Sheffield Island Vacations from $635

Book a Hotel + Flight or Car together to unlock savings

Photo by Richard Miska

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.
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $1,082, price is now $635 per person
$635
per person
Jan 22 - Jan 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,004 reviews)
Incredible views, ambiance, staff, and overall experience! The only thing to note is that it can be quite loud since you're right on the waterfront and the ferries and boats sound their horns frequently

Reviewed on Nov 8, 2026

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was $2,615, price is now $1,457 per person
$1,457
per person
Jan 10 - Jan 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was $1,467, price is now $830 per person
$830
per person
Jan 10 - Jan 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)
Everyone of the staff members where wonderful. Very busy front desk but efficient. The hotel is very nice and thoughtfully thought out.

Reviewed on Nov 9, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was $1,372, price is now $783 per person
$783
per person
Jan 10 - Jan 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (3,435 reviews)
My second time staying here and it never disappoints. Very clean, comfortable and attentive staff.

Reviewed on Nov 9, 2026

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Price was $2,547, price is now $1,503 per person
$1,503
per person
Jan 16 - Jan 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)

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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 top-notch restaurants and lively bars while in town.
See properties

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
$122 nightly
The price is $140 total per night from Nov 22 to Nov 23
$140 total
Nov 22 - Nov 23
Total with taxes and 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
$203 nightly
The price is $234 total per night from Nov 22 to Nov 23
$234 total
Nov 22 - Nov 23
Total with taxes and fees
8.8/10 Excellent! (1,218 reviews)
"If you want to be woken up on a Sunday at 6:00am with music, this is your place. If you want to sleep in, maybe go somewhere else"

Reviewed on Nov 9, 2026

Hyatt Regency Greenwich
East Norwich Inn

East Norwich Inn

2.5 out of 5
6321 Northern Blvd. East Norwich NY
$156 nightly
The price is $174 total per night from Nov 10 to Nov 11
$174 total
Nov 10 - Nov 11
Total with taxes and fees
8/10 Very Good! (1,819 reviews)
"Nice place with character in a good neighborhood. Would stay here again."

Reviewed on Nov 9, 2026

East Norwich Inn
See all 984 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.

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 $635 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.