Title: Sheffield Island Villas  | 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

![](https://images.trvl-media.com/place/9245/c630a679-4303-4d4f-b558-8074390c35c3.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=6353650&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=6353650&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=6353650&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=6353650&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Sheffield Island villas

![Luxury Villa, Garden View | Dining](https://images.trvl-media.com/lodging/123000000/122970000/122960900/122960872/7d17eab9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Villa, Garden View | Living area](https://images.trvl-media.com/lodging/123000000/122970000/122960900/122960872/f4457c92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Villa, Garden View | Interior](https://images.trvl-media.com/lodging/123000000/122970000/122960900/122960872/5f200c64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Villa, Garden View | Living area](https://images.trvl-media.com/lodging/123000000/122970000/122960900/122960872/f9d5743a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury NYC Home with Free Parking for 12

[](https://www.expedia.ca/White-Plains-Hotels-Luxury-NYC-Home-With-Free-Parking-For-12.h122960872.Hotel-Information)

White Plains

CA $598

CA $910 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/White-Plains-Hotels-Luxury-NYC-Home-With-Free-Parking-For-12.h122960872.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/124000000/123350000/123346400/123346355/dde34060_edited_b0ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123350000/123346400/123346355/66f12c5f_edited_45be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/123350000/123346400/123346355/279d1dca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/124000000/123350000/123346400/123346355/3ffc94b7_edited_7c06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury NYC Home Game Room Free Parking

[](https://www.expedia.ca/White-Plains-Hotels-Luxury-NYC-Home-Game-Room-Free-Parking.h123346355.Hotel-Information)

White Plains

CA $729

CA $1,037 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/White-Plains-Hotels-Luxury-NYC-Home-Game-Room-Free-Parking.h123346355.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-18&endDate=2026-02-19&regionId=6353650&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Sheffield+Island%2C+Connecticut%2C+United+States+of+America&regionId=6353650&latLong=41.050985%2C-73.416767&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Sheffield+Island%2C+Connecticut%2C+United+States+of+America&regionId=6353650&latLong=41.050985%2C-73.416767&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=APARTMENT)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Sheffield+Island%2C+Connecticut%2C+United+States+of+America&regionId=6353650&latLong=41.050985%2C-73.416767&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=VILLA)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Sheffield+Island%2C+Connecticut%2C+United+States+of+America&regionId=6353650&latLong=41.050985%2C-73.416767&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=CONDO)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Sheffield+Island%2C+Connecticut%2C+United+States+of+America&regionId=6353650&latLong=41.050985%2C-73.416767&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=COTTAGE)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Sheffield+Island%2C+Connecticut%2C+United+States+of+America&regionId=6353650&latLong=41.050985%2C-73.416767&adults=2&startDate=2026-05-05&d1=2026-05-05&endDate=2026-05-08&d2=2026-05-08&lodging=VACATION_HOME)

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## Top Sheffield Island Hotel Reviews

![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

"Very clean, beautifully decorated and comfortable night's sleep. Staff was very polite and helpful. Breakfast was much better quality than most offered at other hotels, great selection."

[](https://expedia.ca/Woodbury-Hotels-The-Inn-At-Fox-Hollow-Hotel.h871849.Hotel-Information)

![The Watershed](https://images.trvl-media.com/lodging/7000000/6030000/6020100/6020007/c1a1bbc5_y.jpg)

### The Watershed

10/10 Excellent

"Beautiful hotel. Rooms are spacious and updated. The staff are absolutely wonderful. I highly recommend. The bed was comfy and the bathroom was updated and spotless. "

[](https://expedia.ca/Stamford-Hotels-Hotel-Zero-Degrees-Norwalk.h6020007.Hotel-Information)

![Amsterdam Hotel](https://images.trvl-media.com/lodging/1000000/30000/20800/20793/f5bb9592_y.jpg)

### Amsterdam Hotel

10/10 Excellent

"Room was very clean upon arrival. Staff was very friendly. "

[](https://expedia.ca/Stamford-Hotels-Amsterdam-Hotel.h20793.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

"clean, usb-c socket, very friendly staff, free shuttle to airport..,"

[](https://expedia.ca/White-Plains-Hotels-Sonesta-White-Plains-Downtown.h9979.Hotel-Information)

![SureStay Plus by Best Western Woodbury Inn](https://images.trvl-media.com/lodging/1000000/60000/57000/56928/88325d15_y.jpg)

### SureStay Plus by Best Western Woodbury Inn

10/10 Excellent

"The staff is nice & very accommodating, rooms are clean, always enjoy staying here."

