Sheffield Island Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to Rp16.000.000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Sheffield Island
Sonesta White Plains Downtown
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
Rp2.963.739
Rp3.981.097 total
6 Sept - 7 Sept
includes taxes & fees
8.8/10 Excellent! (1,357 reviews)
"Disappointed that they only offered Starbucks Coffee and Pepsi products."
Reviewed on 17 Aug 2026
Hyatt Regency Greenwich
1800 E Putnam Avenue Old Greenwich CT
Fully refundableReserve now, pay when you stay
Rp3.212.425
Rp3.694.289 total
6 Sept - 7 Sept
includes taxes & fees
8.8/10 Excellent! (1,105 reviews)
"This was our second stay, a year after our first one. The property is very clean. If you order room service, it is delivered right on time that it says it will be delivered. All staff appear genuinely friendly and helpful. The pool is wonderful. We even tried the movie theater this time and it was ..."
Reviewed on 16 Aug 2026
East Norwich Inn
6321 Northern Blvd. East Norwich NY
Rp1.975.888
Rp2.271.755 total
20 Aug - 21 Aug
includes taxes & fees
8/10 Very good! (1,857 reviews)
"Quaint Tudor style Inn - throw back to when Burt Bacharach owned it. Convenient to several good restaurants, and bagel/coffe shop, as well as a high end grocery store. He king bed and pillows were really comfy"
Reviewed on 17 Aug 2026
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.
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?
- 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.
- 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.
- 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.
- 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.
