Shelter Island Heights Holidays

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Top Flight + Hotel Deals in Shelter Island Heights

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

Ink 48 Hotel

Manhattan
Save 100% on your flight
€1,003
per person
13 Nov - 19 Nov
found 1 day ago
Return flight included
Shannon (SNN) 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

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

Manhattan
€1,892
per person
3 Dec - 8 Dec
found 1 day 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

The William Hotel Midtown, New York

The William Hotel Midtown, New York

Manhattan
Save 100% on your flight
€1,216
per person
13 Nov - 19 Nov
found 1 day ago
Return flight included
Shannon (SNN) to New York (JFK)
9.4/10 Exceptional! (232 reviews)
The staff are wonderful, helpful, and so kind!

Reviewed on 20 Sept 2026

Night Hotel Broadway

Night Hotel Broadway

Manhattan
Save 100% on your flight
€1,298
per person
3 Dec - 10 Dec
found 1 day ago
Return flight included
Shannon (SNN) to New York (JFK)
7.6/10 Good! (3,584 reviews)
Very good and comfy

Reviewed on 21 Sept 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

Manhattan
Save 100% on your flight
€1,601
per person
11 Dec - 15 Dec
found 22 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (3,331 reviews)
Very clean modern hotel close to Times Square with great full buffet breakfast included.

Reviewed on 20 Sept 2026

Shelter Island Heights Beach Holiday

Escape the stresses of everyday life and let your body, mind and soul unwind on your Shelter Island Heights holiday. There's nothing more invigorating than the smell of salty sea air and the soothing melody of waves lapping at the shore. Plan your trip to Shelter Island Heights the easy way by choosing one of our Shelter Island Heights holiday packages. Many tourists choose to base themselves near Crescent Beach, a must-see just 2 kilometres from the downtown area.

Things You Should Know About Shelter Island Heights

  • Check into one of our Shelter Island Heights beach hotels to appreciate the best this destination has to offer. Wander along the water's edge and be inspired by the stunning sunrises just moments from your front door.
  • Alternatively, check out our range of private holiday homes. They're popular with travellers planning a stay in Shelter Island Heights. Consider Shelter Island House and The Chequit.
  • There are tons of activities that keep the 1,050 or so residents of Shelter Island Heights occupied. Browsing our Shelter Island Heights things to do page will let you in on the best of what this place has to offer.
  • Land great deals with a Shelter Island Heights holiday package. With the money you save, you won't regret indulging in this destination's best offerings. Sunset Beach, Crescent Beach and Crescent Beach are excellent places to start.

Top hotels in Shelter Island Heights

The Chequit

The Chequit

23 Grand Ave Shelter Island Heights NY
€206
4 Oct - 5 Oct
includes taxes & fees
The Chequit
The Pridwin Hotel

The Pridwin Hotel

81 Shore Road Shelter Island Heights NY
Get rates
The Pridwin Hotel
Pier Blue Inn Old Saybrook - Essex

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
Pier Blue Inn Old Saybrook - Essex
See all 4,682 properties in Shelter Island Heights
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 Heights attractions

Crescent Beach

9.4/10 (13 reviews)
Why not spend a care-free afternoon at Crescent Beach during your travels in Shelter Island Heights? Experience the area's entertainment choices and theatre scene.
See properties

Menhadden Lane Beach

8.8/10 (3 reviews)
Why not spend a care-free afternoon at Menhadden Lane Beach during your travels in Shelter Island Heights?
See properties

Shelter Island Country Club

10.0/10 (3 reviews)
Enjoy a round of golf in Shelter Island Heights at Shelter Island Country Club. Stroll along the beaches or discover the area's sunsets.
See properties

Sylvester Manor

8.8/10 (3 reviews)
You can find out about the history of Shelter Island Heights when you stop by Sylvester Manor. Stroll along the beaches or discover the area's sunsets.
See properties

What to do in Shelter Island Heights

Public Schooner Sail in Greenport

Sunday Brunch Sail in Greenport

€151
per adult
Sunday Brunch Sail in Greenport
Private Vacation Photoshoot with Photographer The Hamptons

Private Vacation Photoshoot with Photographer The Hamptons

€245
per adult
Private Vacation Photoshoot with Photographer The Hamptons
See all activities in Shelter Island Heights

Frequently asked questions

How much does a Shelter Island Heights holiday package cost?
You'll find cheap prices from €1,003 on Expedia for your Shelter Island Heights getaway. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your holiday to Shelter Island Heights costs.
What are the cheapest months to go to Shelter Island Heights?
If you're hoping to score a cheap Shelter Island Heights holiday package, consider visiting in December, January and February. You're likely to find better rates on airfares and hotels during these months — perfect for a budget-friendly break.
How many days is enough for Shelter Island Heights?
Allow at least 2 days for your Shelter Island Heights holiday to discover everything that makes this place special. Wander around key areas, including Greenport West and The Heights. Then check out top sights such as Sylvester Manor and Sunset Beach. With a clever itinerary, you'll be kept busy with room for some rest and relaxation too. Want to travel outside of Shelter Island Heights? Consider fitting in a day trip or two.
Is it worth booking a holiday package to Shelter Island Heights?
Shelter Island Heights is a good holiday destination with attractions like Crescent Beach among the many things to keep you busy. Whether you're travelling with the family or getting away with friends, a Shelter Island Heights holiday promises fun for everyone.
How to find the best Shelter Island Heights package deals?
Use Expedia's handy filters to help you find some of the best Shelter Island Heights package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Shelter Island Heights package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your holiday package as early as possible.
Is it cheaper to book a Shelter Island Heights holiday as a package?
You can enjoy significant savings on your Shelter Island Heights escape by booking a tailored holiday package. Click on the "Package" heading, then enter your destination and travel dates to see the best airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Shelter Island Heights?
Score incredible bargains by booking your flights in advance with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Shelter Island Heights break.
How to plan a trip to Shelter Island Heights?
  1. Choose when to travel: Check your schedule and pack your bags. Your preferred season and the type of activities available will also help you decide when to visit Shelter Island Heights.
  2. Plan your budget wisely: On top of the cost of your stay, you should factor in other expenses too. These include flights, transportation and food. Also, put aside some extra funds for unexpected costs that could crop up during your trip to Shelter Island Heights.
  3. Decide how long to go away for: Now that you're up to speed on Shelter Island Heights, you can figure out the ideal length of your break. Pull together a draft plan and give yourself enough time for all the things you want to do.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to pick a Shelter Island Heights holiday package that brings all your bookings together.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.