Sheffield Island Vacations

Book a Hotel + Flight together to unlock savings

Photo by Richard Miska

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    Save up to AED 148 when you book a flight and hotel together*
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Find the Best Sheffield Island Vacation Packages

Sheffield Island Hotel Deals

EVEN Hotel Norwalk by IHG
EVEN Hotel Norwalk by IHG
3.5 out of 5
426 Main Ave, Route 7, Norwalk, CT
Fully refundable
The price is AED 400 per night from Jun 30 to Jul 1
AED 400
AED 460 total
30 Jun - 1 Jul
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Very clean room and bathroom, large shower and useful desk were highlights. Prepaid room type was not available and was given drink coupon at check in as a makeup."

Reviewed on 5 June 2025

EVEN Hotel Norwalk by IHG
Amsterdam Hotel
Amsterdam Hotel
2 out of 5
19 Clarks Hill Ave, Stamford, CT
Fully refundableReserve now, pay when you stay
The price is AED 316 per night from Jun 16 to Jun 17
AED 316
AED 367 total
16 Jun - 17 Jun
includes taxes & fees
8.4/10 Very Good! (1,589 reviews)
"The rooms were large and comfortable. Close off highway 95 and food available within walking distance. Very convenient."

Reviewed on 27 May 2025

Amsterdam Hotel
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 AED 621 per night from Jul 6 to Jul 7
AED 621
AED 714 total
6 Jul - 7 Jul
includes taxes & fees
8/10 Very Good! (929 reviews)
"Love the vibe! ♥️"

Reviewed on 3 June 2025

Hyatt Regency Greenwich
See all 957 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.

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 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.

Discover the most popular places to visit in Sheffield Island

A nice spot for a picnic and a stroll along the beach.

Sheffield Island Lighthouse

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.

Sheffield Island Lighthouse