Sheffield Island Vacations from $364

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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.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $711, price is now $364 per person
$364
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
This place is the bomb. Loved our suite, loved the pool and the breakfast was wonderful

Reviewed on Aug 12, 2025

Harpoon House

Harpoon House

3 out of 5
Price was $941, price is now $494 per person
$494
per person
Oct 20 - Oct 24
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (125 reviews)
Lovely renovation with everything new and fresh. Just a couple of things missing like a bedside clock and a hair dryer, but a quite good accommodation within easy walking distance of town.

Reviewed on Aug 19, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $2,262, price is now $1,236 per person
$1,236
per person
Oct 26 - Oct 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,008 reviews)
Rooms are so nice and spacious. Plenty of room to enjoy indoor time. Lots of outdoor options on and near the property. Highly recommend. Beautiful views of the bridges and the city.

Reviewed on Aug 19, 2025

The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
Save 100% on your flight
Price was $934, price is now $543 per person
$543
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
8.8/10 Excellent! (495 reviews)
Great hotel. Staff were amazing! Loved that you could use their sister property by the beach and stay in town. Just did not like having to pay for overnight parking.

Reviewed on Aug 14, 2025

Hotel Beacon

Hotel Beacon

4 out of 5
Manhattan
Save 100% on your flight
Price was $3,148, price is now $1,841 per person
$1,841
per person
Sep 22 - Sep 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.4/10 Exceptional! (1,262 reviews)
Clean room. Comfortable bed. Staff is great. Went to show next door. Easy comfortable trip. Cafe next door was delicious.

Reviewed on Aug 17, 2025

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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

Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

4 out of 5
99 East Avenue, Norwalk, CT
Fully refundableReserve now, pay when you stay
$124 nightly
The price is $143 total per night from Aug 24 to Aug 25
$143 total
Aug 24 - Aug 25
Total includes taxes and fees
8.6/10 Excellent! (1,294 reviews)
"Great value for the money"

Reviewed on Aug 18, 2025

Norwalk Inn & Conference Center
Amsterdam Hotel

Amsterdam Hotel

2 out of 5
19 Clarks Hill Ave, Stamford, CT
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $116 total per night from Aug 20 to Aug 21
$116 total
Aug 20 - Aug 21
Total includes taxes and fees
8.4/10 Very Good! (1,642 reviews)
Good stay but could use a renovation!
"My partner and I stayed for one night here, we had a pleasant enough stay. Quick check in, plenty of parking. However the hotel clearly needs to be updated, it feels like the hotel is right out of the 90s. The bed was decently comfortable but I was glad we brought our own pillows. Definitely a good ..."

Reviewed on Aug 15, 2025

Amsterdam Hotel
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
$202 nightly
The price is $231 total per night from Sep 1 to Sep 2
$231 total
Sep 1 - Sep 2
Total includes taxes and fees
8.6/10 Excellent! (1,104 reviews)
"Excellent welcoming front desk staff!"

Reviewed on Aug 18, 2025

Sonesta White Plains Downtown
See all 968 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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Frequently asked questions

How much does a Sheffield Island vacation package cost?
You'll find cheap prices from $364 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.