Sheffield Island Vacations

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    Save up to ₩1,660,000 when you book a flight and hotel together*

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Find the Best Sheffield Island Vacation Packages

Sheffield Island Hotel Deals

Radisson Hotel Hauppauge-Long Island

Radisson Hotel Hauppauge-Long Island

3.5 out of 5
110 Vanderbilt Motor Pkwy Hauppauge NY
The price is ₩248,876 per night from Jul 26 to Jul 27
₩248,876
₩284,341 total
Jul 26 - Jul 27
includes taxes & fees
6.4/10 (1,702 reviews)
"Just first room had a broken conditioner, moved rooms without a walkout which is what we requested in our Expedia booking the room that we were transferred to had a broken TV had a broken tv. We had to set our own alarm clocks and we were missing lightbulbs, and in both lamps moved to a third room ..."

Reviewed on Jul 20, 2026

Radisson Hotel Hauppauge-Long Island
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 ₩309,007 per night from Jul 26 to Jul 27
₩309,007
₩355,358 total
Jul 26 - Jul 27
includes taxes & fees
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 ₩159,678 per night from Aug 2 to Aug 3
₩159,678
₩183,630 total
Aug 2 - Aug 3
includes taxes & fees
6.6/10 (1,565 reviews)
"Rooms were dirty, construction debris everywhere. Would not recommend."

Reviewed on Jul 22, 2026

La Quinta Inn & Suites by Wyndham Stamford / New York City
See all 1,012 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 stop at Sheffield Island Lighthouse. Savor the lively bars and top-notch restaurants while in town.
See properties

Frequently asked questions

How much does a Sheffield Island vacation 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 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?

  1. 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.
  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 vacation. 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 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.