 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

9.2/10 Wonderful! (136 reviews)

Great rooms, staff and food

Reviewed on Sep 28, 2025

Hotel Riu Plaza Manhattan Times Square

Manhattan

Save 100% on your flight

$399

per person

Apr 24 - Apr 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

9.2/10 Wonderful! (3,348 reviews)

Clean rooms and space in room.

Reviewed on Feb 2, 2026

The Inn At Fox Hollow Hotel

Save 100% on your flight

$629

per person

Apr 18 - Apr 22

found 13 hours ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

9.2/10 Wonderful! (1,002 reviews)

Normally my absolute Favorite Hotel while visiting my family on Long Island, I froze Both nights in my room the temperature never reached above 67°, no matter how high I turned up the heat, luckily I found an extra blanket it the closet, helped a bit but was so very uncomfortably cold… the bellhops were just so wonderful about bringing my luggage to and from my car to room and back to car💜, and room service was prompt and the staff courteous!! I went to desk to buy some water and asked for some more Tea k cups and some cramer, and it was not put in the bag of water bottles and when I realized it, I called down to the desk and they never brought it to me as promised. Upon checkout, I left my 1st Edition book on the bed and having already left, called the front desk to inquire if I could return and pick it up, was told they did not have it and transferred me to Housekeeping- they never answered the phone and I left a message and nobody has yet to return my call… I KNOW I left the book there on the bed and it is very unsettling that the staff didn’t seem to care that I wanted my property returned to me… I was still on Long Island and I would’ve gladly come to pick up my book, now I am home without it… your hotel has always had such wonderful customer service, please don’t let it slip. I will pay for my book to be sent back to me. I really want it returned It’s called Pendergast the beginning. It’s a hardcover first edition book. I can be reached at 631-278-5881. Thank you.

Reviewed on Feb 2, 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

Shelter Island Hotel Deals

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

$371 nightly

$424 total

Feb 5 - Feb 6

Total with taxes and fees

8.2/10 Very Good! (720 reviews)

Staying at Gurney's after their many renovations was surprising !! The rooms don't look outdated anymore including the Spa / Pool area - for the price you're paying per night, I appreciated the face lift. Oceanviews from any angle of this hotel site will always be incredible !

Reviewed on Jan 12, 2026

Montauk Blue Hotel

108 South Emerson Avenue Montauk NY

9.2/10 Wonderful! (188 reviews)

Great view of sunrise and sunset

Reviewed on Jan 19, 2026

Get rates

Sound View Greenport

58775 County Rd 48 Greenport NY

$172 nightly

$196 total

Feb 9 - Feb 10

Total with taxes and fees

8.4/10 Very Good! (609 reviews)

This is our fourth trip back to the Soundview Inn, and we are big fans! The atmosphere is simple, modern, with a laid-back vibe. The rooms are well appointed and are finished with an indoor/outdoor use in mind. The room can be chilly in the winter, but it’s easy to get cozy. The included breakfast ...

Reviewed on Jan 10, 2026

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.

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.

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 (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.

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

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