Title: Book the Best Sheffield Island LUXURY Hotels - Upscale Hotels in Sheffield Island, CT | 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)[Sheffield Island Vacation Packages](https://expedia.ca/Sheffield-Island.d6353650.Destination-Travel-Guides) ![A nice spot for a picnic and a stroll along the beach. ](https://images.trvl-media.com/place/9245/c630a679-4303-4d4f-b558-8074390c35c3.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Richard Miska # Find luxury hotels in Sheffield Island, CT - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Sheffield Island Luxury Hotels Tonight [Dec 8 - Dec 9](https://www.expedia.ca/Hotel-Search?regionId=6353650&startDate=2025-12-08&endDate=2025-12-09&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Dec 9 - Dec 10](https://www.expedia.ca/Hotel-Search?regionId=6353650&startDate=2025-12-09&endDate=2025-12-10&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=6353650&startDate=2025-12-12&endDate=2025-12-14&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6353650&startDate=2025-12-19&endDate=2025-12-21&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Top Sheffield Island Luxury Hotels ## Top Sheffield Island Hotel Reviews ![Days Inn by Wyndham Woodbury Long Island](https://images.trvl-media.com/lodging/1000000/10000/6700/6675/2e6a9e91_y.jpg) ### Days Inn by Wyndham Woodbury Long Island 10/10 Excellent "Clean and comfy " [](https://expedia.ca/Woodbury-Hotels-Days-Inn-By-Wyndham-Woodbury-Long-Island.h6675.Hotel-Information) ![The Circle Hotel Fairfield](https://images.trvl-media.com/lodging/10000000/9820000/9816500/9816438/b1e811bb_y.jpg) ### The Circle Hotel Fairfield 10/10 Excellent "Clean, updated room, easy check in & out. Staff was very nice" [](https://expedia.ca/New-Haven-Hotels-The-Circle-Hotel-Fairfield.h9816438.Hotel-Information) ![The Inn At Fox Hollow Hotel](https://images.trvl-media.com/lodging/1000000/880000/871900/871849/9f9215cb_y.jpg) ### The Inn At Fox Hollow Hotel 10/10 Excellent "Yes. Yes." [](https://expedia.ca/Woodbury-Hotels-The-Inn-At-Fox-Hollow-Hotel.h871849.Hotel-Information) ![East Norwich Inn](https://images.trvl-media.com/lodging/1000000/10000/2100/2024/fa5b4526_y.jpg) ### East Norwich Inn 10/10 Excellent "Very friendly staff, great room. A comfortable bed, a clean shower, and a working TV. I enjoyed my stay and I will be back. " [](https://expedia.ca/East-Norwich-Hotels-East-Norwich-Inn-Oyster-Bay.h2024.Hotel-Information) ![HYATT house White Plains](https://images.trvl-media.com/lodging/1000000/430000/427300/427283/458cd7c2_y.jpg) ### HYATT house White Plains 10/10 Excellent "Yes all was good" [](https://expedia.ca/White-Plains-Hotels-HYATT-House-White-Plains.h427283.Hotel-Information) ![The Stamford Hotel](https://images.trvl-media.com/lodging/1000000/50000/42300/42258/d312d428_y.jpg) ### The Stamford Hotel 10/10 Excellent "Loved the amount of space and how clean it was ❤️" [](https://expedia.ca/Stamford-Hotels-The-Stamford-Hotel.h42258.Hotel-Information) ![Red Carpet Inn](https://images.trvl-media.com/lodging/3000000/2930000/2928100/2928037/49d204da_y.jpg) ### Red Carpet Inn 10/10 Excellent "Todo vien" [](https://expedia.ca/Stamford-Hotels-Red-Carpet-Inn.h2928037.Hotel-Information) ![Sonesta White Plains Downtown](https://images.trvl-media.com/lodging/1000000/10000/10000/9979/2c718cc1_y.jpg) ### Sonesta White Plains Downtown 10/10 Excellent "Great stay" [](https://expedia.ca/White-Plains-Hotels-Sonesta-White-Plains-Downtown.h9979.Hotel-Information) ![Hyatt Regency Greenwich](https://images.trvl-media.com/lodging/1000000/20000/18200/18180/19d28016_y.jpg) ### Hyatt Regency Greenwich 10/10 Excellent "Excellent service " [](https://expedia.ca/Stamford-Hotels-Hyatt-Regency-Greenwich.h18180.Hotel-Information) ## Frequently asked questions ### Are you searching for a great accommodation for your luxury getaway to Sheffield Island? ### When can I expect good weather in Sheffield Island? ### What's there to see and do in Sheffield Island? ## Explore a world of travel with Expedia - 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