Title: Sheffield Island Vacation Packages & Trips 2025/2026 from CA $850 | Expedia.ca

  

[Sheffield Island Travel Guide](https://expedia.ca/Sheffield-Island.dx6353650)[Hotels in Sheffield Island](https://expedia.ca/Sheffield-Island-Hotels.d6353650.Travel-Guide-Hotels)[Vacation Rentals in Sheffield Island](https://expedia.ca/Sheffield-Island-Vacation-Rentals.d6353650.Travel-Guide-VacationRentals)[Sheffield Island Car Rentals](https://expedia.ca/Car-Rentals-In-Sheffield-Island.d6353650.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium)

# Sheffield Island Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

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Better together

Save up to CA $1,096 when you book a flight and hotel together\*

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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](https://www.expedia.ca/Chelsea-Piers-Cove-East-Side-Shippan.d6247586.Vacation-Attraction), [Norwalk Maritime Aquarium](https://www.expedia.ca/Norwalk-Maritime-Aquarium-Norwalk.d6071501.Vacation-Attraction) and [Compo Beach](https://www.expedia.ca/Compo-Beach-Westport.d553248621532664563.Vacation-Attraction). A couple of clicks is all it takes to put together a tailor-made Sheffield Island vacation on Expedia.

## Top Sheffield Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.

![Hyatt Centric Times Square New York](https://images.trvl-media.com/lodging/7000000/6310000/6300700/6300652/614d4693_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hyatt Centric Times Square New York

Manhattan

CA $850

per person

Nov 14 - Nov 17

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to New York (JFK)

9.2/10 Wonderful! (1,866 reviews)

Good room size for new york, nice bathrooms and ideally located for Times square and the subway

Reviewed on Oct 1, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-17/?FromAirport=YHM&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6300652&paandie=true&dealMarker=yQQAUw-TgjVxJzqFcjthPoC4fpqub-GiXa51smxv3YJs0rT7kTiZGiybgMnNND7P)

![Courtyard New York Manhattan/ Midtown East](https://images.trvl-media.com/lodging/1000000/160000/151300/151297/9d70bdbc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Courtyard New York Manhattan/ Midtown East

Manhattan

CA $2,093

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9/10 Wonderful! (2,306 reviews)

Carpet are so dirty and bath tube no clean

Reviewed on Oct 2, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-07/?FromAirport=YTO&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=151297&paandie=true&dealMarker=6G4VshBxpt1VGdnGDnuoqohLVAcqJl31UWmCfraTx5UjqCXEyT_dlXRghhJIpE4B)

![NobleDEN Hotel](https://images.trvl-media.com/lodging/9000000/8690000/8682300/8682234/cb1dc844_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### NobleDEN Hotel

Manhattan

CA $1,428

per person

Nov 15 - Nov 20

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9.8/10 Exceptional! (1,344 reviews)

Great location, modern conveniences, and excellent staff

Reviewed on Sep 27, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-15/2025-11-20/?FromAirport=YTO&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=8682234&paandie=true&dealMarker=xey1eaOdfCcqi6ODbZdr9yMOFtPkYHgkn8NEV3tMcbEvE63wwh76Hadq47FNBomL)

![The Carlyle, A Rosewood Hotel](https://images.trvl-media.com/lodging/1000000/50000/40600/40553/f6335dcc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Carlyle, A Rosewood Hotel

Manhattan

CA $3,825

per person

Nov 27 - Nov 30

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9.4/10 Exceptional! (827 reviews)

Concierge even tied my husbands bow tie - wonderful stay!

Reviewed on Sep 27, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-27/2025-11-30/?FromAirport=YTO&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=40553&paandie=true&dealMarker=HGguCrQBXUPrD9iulwr_Cw_P3Gh9tHnrnh_B6JgZDDQzmYlAS_VW0Xe0ggK-jd3W)

![Night Hotel Broadway](https://images.trvl-media.com/lodging/1000000/130000/129400/129325/54f0bae9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Night Hotel Broadway

Manhattan

CA $1,015

per person

Dec 14 - Dec 19

found 24 hours ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

7/10 Good! (2,403 reviews)

The area is great, but the hotel itself is quite old and outdated. If you’re on a tight budget and need a place to stay, it’ll suffice, but don’t expect anything fancy.

Reviewed on Oct 3, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-14/2025-12-19/?FromAirport=YTO&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=129325&paandie=true&dealMarker=k3V8eBwNGTImMtO1tWx35eU9cUowwf-dWlyieALmdYdWEJXavNwN4YueDVI8xLNm)

## Ready to book your vacation to Sheffield Island?

Choose your dates

## Sheffield Island Hotel Deals

![Amsterdam Hotel](https://images.trvl-media.com/lodging/1000000/30000/20800/20793/f5bb9592_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Amsterdam Hotel

19 Clarks Hill Ave, Stamford, CT

Fully refundableReserve now, pay when you stay

CA $140

CA $162 total

Oct 7 - Oct 8

includes taxes & fees

8.4/10 Very Good! (1,690 reviews)

"N/A. Wi-Fi was adequate."

Reviewed on Sep 27, 2025

[](https://expedia.ca/Hotel-Search?startDate=07%2F10%2F2025&endDate=08%2F10%2F2025&selected=20793&PinnedHotelID=20793&HadPinnedHotel=true&regionId=6353650)

![Norwalk Inn & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/15200/15114/13ab5174_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Norwalk Inn & Conference Center

99 East Avenue, Norwalk, CT

Fully refundableReserve now, pay when you stay

CA $161

CA $186 total

Oct 26 - Oct 27

includes taxes & fees

8.6/10 Excellent! (1,320 reviews)

"Helpful and pleasant staff. Attractive property and location."

Reviewed on Sep 29, 2025

[](https://expedia.ca/Hotel-Search?startDate=26%2F10%2F2025&endDate=27%2F10%2F2025&selected=15114&PinnedHotelID=15114&HadPinnedHotel=true&regionId=6353650)

![La Quinta Inn & Suites by Wyndham Stamford / New York City](https://images.trvl-media.com/lodging/1000000/30000/25000/24963/af81668d_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

La Quinta Inn & Suites by Wyndham Stamford / New York City

135 Harvard Avenue, Stamford, CT

Fully refundableReserve now, pay when you stay

CA $115

CA $133 total

Oct 26 - Oct 27

includes taxes & fees

6.4/10 (843 reviews)

"The bed was terribly hard and the parking lot is not well designed but over all the place was nice and the price was great"

Reviewed on Sep 24, 2025

[](https://expedia.ca/Hotel-Search?startDate=26%2F10%2F2025&endDate=27%2F10%2F2025&selected=24963&PinnedHotelID=24963&HadPinnedHotel=true&regionId=6353650)

[See all 994 properties in Sheffield Island](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=04%2F10%2F2025&endDate=05%2F10%2F2025&regionId=6353650)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

### Discover the most popular places to visit in Sheffield Island

![Sheffield Island Lighthouse](https://mediaim.expedia.com/destination/2/0eda6d017413ea4d9213e753ce40e86d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Sheffield Island Lighthouse

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.

[](https://expedia.ca/Sheffield-Island-Lighthouse-Connecticut.d553248621558114961.Vacation-Attraction)

## Explore a world of travel with Expedia

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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## Go further with the Expedia app

Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app

![QR code to download the app](data:image/png;base64,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)