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.
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was CA $2,359, price is now CA $1,501 per person
CA $1,501
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (2,253 reviews)
Great hotel. Comfortable and great location. Staff a bit mixed. Some seemed stressed and receptionist seemed irritated when I asked questions on room availability. Breakfast staff also seemed stressed so staff werent really going out of their way (outside of the porters who helped with luggage).

Reviewed on Jul 18, 2026

Mandarin Oriental, New York

Mandarin Oriental, New York

5 out of 5
Manhattan
Price was CA $2,831, price is now CA $1,714 per person
CA $1,714
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (651 reviews)
Amazing hotel, staff make the whole experience, bar is great. Reception and concierge team are excellent, in particular Lauren who made check in a breeze. Gym and pool are excellent for a New York hotel.

Reviewed on Jun 21, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $5,893, price is now CA $3,744 per person
CA $3,744
per person
Sep 19 - Sep 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,006 reviews)

Hampton Inn Madison Square Garden Area Hotel

Hampton Inn Madison Square Garden Area Hotel

3 out of 5
Manhattan
Price was CA $3,515, price is now CA $2,236 per person
CA $2,236
per person
Sep 12 - Sep 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.2/10 Very good! (1,515 reviews)

San Carlos Hotel

San Carlos Hotel

4.5 out of 5
Manhattan
Price was CA $2,517, price is now CA $1,611 per person
CA $1,611
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (1,821 reviews)
Very respectful and courteous staff. Great experience!

Reviewed on Jul 17, 2026

Ready to book your vacation to Sheffield Island?

 

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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 CA $229 per night from Aug 16 to Aug 17
CA $229
CA $309 total
Aug 16 - Aug 17
includes taxes & fees
8.8/10 Excellent! (1,323 reviews)
"x"

Reviewed on Jul 17, 2026

Sonesta White Plains Downtown
Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
1800 E Putnam Avenue Old Greenwich CT
The price is CA $273 per night from Aug 18 to Aug 19
CA $273
CA $314 total
Aug 18 - Aug 19
includes taxes & fees
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 CA $143 per night from Aug 2 to Aug 3
CA $143
CA $164 total
Aug 2 - Aug 3
includes taxes & fees
6.6/10 (1,552 reviews)
"only ok"

Reviewed on Jul 18, 2026

La Quinta Inn & Suites by Wyndham Stamford / New York City
See all 1,013 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.
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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 from CA $1,501 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.

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