Sheffield Island Vacations from $377

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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.
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Manhattan
Price was $839, price is now $377 per person
$377
per person
Feb 20 - Feb 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.4/10 Good! (5,413 reviews)
I arrived at the hotel at about 130pm and saw a large cue for the front desk check in. I was in line for about 1 hr and a bit until i got to the desk and got served. Overall the hotel was okay. Convenient to our needs. I was very disappointed about the hotel not having coffee after 4pm at the hotel bar area. The whole area was apparently under renovation so not sure if this was the reason. We had asked for a kettle for the room but the desk said they don't have that so that was unfortunate. Overall the stay was okay for a quick stay in nyc.

Reviewed on Jan 9, 2026

Topping Rose House

Topping Rose House

4.5 out of 5
Price was $1,702, price is now $776 per person
$776
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
9.2/10 Wonderful! (136 reviews)
Great rooms, staff and food

Reviewed on Sep 28, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was $1,103, price is now $533 per person
$533
per person
Feb 20 - Feb 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (2,008 reviews)
The hospitality and customer service is top tier. The ambiance is modern, clean, and the city view was incredible of the Empire State Building.Our family loves staying at the various Melia hotels.

Reviewed on Jan 8, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was $3,083, price is now $1,538 per person
$1,538
per person
Mar 20 - Mar 25
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New Haven (HVN)
No reviews
Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
Price was $1,143, price is now $631 per person
$631
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (2,346 reviews)
Close to everything. ! Clean room! And nice staff!

Reviewed on Jan 5, 2026

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Discover the most popular places to visit in Sheffield Island

A nice spot for a picnic and a stroll along the beach.

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

EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
426 Main Ave, Route 7 Norwalk CT
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $128 total per night from Feb 9 to Feb 10
$128 total
Feb 9 - Feb 10
Total with taxes and fees
8.2/10 Very Good! (1,046 reviews)
I stay here every month I come to CT--safe, great bed, great staff, reliable and not expensive--what more can you want?

Reviewed on Jan 5, 2026

EVEN Hotel Norwalk by IHG
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
$179 nightly
The price is $205 total per night from Feb 8 to Feb 9
$205 total
Feb 8 - Feb 9
Total with taxes and fees
8.6/10 Excellent! (1,208 reviews)
Clean room, very helpful staff, resturant

Reviewed on Jan 5, 2026

Sonesta White Plains Downtown
DoubleTree by Hilton Stamford

DoubleTree by Hilton Stamford

3.5 out of 5
1 First Stamford Pl Stamford CT
Fully refundableReserve now, pay when you stay
$136 nightly
The price is $156 total per night from Jan 18 to Jan 19
$156 total
Jan 18 - Jan 19
Total with taxes and fees
7.4/10 Good! (1,015 reviews)
The customer service was absolutely amazing

Reviewed on Jan 4, 2026

DoubleTree by Hilton Stamford
See all 1,029 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 $377 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.