Shelter Island Holidays
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Top Shelter Island flight + hotel deals
- Sela V Hotel
26 Dec - 30 DecSela V Hotel + Flight
Brooklyn4 nights4.0 star property9.2/10 - Wonderful (421 reviews)Return • Montreal (YUL) - New York (JFK)YUL - EWR • Direct EWR - YUL • Direct€1,012€701found 6 hours agoper traveller - Ink 48 Hotel
18 Dec - 23 DecInk 48 Hotel + Flight
Manhattan5 nights4.5 star property8.4/10 - Very good (1,837 reviews)"The staff are the Superhero of this hotel. The hotel does need to be a little more clean & maybe a humidifier - the room was dry & carpet seems dirty. However amazing location & the staff is A+"Reviewed November 9, 2026Return • Dublin (DUB) - New York (JFK)DUB - EWR • Direct LGA - DUB • 1 stop€2,158€1,452found 14 hours agoper traveller - 1 Hotel Central Park
18 Dec - 22 Dec1 Hotel Central Park + Flight
Manhattan4 nights5.0 star property9.0/10 - Wonderful (1,008 reviews)"Lovely hotel and great location. Loved it. I rated it good because I arrived early and as expected my room wasn't yet ready. No problem. I left my bags and asked that they be taken up when the room was ready. I came back much later in the day (after check in time) and room wasn't yet ready and my bags of course weren't taken up. When I expressed some frustration, the situation was immediately resolved. But, I still don't get the delay. They tried to make it up to me by leaving a bottle of..."Reviewed November 9, 2026Return • Dublin (DUB) - New York (JFK)DUB - JFK • Direct JFK - DUB • 1 stop€3,868€2,620found 1 day agoper traveller - Margaritaville Resort Times Square
18 Dec - 23 DecMargaritaville Resort Times Square + Flight
Manhattan5 nights4.0 star property9.0/10 - Wonderful (4,179 reviews)Return • Dublin (DUB) - New York (JFK)DUB - EWR • Direct LGA - DUB • 1 stop€2,308€1,567found 14 hours agoper traveller - Aura Hotel Brooklyn
26 Dec - 30 DecAura Hotel Brooklyn + Flight
Brooklyn4 nights4.0 star property8.0/10 - Very good (1,350 reviews)"This is a hardcore orthodox Jewish area, no cafe, no entertainment, no restaurants, no nothing but a very close knitted Orthodox Jews that won’t communicate with others. The nearest subway station is about 1KM. The area is rough and unclean. With this price, should have gone to some neighbourhood better."Reviewed November 9, 2026Return • Montreal (YUL) - New York (JFK)YUL - EWR • Direct EWR - YUL • Direct€1,142€790found 6 hours agoper traveller
Where to stay in Shelter Island
Silver Beach
Silver Beach offers a tranquil coastal retreat on Shelter Island with direct access to the sound. This charming area features weathered cottages and natural shorelines perfect for peaceful waterfront strolls. Shell Beach provides a serene spot for swimming and sunbathing. The neighborhood's calm waters make it ideal for kayaking and small boat activities. Enjoy the scent of salt air mixed with pine and beach roses. Most visitors bring supplies or travel to nearby island markets since Silver Beach maintains its residential character.
Coecles Harbor
Coecles Harbour offers a peaceful retreat where pristine waterfront paths wind along Peconic Bay. Luxury yachts and sailboats dot the protected marina, creating a classic New England coastal scene. Wooden docks extend into calm waters, providing perfect sunset viewing spots. This upscale Shelter Island area balances authentic maritime character with holiday amenities. Visitors can enjoy swimming at Menhadden Lane Beach or explore by kayak and paddleboard. The quiet atmosphere, with only the sounds of lapping waves and seabirds, makes it ideal for those seeking a serene coastal escape.
Menantic Creek
Menantic Creek on Shelter Island offers a peaceful waterfront escape where natural beauty takes centre stage. This residential haven features classic Hamptons-style homes with private docks nestled among mature trees. The winding creek waters create a tranquil backdrop for a truly authentic island experience. The area provides excellent opportunities for kayaking, paddleboarding, and birdwatching along pristine shorelines. Visitors can easily explore nearby attractions like Wades Beach and Shelter Island Historical Society. Those seeking quiet relaxation will appreciate the gentle creek sounds and salt-tinged air that define this serene coastal retreat.
Hay Beach
Hay Beach offers a tranquil peninsula retreat on Shelter Island, away from the bustling Hamptons scene. This residential haven is surrounded by water on three sides with several beach access points for scenic coastal views. Private waterfront homes and cottages create a peaceful atmosphere where natural beauty takes centre stage. Visitors can explore Menhadden Lane Beach or take short trips to nearby Gardiner's Bay Country Club. The neighborhood's charm lies in its uncrowded shoreline paths and pristine waters. Perfect for kayaking, swimming, and sunset watching, Hay Beach delivers a genuine low-key coastal experience.
Shorewood
Shorewood offers a peaceful retreat on Shelter Island with pristine shorelines and scenic waterfront paths. Classic Hamptons-style cottages with cedar shingles and white trim line the quiet, tree-lined streets. The neighborhood's charm lies in its natural beauty and exclusive residential character. Wades Beach beckons with sandy shores and calm bay waters perfect for swimming and kayaking. Visitors appreciate the minimal tourist crowds and opportunities for stargazing at night. The salt air mingles with pine scents while gentle waves create a soothing natural soundtrack.
Discover the most popular places to visit in Shelter Island
What to do in Shelter Island
Private Vacation Photoshoot with Photographer The Hamptons
Shelter Island Hotel Deals
"We went for a nice weekend getaway and we were not disappointed. The room was really nice, the coffee shop was perfect for a morning latte and cup of coffee. We went to the bar and restaurant both days and the staff were absolutely amazing and professional and provided quality service. The food and drinks were amazing. We wanted peace and tranquility and that’s exactly what we got."
Silver Sands Motel & Beach Bungalows
Silver Sands Motel & Beach Bungalows"What a perfect getaway destination on the water! This renovated 1950s motel has a retro, luxurious feel with reasonable off-season pricing. Julia and David were so warm and helpful, offering good communication beforehand on the check-in process and a welcoming glass of Prosecco plus free lattes upon request. The lobby is cheerful and stylish, and the room (standard queen) very comfortable. We splurged on a spa treatment and our wellness center visit was the highlight of our 3 night stay. Highly...
"Such a cute place to stay! Bill was super kind and helpful! I was only in for a quick night but I would definitely stay here again!!"
"The room was great. The staff was excellent and very helpful. We enjoyed the location."
"Location is nice. But many times booked for weddings so you won’t be able to go to the bar etc. The rooms are clean and fine but for the pricing I expected nicer. Feels more like a cabin. They also have fees that are not represented on an app like Expedia if you book through them. An additional 30 for overnight parking when you are paying 600 a night for a mediocre room on Long Island in November you would expect that to be included. Overall would not stay again there are much better options....
Frequently Asked Questions
How much does a Shelter Island holiday package cost?
Offering excellent value package deals from €701 on Expedia, you'll be surprised at how little a holiday 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 holiday 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 holiday 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 neighbourhoods 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 holiday package to Shelter Island?
It's easy to see why a Shelter Island holiday is on the to-do list of many travellers. 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," "Traveller 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 travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Shelter Island holiday as a package?
You can enjoy significant savings on your next Shelter Island getaway by booking a customised holiday 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 holiday 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 favourite 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 accommodation 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 accommodation: After you've settled on your travel dates and duration, lock in the perfect Shelter Island holiday package for you.