Shelter Island Holidays
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Top Flight + Hotel Deals in Shelter Island
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Manhattan Times Square
Manhattan
€1,892
per person
3 Dec - 8 Dec
found 21 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (3,950 reviews)
Had a great experience at Rui. The room was clean, staff were so friendly and helpful. Check in and out was fast and efficient. Had a wonderful experience.
Reviewed on 20 Sept 2026
Ink 48 Hotel
Manhattan
€1,009
per person
5 Nov - 11 Nov
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
8.4/10 Very good! (1,767 reviews)
The Ink48 now for several years is one of my/our go to places in NYC; the rooms are still attractively shaped, the renovated breakfast restaurant is stylish and the food from the menu tasty and reasonably priced with the evening roof top place still hip and menu interesting (the view in all directions is still beautiful). However the front desk has lost some of its a-tentativeness, we now have a routine to immediately ask for extra towels and washcloths at time of check-in. While the room bar is stacked, the selection of amnemities is poor (can’t get a hot cup of water for bedtime tea, no coffee machine, q-tips, extra toothbrush?). A real bummer this time was the waiting time to receive the car back from valet, 1h20 minutes… and we were not alone. A couple needed to return their rental to catch an EWR flight; hope they made it! We were to pickup someone arriving by train and arrived severely delayed! The present INK48 valet arrangement is not acceptable; be forewarned!
Reviewed on 20 Sept 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
Silver Beach
While Silver Beach may 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 Crescent Beach.
Menantic Creek
While there might not be top attractions in Menantic Creek, you can explore the larger area and discover places like Shelter Island Historical Society and Sunset Beach.
Coecles Harbor
While Coecles Harbor isn't home to many top sights, Shelter Island Historical Society and Mashomack Preserve are some notable places to visit nearby.
Hay Beach
When in Hay Beach, you can plan a visit to Greenport Carousel and Greenport Harbor Brewing Company, some noteworthy sights in the nearby area.
Shorewood
While Shorewood may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Mashomack Preserve and Shelter Island Historical Society.
Shelter Island Beach Holiday
There's nothing like a Shelter Island holiday 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 centre on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometres 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.
Top hotels in Shelter Island
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
€81
8 Oct - 9 Oct
includes taxes & fees
Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
€470
29 Sept - 30 Sept
includes taxes & fees
Sound View Greenport
58775 County Rd 48 Greenport NY
€289
14 Oct - 15 Oct
includes taxes & fees
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
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.
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 harbour waters and more dynamic waves, perfect for beachcombing and wildlife spotting.
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.
Shelter Island Historical Society
8.0/10 (1 review)
This historic museum preserves Shelter Island's maritime heritage through artefacts and photographs. Explore special exhibits or attend seasonal events celebrating local culture.
Gardiner's Bay Country Club
This historic 1896 golf club showcases rolling fairways with stunning views of Gardiner's Bay and Coecles Harbour. Members enjoy challenging play on the Seth Raynor-influenced course and refined dining in the clubhouse.
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.
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.
What to do in Shelter Island
Private Vacation Photoshoot with Photographer The Hamptons
€245
per adult
Frequently asked questions
How much does a Shelter Island holiday package cost?
Offering excellent value package deals from €971 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
