Shelter Island Heights Holidays from £933

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Your Shelter Island Heights Holiday

The easiest way to experience this interesting city is with a customised Shelter Island Heights holiday package. Base yourself in the neighbourhood of Orient Point, which is good for views, fishing and nature or go someplace else — our package deals are all about you. Make your trip to Shelter Island Heights even more fulfilling by going sightseeing. 67 Steps Beach, Railroad Museum of Long Island and Kontokosta Winery are some of the top attractions you'll want to explore. Browse Expedia's wide range of travel options and book your ultimate holiday to Shelter Island Heights today.

Top Shelter Island Heights Flight + Hotel Deals

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

San Carlos Hotel

4.5 out of 5
Manhattan
Price was £1,406, price is now £933 per person
£933
per person
17 Aug - 21 Aug
found 1 day ago
Return direct flight included
London (LGW) to New York (JFK)
9.4/10 Exceptional! (1,828 reviews)
Excelente atención al cliente

Reviewed on 3 Jul 2026

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
Price was £3,766, price is now £2,244 per person
£2,244
per person
14 Sept - 19 Sept
found 1 day ago
Return direct flight included
London (LHR) to New York (JFK)
9/10 Wonderful! (1,003 reviews)
5 star perfect place

Reviewed on 2 Jul 2026

Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Save 100% on your flight
Price was £2,363, price is now £1,443 per person
£1,443
per person
19 Sept - 26 Sept
found 13 hours ago
Return direct flight included
London (LGW) to Newark Liberty Intl. Airport (EWR)
7.4/10 Good! (3,239 reviews)
If you want a clean, perfectly functional and surprisingly "cheap" (considering it's New York, that is) hotel room, and you are planning to do most of your sightseeing from the Upper West Side, then you can't beat New York Night Hotel. It also has a history, formerly know as The Monterey Hotel.

Reviewed on 4 Jul 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was £2,733, price is now £1,675 per person
£1,675
per person
11 Sept - 14 Sept
found 1 day ago
Return flight included
Manchester (MAN) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
Atmosphere was amazing. Layout was incredibly unique. Will definitely be returning

Reviewed on 2 Jul 2026

The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
Save 100% on your flight
Price was £2,913, price is now £1,864 per person
£1,864
per person
19 Sept - 26 Sept
found 9 hours ago
Return flight included
London (LON) to New York (JFK)
8.8/10 Excellent! (618 reviews)
Really fabulous location, clean comfortable and spacious room. Nice continental breakfast, easy onsite parking and very helpful and friendly staff. Would absolutely stay again.

Reviewed on 1 Jul 2026

Shelter Island Heights Beach Holiday

Forget the stresses of daily life and let your mind, body and soul completely relax during your Shelter Island Heights holiday. There's nothing more invigorating than the cool sea breeze and the sound of waves crashing onto the shore. Organise your trip to Shelter Island Heights the quick and easy way by locking in one of our Shelter Island Heights packages. Many people opt to stay near Crescent Beach, a must-see only 1 mile from the city centre.

Shelter Island Heights Essential Information

Language
English
Currency
U.S dollars
Population
1,050
Max Temp Winter
4ºC
Max Temp Summer
24ºC
Top Sights
Wolffer Estates Vineyard, 67 Steps Beach and Kontokosta Winery

Top hotels in Shelter Island Heights

The Pridwin Hotel

The Pridwin Hotel

4 out of 5
81 Shore Road Shelter Island Heights NY
The price is £708 per night from 3 Aug to 4 Aug
£708
3 Aug - 4 Aug
includes taxes & fees
9.6/10 Exceptional! (90 reviews)
"Good service good people"

Reviewed on 27 Jun 2026

The Pridwin Hotel
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
8.4/10 Very good! (817 reviews)
"Beautiful room and location!"

