Sheffield Island Vacations from ￥535,337
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 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
The Latest Sheffield Island Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Find the Best Sheffield Island Vacation Packages
Sheffield Island Hotel Deals
Radisson Hotel Hauppauge-Long Island
110 Vanderbilt Motor Pkwy Hauppauge NY
Fully refundable
￥18,766
￥21,441 total
Sep 21 - Sep 22
includes taxes & fees
6.6/10 (1,784 reviews)
"Room was very clean"
Reviewed on Sep 11, 2026
Trumbull Marriott Shelton
180 Hawley Ln Trumbull CT
Fully refundableReserve now, pay when you stay
￥23,467
￥26,987 total
Sep 20 - Sep 21
includes taxes & fees
Sonesta White Plains Downtown
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
￥24,494
￥33,137 total
Oct 4 - Oct 5
includes taxes & fees
8.8/10 Excellent! (1,362 reviews)
"I walked into a magnificent lobby that was brightly lit and spacious. Room service was great and the mall across the street has a lovely food court. My room was comfy, roomy and spotless! A 10 out of 10 for me!"
Reviewed on Sep 9, 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 stop at Sheffield Island Lighthouse. Savor the top-notch restaurants and lively bars while in town.
Frequently asked questions
How much does a Sheffield Island vacation package cost?
You'll find cheap prices from ￥535,337 on Expedia for your Sheffield Island getaway. However, factors like the hotel choice, length of stay and season will determine how much your vacation 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 vacation 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 vacation 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 personalize your search by "Amenities," "Property type," "Traveler 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 vacation as a package?
You can enjoy significant savings on your Sheffield Island retreat by booking a customized vacation 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 vacation package to Sheffield Island?
If you're planning a spur-of-the-moment Sheffield Island vacation, 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 favorite season and the type of activities available will also help you decide when to vacation 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 vacation. 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 vacation 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.
