Sheffield Island Vacations from $655
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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.
The Latest Sheffield Island vacation packages
Price found within the past 48 hours. Click for updated prices.
Night Hotel Broadway
Manhattan
$655
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.6/10 Good! (3,584 reviews)
This is an old hotel in NYC, so it has small rooms and is a bit funky but we really liked it. The rooms were clean. There was a pedestal sink in the bathroom (nice tile) so they had added a shelf for toiletries. The hot water was was a bit slow getting to the the 12th floor but it warmed up pretty quickly. The wall outlets were old and too loose for a phone charger but there was a charging station on the desk that works beautifully. The staff was extremely helpful and really seemed to want to make sure guests enjoyed their stay. The location is great. You can easily go to 96th street and catch a crosstown bus or an subway to go down or uptown. We would definitely consider staying there again.
Reviewed on Sep 23, 2026
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View all tripsStay 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.
Sheffield Island Hotel Deals
Radisson Hotel Hauppauge-Long Island
110 Vanderbilt Motor Pkwy Hauppauge NY
Fully refundable
$135 nightly
$154 total
Oct 4 - Oct 5
Total with taxes and fees
6.6/10 (1,820 reviews)
"Overall decent stay. No frills, but comfy bed. There was an issue with my bathtub where the knob had to be replaced of which it was quickly done without any issues. Staff were friendly enough, but it is an older dated property. I would stay again if necessary."
Reviewed on Sep 23, 2026
Amsterdam Hotel
19 Clarks Hill Ave Stamford CT
Fully refundableReserve now, pay when you stay
$98 nightly
$113 total
Oct 24 - Oct 25
Total with taxes and fees
8.4/10 Very Good! (1,781 reviews)
"This is not fancy but a good value. The location is good and there's easy parking - a real bonus. Very easy in and out."
Reviewed on Sep 23, 2026
Sonesta White Plains Downtown
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
$218 nightly
$249 total
Oct 25 - Oct 26
Total with taxes and fees
8.8/10 Excellent! (1,347 reviews)
"The room was very clean and the staff were very helpful."
Reviewed on Sep 22, 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.
Find the Best Sheffield Island Vacation Packages
Sheffield Island Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | LaGuardia Airport (LGA) |
Top Sights | Jennings Beach, Norwalk Maritime Aquarium and Compo Beach |
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Frequently asked questions
How much does a Sheffield Island vacation package cost?
You'll find cheap prices from $655 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?
If you're looking to snag a cheap Sheffield Island vacation package, consider planning a trip in December, January and February. You're likely to find lower prices on flights and accommodations during these months — perfect for a budget-friendly getaway.
How many days is enough for Sheffield Island?
The ideal duration for your Sheffield Island vacation depends on what you'd like to see. Usually, a handful of days to a week will give you plenty of time to hit all the leading sights and explore some hidden spots along the way.
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.
Does Expedia offer Book Now, Pay Later Sheffield Island vacation packages?
If you're like us, you love exploring new places but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Sheffield Island vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