Reviewed on 1 Jul 2026

Get rates
Gurney's Montauk Resort & Seawater Spa
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundable
The price is £80 per night from 9 Jul to 10 Jul
£80
9 Jul - 10 Jul
includes taxes & fees
8/10 Very good! (1,005 reviews)
"While the staff were very friendly and helpful. The property itself was like strolling back into 1980. It was not at all what I was expecting to find upon my arrival. Things were clean enough, but very outdated. I will say that the bed was actually very comfortable. The impression I gathered from ..."

Reviewed on 3 Jul 2026

Pier Blue Inn Old Saybrook - Essex
See all 4,783 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.
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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

Frequently asked questions

How much does a Shelter Island Heights travel package cost?
We make it simple to explore the world, with Shelter Island Heights packages starting from just £933. You'll have the flexibility to combine your favourite hotels, airlines and car rental. For the ultimate getaway, why not add a few tours and experiences to your itinerary?
If I'm not able to travel, can I cancel my Shelter Island Heights travel package?
Plans can change unexpectedly, so yes, you can. You may be able to cancel or alter your Shelter Island Heights travel package at no cost if you've booked in the last 24 hours. For older bookings, you can still make changes, but your car rental company, hotel or airline may impose a fee. Need more information? Take a look at our Customer Service Portal. We'll help make sure your getaway goes off without a hitch.
How do I get a cheap travel package to Shelter Island Heights?
If you love amazing deals, bundle your bookings into a Shelter Island Heights travel package. Whether you're looking for flights, hotels, rental cars or tours, you can book everything in one place. You'll have ample choice at your fingertips too. Expedia has over 550 air carriers and 1,000,000 hotel options around the globe to pick from. Fly with who you want, find a room where you like and save precious money — now that's the perfect getaway!
Does Expedia offer Book Now, Pay Later Shelter Island Heights holidays?
We sure do. Expedia has partnered with online lender Klarna to help you easily pay for your trip in instalments. Simply choose the payment plan that works for you during checkout and take away the stress of budgeting for your trip. Remember to bundle your flights, car hire and hotel with Expedia to get the biggest bang for your buck. Take a look at our flexible payment options below:

  • Pay monthly holidays: Make your holiday dreams a reality sooner with Klarna's manageable monthly instalment plans. If making small repayments each month works for you, choose this option during the checkout process.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay off your trip over multiple transactions.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the total upfront) makes it easier to click that "book now" button, choose a low deposit holiday payment plan with Klarna.

Where should I stay in Shelter Island Heights?
With lots to explore in Shelter Island Heights, we recommend you lock in a hotel close to its attractions. Sylvester Manor, Havens House and Mashomack Preserve are some interesting ones to put on your must-see list.
What are the top hotels in Shelter Island Heights?
One of the top places to stay in Shelter Island Heights is House On Chase Creek, in the Heights area. Explore the city by day and then rest your head in this comfortable hotel come nightfall.
How far in advance should I book my Shelter Island Heights holiday?
It can be hard to know exactly when is the perfect time to book your Shelter Island Heights trip. But generally the earlier you book, the more affordable the prices. Sometimes, you can lock in your flights and hotels up to a year before your departure date. If you're thinking of a last-minute getaway, no need to stress! There are unbeatable deals announced on Expedia every day.
What does an Expedia Shelter Island Heights travel package include?
Flights, rental cars and hotels — we have them well covered. With Expedia, you can shape your Shelter Island Heights package the way you want. All you have to do is figure out exactly what you need. Once you've made your booking, you can add on extras like activities and tours. The more you bundle, the bigger your savings!
What should I know before booking a Shelter Island Heights travel package?
So many places to go, so many things to do. With a travel package, you can cross more of them off your list. Combine your flights, rental cars and hotels and land big savings.
Can I choose my airline with a Shelter Island Heights Expedia travel package?
Most definitely. Expedia has access to more than 550 partner airlines across the globe, so you can tailor your Shelter Island Heights getaway according to your travel needs.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.