Sheffield Island Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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

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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.
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Price was CA $1,617, price is now CA $1,017 per person
CA $1,017
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
7.6/10 Good! (3,805 reviews)

Luxury NY Home 3BR with Easy Parking

Luxury NY Home 3BR with Easy Parking

3 out of 5
Southeast Yonkers
Save 100% on your flight
Price was CA $5,063, price is now CA $3,151 per person
CA $3,151
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to White Plains (HPN)
3/10 (4 reviews)

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Save 100% on your flight
Price was CA $6,819, price is now CA $4,245 per person
CA $4,245
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to New York (JFK)
9.2/10 Wonderful! (706 reviews)

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
Price was CA $6,231, price is now CA $3,988 per person
CA $3,988
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
Great location; great service. Seemed to be a problem with the room heat/AC, but the weather was mild in NYC that week, so I cannot fully confirm.

Reviewed on Oct 26, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was CA $4,919, price is now CA $3,202 per person
CA $3,202
per person
Dec 2 - Dec 5
found 19 hours ago
Roundtrip flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)

Ready to book your vacation to Sheffield Island?

 

Choose your dates

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
Fully refundable
The price is CA $172 per night from Nov 15 to Nov 16
CA $172
CA $196 total
Nov 15 - Nov 16
includes taxes & fees
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 CA $275 per night from Nov 19 to Nov 20
CA $275
CA $316 total
Nov 19 - Nov 20
includes taxes & fees
8.8/10 Excellent! (1,193 reviews)
"I will definitely be back. such a great hotel. Especially love the lobby and staff; the rooms are super cute and cozy."

Reviewed on Oct 27, 2026

Hyatt Regency Greenwich
East Norwich Inn

East Norwich Inn

2.5 out of 5
6321 Northern Blvd. East Norwich NY
The price is CA $171 per night from Oct 29 to Oct 30
CA $171
CA $196 total
Oct 29 - Oct 30
includes taxes & fees
East Norwich Inn
See all 1,018 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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.
See properties

Frequently asked questions

How much does a Sheffield Island vacation package cost?
You'll find cheap prices from CA $1,017 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?

  1. 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.
  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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.