Title: 5 Stars Hotels in Sheffield Island, Connecticut from CA $168 - 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) ![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 # 5 Stars Hotels in Sheffield Island, Connecticut from CA $168 - ![](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 5 Star Hotels Tonight [Jan 2 - Jan 3](https://www.expedia.ca/Hotel-Search?regionId=6353650&startDate=2026-01-02&endDate=2026-01-03&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 3 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6353650&startDate=2026-01-03&endDate=2026-01-04&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6353650&startDate=2026-01-02&endDate=2026-01-04&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6353650&startDate=2026-01-09&endDate=2026-01-11&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Sheffield Island 5-star hotels ![Exterior](https://images.trvl-media.com/lodging/2000000/1790000/1789400/1789323/80a97b29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1790000/1789400/1789323/45a95d2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite, 1 Bedroom](https://images.trvl-media.com/lodging/2000000/1790000/1789400/1789323/w4000h2662x0y0-aae7375c.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/daf1d0e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Opus Westchester, Autograph Collection [](https://www.expedia.ca/White-Plains-Hotels-The-Opus-Westchester.h1789323.Hotel-Information) White Plains 9.2/10 Wonderful (529) "our room was very clean on beds very comfortable staff friendly, breakfast wonderful" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan CA $438 CA $548 total includes taxes & fees Jan 8 - Jan 9 [](https://www.expedia.ca/White-Plains-Hotels-The-Opus-Westchester.h1789323.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/120000000/119250000/119248500/119248411/6e17e1d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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](https://images.trvl-media.com/lodging/120000000/119250000/119248500/119248411/564422c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119250000/119248500/119248411/9a855962.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beechmont - Perfect for Family Retreat! [](https://www.expedia.ca/Bridgeport-Hotels-Beechmont.h119248411.Hotel-Information) North End CA $1,161 CA $1,815 total includes taxes & fees Jan 5 - Jan 6 [](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. ![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 $217 CA $294 total Feb 1 - Feb 2 includes taxes & fees 8.6/10 Excellent! (1,168 reviews) [](https://expedia.ca/White-Plains-Hotels-Sonesta-White-Plains-Downtown.h9979.Hotel-Information) ![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 $146 CA $168 total Jan 4 - Jan 5 includes taxes & fees 8.6/10 Excellent! (1,408 reviews) [](https://expedia.ca/Stamford-Hotels-Norwalk-Inn.h15114.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 $255 CA $293 total Jan 23 - Jan 24 includes taxes & fees 8.4/10 Very Good! (1,005 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=03%2F01%2F2026&endDate=04%2F01%2F2026®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=03%2F01%2F2026&endDate=04%2F01%2F2026®ionId=6353650&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F01%2F2026&endDate=04%2F01%2F2026®ionId=6353650&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F01%2F2026&endDate=04%2F01%2F2026®ionId=6353650&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F01%2F2026&endDate=04%2F01%2F2026®ionId=6353650&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F01%2F2026&endDate=04%2F01%2F2026®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=2026-01-16&endDate=2026-01-17&adults=2®ionId=6353650) ![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=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? > - Search for the lowest price per night from CA $168 ### What makes a hotel 5 stars in Sheffield Island? ### Are there any 5-star all-inclusive resorts in Sheffield Island? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [3 Star Hotels in New Canaan ](https://www.expedia.ca/3Star-New-Canaan-Hotels.s30-0-d137514.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Northford ](https://www.expedia.ca/3Star-Northford-Hotels.s30-0-d6004524.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Beacon Falls ](https://www.expedia.ca/4Star-Beacon-Falls-Hotels.s40-0-d6348182.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Bridgeport ](https://www.expedia.ca/4Star-Bridgeport-Hotels.s40-0-d525.Travel-Guide-Filter-Hotels) - 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