Sheffield Island Holidays from £867
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Your Sheffield Island Holiday
From its highlights to its hidden treasures, this city is best experienced with a Sheffield Island holiday 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 holiday on Expedia.
Top Sheffield Island Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
1 Hotel Brooklyn Bridge
£2,246
per person
16 Nov - 22 Nov
found 1 day ago
Return direct flight included
London (LON) to New York (JFK)
9/10 Wonderful! (1,013 reviews)
We flew in to attend the U.S. Open and stayed at 1 Hotel Brooklyn. The staff was warm, welcoming, and attentive throughout our stay. The views of Manhattan and the Brooklyn Bridge are truly hard to beat. We had a wonderful experience and would absolutely stay here again!
Reviewed on 5 Sept 2026
Sheffield Island Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | LaGuardia Airport (LGA) |
Top Sights | Norwalk Maritime Aquarium, Compo Beach and Jennings Beach |
Top hotels in Sheffield Island
Radisson Hotel Hauppauge-Long Island
110 Vanderbilt Motor Pkwy Hauppauge NY
Fully refundable
£103
13 Sept - 14 Sept
includes taxes & fees
6.6/10 (1,779 reviews)
"Work in progress abit dated. Staff can't complain they made up for what the hotel lacks"
Reviewed on 5 Sept 2026
Hyatt Regency Greenwich
1800 E Putnam Avenue Old Greenwich CT
£158
27 Sept - 28 Sept
includes taxes & fees
8.8/10 Excellent! (1,140 reviews)
"If you are looking to get some rest this is not the place. Got a hotel so we I could get some quiet and work, it was the opposite, a loud wedding sounded like banging all night until 1 am. I called front desk starting at 11pm and they never picked up. Finally called the Hyatt main line and they connected ..."
Reviewed on 6 Sept 2026
Trumbull Marriott Shelton
180 Hawley Ln Trumbull CT
Fully refundableReserve now, pay when you stay
£127
7 Sept - 8 Sept
includes taxes & fees
8/10 Very good! (1,005 reviews)
"I had a very peaceful stay... If I needed anything the staff made sure I had it right away. The hotel was clean and up to par..."
Reviewed on 6 Sept 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.
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 trip to Sheffield Island Lighthouse. Savour the top-notch restaurants and lively bars while in town.
Frequently asked questions
Why should I book my Sheffield Island holiday with Expedia?
With top-value airfares, car hire and hotel choices all in one place, Expedia makes booking your Sheffield Island getaway a piece of cake. Plus, we can help you bundle your bookings into a package holiday so you can get even more savings. Pick from fantastic retreats, add your flights and/or a hire car (and maybe also some exciting activities!) and land incredible prices. Want to change your plans? Expedia has a flexible cancellation policy for many bookings. To learn more, head over to our Customer Service Portal link.
How do I get a cheap holiday to Sheffield Island?
If you love amazing deals, bundle your bookings into a Sheffield Island holiday. Whether you're searching for flights, hotels, day tours or hire cars, you can browse and book everything in one place. You'll have lots of choice at your fingertips as well. Expedia has more than 400 partner airlines and 321,000 hotel options worldwide to take your pick of. Fly with who you prefer, book a room where you like and save precious pounds — now that's the ideal escape! Learn more about how you can save money on your next holiday when you combine your hotel and flight bookings with Expedia.
Do I need a visa for my Sheffield Island holiday?
Official government websites are the best source of information on visa requirements, application procedures and any supporting documentation. Your nationality and purpose for visiting, whether it be for tourism or work, will determine if you need a visa for Sheffield Island. Also make sure your passport is up to date and has a minimum of six months validity remaining after your return date. Finalise all your travel planning well in advance to avoid any last-minute surprises.
What should I wear on my Sheffield Island holiday?
Consider the type of activities planned during your holiday in Sheffield Island and create a travel wardrobe that you can easily mix and match. For fashion inspiration or even information on dress codes, look up a few style blogs or social media accounts.
What does an Expedia Sheffield Island holiday include?
Flights, hotels and a cool set of wheels for your road trip adventures. Simply choose your preferred bundle and get access to great discounts. Once you've made your booking, add on a couple of activities and tours and watch your savings stack up. When it comes to organising your Sheffield Island break, you're the one in control! Expedia gives you the flexibility and freedom to design the holiday you've always wanted, your way.
Does Expedia offer Book Now, Pay Later Sheffield Island holidays?
Expedia has partnered with online lender Klarna to make booking your next getaway a bit easier on the wallet. Paying in instalments means you can spread the costs of your next adventure, leaving you with more cash to spend while you're travelling. Klarna has several payment plans to choose from, so you're sure to find something that suits your budget. Browse these flexible payment options:
- Pay monthly holidays: If paying in multiple transactions sounds best for you, Klarna offers just that! Paying in convenient monthly instalments will make that dream getaway possible.
- No-deposit holidays: Pressing the "book now" button is easier with this payment option. With no upfront fee for your getaway, you can Book Now, Pay Later and start packing your bags.
Can I choose my airline with a Sheffield Island Expedia holiday?
Definitely. Expedia has more than 400 partner airlines to choose from around the globe. With all that choice at your fingertips, finding the ideal carrier to whisk you away to Sheffield Island will be easy.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
