Sheffield Island Vacation Packages
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Your Sheffield Island Vacation
From its highlights to its hidden treasures, this city is best experienced with a Sheffield Island vacation package. Book a hotel in Downtown Stamford, which is good for history, bars and pubs and dining. If your trip to Sheffield Island includes a little sightseeing, check out much-loved attractions like Chelsea Piers, Norwalk Maritime Aquarium and Compo Beach. A couple of clicks is all it takes to put together a tailor-made Sheffield Island vacation on Expedia.
Top Sheffield Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The William Hotel Midtown, New York
Manhattan
CA $1,779
per person
Dec 4 - Dec 8
found 17 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.4/10 Exceptional! (232 reviews)
This was such a charming hotel and centrally located for what we had planned during our girls trip. The front desk staff was incredibly kind and helpful. The room was large, and the kitchenette was definitely a bonus. We felt safe and very well taken care of.
Reviewed on Sep 9, 2026
The High Line Hotel
Manhattan
CA $1,986
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to New York (JFK)
8.6/10 Excellent! (1,002 reviews)
I love boutique style’s hotels and this one checked all of the boxes. It was very charming, nicely decorated, and conveniently located. The building/property was one of my favorite details as well as the outdoor bar area which felt like I was in Europe, specifically in London because of a double decker UK bus that sat at the end of the bar garden as a decor. My only feedback to the hotel is that it’s time for some touch up work ie… repainting the walls in the room, replacing the velvet drapes and updating the bathroom (my sink worked fine but had a crack in it). Otherwise it was a great stay and the bed was very comfortable!
Reviewed on Sep 9, 2026
Hotel Riu Plaza New York Times Square
Manhattan
CA $2,414
per person
Dec 4 - Dec 8
found 17 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9/10 Wonderful! (3,331 reviews)
La espera de una habitación tardó más de lo normal eran las 4:45 y todavía seguimos esperando por la habitación 711 ya que teníamos 2 habitaciones una si fue entrega a las 3:20 y la otra de tardo más de 3 horas después, servicio muy bueno desayuno excelente personal excelente
Reviewed on Sep 9, 2026
Hotel AKA NoMad
Manhattan
CA $1,853
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,012 reviews)
Property was clean. It was very modern. The rooms were a bit dark for my taste. Room service was bad. I called for body wash. Never got it. Location was great.
Reviewed on Sep 10, 2026
Ready to book your vacation to Sheffield Island?
Sheffield Island Hotel Deals
Radisson Hotel Hauppauge-Long Island
110 Vanderbilt Motor Pkwy Hauppauge NY
Fully refundable
CA $169
CA $193 total
Sep 20 - Sep 21
includes taxes & fees
Trumbull Marriott Shelton
180 Hawley Ln Trumbull CT
Fully refundableReserve now, pay when you stay
CA $210
CA $241 total
Sep 20 - Sep 21
includes taxes & fees
8/10 Very good! (1,003 reviews)
"Everything was great I enjoyed all of my nights at the property"
Reviewed on Sep 9, 2026
Hyatt Regency Greenwich
1800 E Putnam Avenue Old Greenwich CT
Fully refundableReserve now, pay when you stay
CA $304
CA $349 total
Oct 4 - Oct 5
includes taxes & fees
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 CA $1,779 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 many days is enough for Sheffield Island?
With a well-planned schedule, you can easily tick off the top Sheffield Island sights in a few days. But if you'd like to discover hidden spots or go on day tours, think about booking your Sheffield Island vacation for longer.
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?
- Choose when to travel: Check your schedule and get packing. Your favourite season and the available activities will also help you decide when to escape to Sheffield Island.
- 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.
- 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.
- 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
