Sheffield Island Holidays

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Photo by Richard Miska

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    Save up to Rp16.000.000 when you book a flight and hotel together*

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Top hotels in Sheffield Island

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 Rp3.339.072 per night from 3 Jul to 4 Jul
Rp3.339.072
Rp4.414.532 total
3 Jul - 4 Jul
includes taxes & fees
8.8/10 Excellent! (1,324 reviews)
"Beautifully clean and comfortable"

Reviewed on 1 Jul 2026

Sonesta White Plains Downtown
Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
1800 E Putnam Avenue Old Greenwich CT
Fully refundableReserve now, pay when you stay
The price is Rp3.967.392 per night from 26 Jul to 27 Jul
Rp3.967.392
Rp4.562.501 total
26 Jul - 27 Jul
includes taxes & fees
8.6/10 Excellent! (1,041 reviews)
"Book this Hyatt hotel, you’ll be happy you did. Everything is great including the food and accommodations to the people who work there. Excellent."

Reviewed on 30 Jun 2026

Hyatt Regency Greenwich
La Quinta Inn & Suites by Wyndham Stamford / New York City

La Quinta Inn & Suites by Wyndham Stamford / New York City

3 out of 5
135 Harvard Avenue Stamford CT
Fully refundableReserve now, pay when you stay
The price is Rp1.841.875 per night from 5 Jul to 6 Jul
Rp1.841.875
Rp2.118.156 total
5 Jul - 6 Jul
includes taxes & fees
6.6/10 (1,498 reviews)
"Me encanta que es una estancia tranquila,no se escucha ruido se duerme cómodo delicioso.un personal amable y presto a hacer tu estancia agradable. Me encanta que es una estancia tranquila, no se escucha ruido se duerme cómodo delicioso.un personal amable y presto a hacer tu estancia. I love that ..."

Reviewed on 2 Jul 2026

La Quinta Inn & Suites by Wyndham Stamford / New York City
See all 1,003 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.

Stay near popular Sheffield Island attractions

Sheffield Island Lighthouse

8.8/10 (15 reviews)
You can learn about the history of Sheffield Island with a trip to Sheffield Island Lighthouse. Savour the top-notch restaurants and lively bars while in town.
See properties

Frequently asked questions

How much does a Sheffield Island holiday package cost?
You'll find cheap prices 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.

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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.