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.
Seven Beach Lane
CA $1,535
per person
Oct 4 - Oct 10
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.4/10 Exceptional! (32 reviews)
This hotel is in a great location close to town and restaurants. The rooms are well appointed and clean. The rooms by the pool are larger than the rooms in the house. We have stayed in both and I prefer the pool rooms although louder than the others. Nice pool and restaurant/bar on site. There is also a hotel shuttle to the beach and they were nice enough to drive us to dinner also.
Reviewed on Aug 21, 2026
The Plaza, A Fairmont Hotel
Manhattan
CA $3,814
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,001 reviews)
Everything was fantastic and consistent with our prior experience at the plaza. Check-in was fast, the room was spotless, room service was quick, turn Service down was nice to have. Food offerings are a little limited after 10:30 am, but you’re in Manhattan and can step outside and go 10 feet to any number of great restaurants.
Reviewed on Aug 24, 2026
Ready to book your vacation to Sheffield Island?
Sheffield Island Hotel Deals
Sonesta White Plains Downtown
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
CA $257
CA $340 total
Sep 6 - Sep 7
includes taxes & fees
Hyatt Regency Greenwich
1800 E Putnam Avenue Old Greenwich CT
Fully refundableReserve now, pay when you stay
CA $261
CA $300 total
Sep 20 - Sep 21
includes taxes & fees
8.8/10 Excellent! (1,125 reviews)
"Beautiful place! Charging for parking is absolutely ridiculous considering the price of the rooms. Charging for everything actually. No coffee, no breakfast, and the restaurant was very slow and expensive."
Reviewed on Aug 24, 2026
East Norwich Inn
6321 Northern Blvd. East Norwich NY
CA $145
CA $167 total
Aug 30 - Aug 31
includes taxes & fees
8/10 Very good! (1,871 reviews)
"Used to offer breakfast. Price is too high."
Reviewed on Aug 24, 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 CA $1,235 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.
