Sheffield Island Vacations

Book a Hotel + Flight together to unlock savings

Photo by Richard Miska

  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place

Find the Best Sheffield Island Vacation Packages

Sheffield Island Hotel Deals

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 SARĀ 668 per night from Jul 26 to Jul 27
SARĀ 668
SARĀ 889 total
26 Jul - 27 Jul
includes taxes & fees
Sonesta White Plains Downtown
Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
1800 E Putnam Avenue Old Greenwich CT
The price is SARĀ 781 per night from Aug 11 to Aug 12
SARĀ 781
SARĀ 898 total
11 Aug - 12 Aug
includes taxes & fees
8.6/10 Excellent! (1,077 reviews)
"clean room and excellent staff, good restaurants and common areas"

Reviewed on 19 July 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 SARĀ 380 per night from Aug 2 to Aug 3
SARĀ 380
SARĀ 437 total
2 Aug - 3 Aug
includes taxes & fees
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 length of stay, the season and your choice of hotel will influence how much your vacation to Sheffield Island costs.
What are the cheapest months to go to Sheffield Island?
You can usually find reduced prices and greater availability in January, February and March. Explore our cheap Sheffield Island vacation packages and you could score some great off-season discounts.
How to find the best Sheffield Island package deals?
Use Expedia's handy filters to help you find some terrific Sheffield Island package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or look for Sheffield Island package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Sheffield Island vacation as a package?
You can enjoy significant savings on your next Sheffield Island getaway by booking a personalized vacation package. Check the "Package" heading, then enter your destination and travel dates to see the best airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Sheffield Island?
Score amazing discounts by reserving your flights early with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Sheffield Island adventure.
How to plan a trip to Sheffield Island?

  1. Choose when to travel: Check your schedule and get packing. Your favorite season and the available activities will also help you decide when to escape to Sheffield Island.
  2. Work out your budget: Make sure you have enough money to pay for everything from transportation and meals to activities and flights. Your hotel will likely be the largest expense during your trip to Sheffield Island.
  3. Decide how long to go for: Now that you're up to speed on Sheffield Island, you can figure out the right length of your break. Create a rough itinerary and give yourself enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a customized Sheffield Island vacation package.