Title: 5 Stars Hotels in Sheffield Island, Connecticut from CA $179 - Find Cheap Sheffield Island Hotels With 5 Stars | 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)[Flights to Sheffield Island](https://expedia.ca/Cheap-Flights-To-Sheffield-Island.d6353650.Travel-Guide-Flights)[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) ![](https://mediaim.expedia.com/destination/2/0eda6d017413ea4d9213e753ce40e86d.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Richard Miska # 5 Stars Hotels in Sheffield Island, Connecticut from CA $179 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 5 Star Hotels Tonight [Sep 18 - Sep 19](https://www.expedia.ca/Hotel-Search?regionId=6353650&startDate=2025-09-18&endDate=2025-09-19&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 19 - Sep 20](https://www.expedia.ca/Hotel-Search?regionId=6353650&startDate=2025-09-19&endDate=2025-09-20&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 19 - Sep 21](https://www.expedia.ca/Hotel-Search?regionId=6353650&startDate=2025-09-19&endDate=2025-09-21&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=6353650&startDate=2025-09-26&endDate=2025-09-28&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Sheffield Island 5 Star Hotels ## Our top choices for Sheffield Island 5-star hotels ![Exterior](https://images.trvl-media.com/lodging/2000000/1790000/1789400/1789323/3a855b0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sauna, steam room, body treatments, hydrotherapy, hot stone massages](https://images.trvl-media.com/lodging/2000000/1790000/1789400/1789323/711b91ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite, 1 Bedroom, Non Smoking | Living area](https://images.trvl-media.com/lodging/2000000/1790000/1789400/1789323/w4000h2662x0y0-ce6de22a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1790000/1789400/1789323/d48ded99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Opus Westchester, Autograph Collection White Plains 9.2/10 Wonderful (509) "Beautiful hotel. Great location. " CA $440 CA $551 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/White-Plains-Hotels-The-Opus-Westchester.h1789323.Hotel-Information) ![Premium House, Garden View | Living area](https://images.trvl-media.com/lodging/120000000/119250000/119248500/119248411/78c118d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium House, Garden View | Terrace/patio](https://images.trvl-media.com/lodging/120000000/119250000/119248500/119248411/35645e22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium House, Garden View | Terrace/patio](https://images.trvl-media.com/lodging/120000000/119250000/119248500/119248411/63283601.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/120000000/119250000/119248500/119248411/564422c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beechmont - Perfect for Family Retreat! Bridgeport CA $839 CA $1,448 total includes taxes & fees Sep 21 - Sep 22 [](https://www.expedia.ca/Bridgeport-Hotels-Beechmont.h119248411.Hotel-Information) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Sheffield-Island-Hotels.s50-0-d6353650.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Sheffield-Island-Hotels.s50-0-d6353650.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Sheffield Island. ![Norwalk Inn & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/15200/15114/13ab5174_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Norwalk Inn & Conference Center 99 East Avenue, Norwalk, CT CA $155 CA $179 total Sep 21 - Sep 22 includes taxes & fees 8.6/10 Excellent! (1,304 reviews) [](https://expedia.ca/Stamford-Hotels-Norwalk-Inn.h15114.Hotel-Information) ![Sonesta White Plains Downtown](https://images.trvl-media.com/lodging/1000000/10000/10000/9979/2c718cc1_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Sonesta White Plains Downtown 66 Hale Ave, White Plains, NY CA $245 CA $320 total Oct 12 - Oct 13 includes taxes & fees 8.6/10 Excellent! (1,105 reviews) [](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?impolicy=resizecrop&rw=402&ra=fit) ### Hyatt Regency Greenwich 1800 E Putnam Avenue, Old Greenwich, CT CA $280 CA $322 total Oct 2 - Oct 3 includes taxes & fees 8.2/10 Very Good! (1,006 reviews) [](https://expedia.ca/Stamford-Hotels-Hyatt-Regency-Greenwich.h18180.Hotel-Information) Still don't see what you're looking for? [See all properties in Sheffield Island.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=20%2F09%2F2025&endDate=21%2F09%2F2025®ionId=6353650&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=20%2F09%2F2025&endDate=21%2F09%2F2025®ionId=6353650&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=20%2F09%2F2025&endDate=21%2F09%2F2025®ionId=6353650&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=20%2F09%2F2025&endDate=21%2F09%2F2025®ionId=6353650&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=20%2F09%2F2025&endDate=21%2F09%2F2025®ionId=6353650&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=20%2F09%2F2025&endDate=21%2F09%2F2025®ionId=6353650&star=50&star=50&amenities=WATER_PARK) 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. ## Learn more about Sheffield Island Experience Sheffield Island: its island views, monuments, and more! [See all hotels in Sheffield Island](https://www.expedia.ca/Hotel-Search?startDate=2025-10-03&endDate=2025-10-04&adults=2®ionId=6353650) ![](https://mediaim.expedia.com/destination/2/0eda6d017413ea4d9213e753ce40e86d.jpg?impolicy=fcrop&w=899&h=600&p=1&q=high) Photo by Richard Miska ## Top Sheffield Island Hotel Reviews ## Find out more about Sheffield Island ## Five Star Hotels in Sheffield Island There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Sheffield Island so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Sheffield Island and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Sheffield Island Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places. Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town. #### Make Your Escape to Sheffield Island The results are in, and Sheffield Island 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Sheffield Island! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Sheffield Island today and settle down in the lap of luxury tomorrow. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Sheffield Island? > You'll find several pricing options for a 5-star hotel in Sheffield Island on Expedia. How much you'll pay will depend on your travel dates, trip length and other factors. Compare available properties for your desired dates and use our pricing and other filters to find the perfect high-end stay. > > > > - Search for the lowest price per night from CA $179 ### What makes a hotel 5 stars in Sheffield Island? > In Sheffield Island, a hotel must offer a specific level of upscale conveniences to earn a 5-star rating. These may include gourmet restaurants, on-site gyms, saunas and spas, premium bedding, luxury toiletries and more. What also sets 5-star hotels apart is their exceptional standard of service. You'll enjoy things like in-room massages, concierge services and nightly turn-down services. Some may also offer additional touches like a welcome gift. ### Are there any 5-star all-inclusive resorts in Sheffield Island? > Use our filter tool to find an upscale escape in Sheffield Island where most of what you need is included in the price. After your initial search, narrow down your results for resorts that have a 5-star rating and are categorized as "All inclusive." The main thing on the schedule at these stays? 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[Things to do in Stamford](https://www.expedia.ca/Things-To-Do-In-Stamford.d602523.Travel-Guide-Activities) - [Book 5 Star Hotels in Sheffield Island on Expedia.com](https://www.expedia.com/5Star-Sheffield-Island-Hotels.s50-0-d6353650.Travel-Guide-Filter-Hotels)