Sheffield Island Vacations from $375

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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.
Newark Liberty International Airport Marriott

Newark Liberty International Airport Marriott

4 out of 5
Save 100% on your flight
Price was $628, price is now $375 per person
$375
per person
May 30 - Jun 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (1,005 reviews)
Great service and location.

Reviewed on Apr 11, 2026

Delta Hotels by Marriott Woodbridge

Delta Hotels by Marriott Woodbridge

4 out of 5
Save 100% on your flight
Price was $874, price is now $458 per person
$458
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,002 reviews)
Front desk person was very unfriendly and uninterested.

Reviewed on Apr 9, 2026

New York Marriott Marquis

New York Marriott Marquis

4.5 out of 5
Manhattan
Price was $1,549, price is now $834 per person
$834
per person
Jun 30 - Jul 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (4,338 reviews)
The hotel was very difficult to navigate which added a lot of stress to our stay. The rooms were clean but very basic in my opinion for this price range. Overall we were comfortable in the room and had a good trip but probably wouldn’t stay here again

Reviewed on Apr 13, 2026

Seven Beach Lane

Seven Beach Lane

2 out of 5
Save 100% on your flight
Price was $2,018, price is now $1,117 per person
$1,117
per person
Jun 1 - Jun 3
just found
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
10/10 Exceptional! (6 reviews)
Courteous and friendly staff

Reviewed on Nov 4, 2025

Candlewood Suites New York City-Times Square by IHG

Candlewood Suites New York City-Times Square by IHG

2.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,189, price is now $706 per person
$706
per person
May 14 - May 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (1,827 reviews)
The studio suite was clean and met our need.

Reviewed on Apr 12, 2026

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Discover the most popular places to visit in Sheffield Island

Sheffield Island Lighthouse

Sheffield Island Lighthouse

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.

Sheffield Island Lighthouse

Sheffield Island Hotel Deals

Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln Trumbull CT
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $175 total per night from Apr 26 to Apr 27
$175 total
Apr 26 - Apr 27
Total with taxes and fees
8/10 Very Good! (1,010 reviews)
no hot tub. listing lied

Reviewed on Apr 13, 2026

Trumbull Marriott Shelton
East Norwich Inn

East Norwich Inn

2.5 out of 5
6321 Northern Blvd. East Norwich NY
$128 nightly
The price is $143 total per night from Apr 14 to Apr 15
$143 total
Apr 14 - Apr 15
Total with taxes and fees
8/10 Very Good! (1,839 reviews)
Worth it.

Reviewed on Apr 13, 2026

East Norwich Inn
Radisson Hotel Hauppauge-Long Island

Radisson Hotel Hauppauge-Long Island

3.5 out of 5
110 Vanderbilt Motor Pkwy Hauppauge NY
Fully refundable
$110 nightly
The price is $126 total per night from Apr 26 to Apr 27
$126 total
Apr 26 - Apr 27
Total with taxes and fees
6.4/10 (1,498 reviews)
Not good as it's looks, they don't provide breakfast, in the hallway it's smell ad they charge me extra for checking out at 11:30 i know every hotel u should leave at 12PM

Reviewed on Apr 13, 2026

Radisson Hotel Hauppauge-Long Island
See all 1,034 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 $375 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.