Sheffield Island Holidays from AU$3,575

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Your Sheffield Island Holiday

A great way to experience this city is with a customised Sheffield Island holiday package. Base yourself in the neighbourhood of Downtown Stamford, which is great for history, bars and pubs and dining or go someplace else — our packages are all about you. Every trip to Sheffield Island needs a well-designed itinerary. Fill yours with big-name attractions like Compo Beach, Chelsea Piers and Norwalk Maritime Aquarium. Check out Expedia's wide range of travel options and start planning your perfect holiday to Sheffield Island now.

The Latest Sheffield Island Holiday Deals

Price found within the past 48 hours. Click for updated prices.
The Benjamin Royal Sonesta New York

The Benjamin Royal Sonesta New York

4.5 out of 5
Manhattan
per person
8 Sept - 15 Sept
found 1 hour ago
Return direct flight included
Sydney (SYD) to New York (JFK)
8.6/10 Excellent! (1,011 reviews)
Great room , a lot of good places to eat nearby

Reviewed on 5 Aug. 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
per person
8 Sept - 15 Sept
found 1 hour ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.2/10 Wonderful! (1,000 reviews)
Exceedingly above my expectations

Reviewed on 31 Jul. 2025

Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
per person
12 Sept - 19 Sept
found 20 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
8/10 Very Good! (2,135 reviews)
A good hotel to stay at which was convenient for a holiday in New York. Walkable distance to main attractions.

Reviewed on 7 Aug. 2025

Baccarat Hotel and Residences New York

Baccarat Hotel and Residences New York

5 out of 5
Manhattan
Save 100% on your flight
per person
8 Sept - 15 Sept
found 1 hour ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.4/10 Exceptional! (469 reviews)
Luxurious restaurant

Reviewed on 4 Aug. 2025

Concorde Hotel New York

Concorde Hotel New York

4 out of 5
Manhattan
per person
8 Sept - 15 Sept
found 1 hour ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9/10 Wonderful! (1,007 reviews)
One of my favorite place to stay highly recommended

Reviewed on 3 Aug. 2025

Sheffield Island Holiday

Sheffield Island Essential Information

Language
English
Currency
U.S dollars
Closest Airport
LaGuardia Airport (LGA)
Top Sights
Compo Beach, Norwalk Maritime Aquarium and Jennings Beach

Our pick of the best Sheffield Island Hotel Deals

Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

4 out of 5
99 East Avenue, Norwalk, CT
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (1,265 reviews)
"We loved staying at the Norwalk Inn. It was a delight. Facilities are beautiful, and the location is top-notch."

Reviewed on 6 Aug. 2025

Get rates
Norwalk Inn & Conference Center
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
66 Hale Ave, White Plains, NY
Fully refundableReserve now, pay when you stay
The price is AU$322 per night from 1 Sept to 2 Sept
AU$322
1 Sept - 2 Sept
includes taxes & fees
8.6/10 Excellent! (1,097 reviews)
"Everything was fantastic bed was super comfy. Great room service. Only issue, one of the pool attendants vomited into a poolside waste paper basket as I started swimming around 9pm night before I checked out, he left it there said nothing then rested on the job, I immediately went to my room. In ..."

Reviewed on 3 Aug. 2025

Sonesta White Plains Downtown
Amsterdam Hotel

Amsterdam Hotel

2 out of 5
19 Clarks Hill Ave, Stamford, CT
Fully refundableReserve now, pay when you stay
8.4/10 Very Good! (1,628 reviews)
"Nice place @ a good price"

Reviewed on 5 Aug. 2025

Get rates
Amsterdam Hotel
See all 968 properties in Sheffield Island
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.
All Inclusive Holidays
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Beach Holidays

Frequently asked questions

How much does a Sheffield Island holiday package cost?
You'll find cheap prices from AU$3,575 on Expedia for your Sheffield Island getaway. However, factors like the hotel choice, length of stay and season will determine how much your holiday to Sheffield Island costs.
What are the cheapest months to go to Sheffield Island?
January, February and March are great times to search for cheap Sheffield Island holiday packages. Choosing to travel in less busy months means you can usually find lower prices on flights and hotels.
How many days is enough for Sheffield Island?
The ideal duration for your Sheffield Island holiday depends on what you'd like to do. Usually, a few days to a week will give you plenty of time to tick off all the leading sights and discover some hidden gems along the way.
How to find the best Sheffield Island package deals?
Finding a cheap Sheffield Island package deal is a breeze with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can personalise your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Sheffield Island package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Sheffield Island holiday as a package?
You can enjoy significant savings on your Sheffield Island retreat by booking a customised holiday package. Click on the "Package" heading, then select your destination and travel dates to see some great flight and hotel prices. Bundle everything into a great-value 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 Sheffield Island?
If you're planning a spur-of-the-moment Sheffield Island holiday, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can land terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Sheffield Island?

  1. Choose when to travel: Check your schedule and pack your bags. Your favourite season and the type of activities available will also help you decide when to holiday in Sheffield Island.
  2. Calculate your budget: Make sure you have enough money to cover everything from transportation and food to experiences and flights. Your hotel will probably be the largest expense during your trip to Sheffield Island.
  3. Decide how long to go away for: Now that you're more familiar with Sheffield Island, you can work out the right length of your holiday. Pull together a rough plan and allocate enough time to cover everything you want to do.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to choose a Sheffield Island holiday package that brings all your bookings together.

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