[](https://expedia.ca/Woodbury-Hotels-Best-Western-Woodbury-Inn.h56928.Hotel-Information)

![Norwalk Inn & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/15200/15114/13ab5174_y.jpg)

### Norwalk Inn & Conference Center

10/10 Excellent

"Everything was great! Very nice hotel! Would stay there again,"

[](https://expedia.ca/Stamford-Hotels-Norwalk-Inn.h15114.Hotel-Information)

![Trumbull Marriott Shelton](https://images.trvl-media.com/lodging/1000000/10000/1200/1166/b3c487eb_y.jpg)

### Trumbull Marriott Shelton

10/10 Excellent

"Wonderful "

[](https://expedia.ca/New-Haven-Hotels-Trumbull-Marriott-Shelton.h1166.Hotel-Information)

![Hyatt Regency Greenwich](https://images.trvl-media.com/lodging/1000000/20000/18200/18180/19d28016_y.jpg)

### Hyatt Regency Greenwich

10/10 Excellent

"Reception was amazing and the room was impeccable. The Hyatt in Greenwhich has been maintaining the stunning atrium for years and it adds so much that can’t be said to everyone’s stay. "

[](https://expedia.ca/Stamford-Hotels-Hyatt-Regency-Greenwich.h18180.Hotel-Information)

![Marriott Melville Long Island](https://images.trvl-media.com/lodging/1000000/20000/15800/15742/76d16bae_y.jpg)

### Marriott Melville Long Island

10/10 Excellent

"Everything was very clean. Staff very welcoming. Enjoyed our stay."

[](https://expedia.ca/Melville-Hotels-Marriott-Melville-Long-Island.h15742.Hotel-Information)

## Find out more about Sheffield Island

## Sheffield Island Villas information

| Number of reviews |        |
| ----------------- | ------ |
| Accommodation     | Villas |
| Lowest Price      |        |
| Highest Price     |        |

## Frequently asked questions

### Why book your villa in Sheffield Island with Expedia?

### How can I find cheap villas in Sheffield Island?

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- [Lodges in Stamford ](https://www.expedia.ca/Stamford-Lodges.d602523-aaLodges.Travel-Guide-Accommodation)
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- [Residences in Stamford ](https://www.expedia.ca/Stamford-Residences.d602523-aaResidences.Travel-Guide-Accommodation)
- [Hotels near Stamford Town Center ](https://www.expedia.ca/Stamford-Town-Center-Hotels.0-l6125753-0.Travel-Guide-Filter-Hotels)
- [Hotels near The Maritime Aquarium ](https://www.expedia.ca/The-Maritime-Aquarium-Hotels.0-l553248621555566147-0.Travel-Guide-Filter-Hotels)
- [Hotels near The SoNo Collection ](https://www.expedia.ca/The-SoNo-Collection-Hotels.0-l759370593496035328-0.Travel-Guide-Filter-Hotels)
- [Vacation Homes in Westport Station ](https://www.expedia.ca/Westport-Station-Private-Vacation-Homes.d553248635977407805-aaPrivateVacationHomes.Travel-Guide-Accommodation)

- [Flights to Darien ](https://www.expedia.ca/Cheap-Flights-To-Darien.d7557.Travel-Guide-Flights)
- [Flights to Norwalk ](https://www.expedia.ca/Cheap-Flights-To-Norwalk.d9245.Travel-Guide-Flights)
- [Flights to Rowayton ](https://www.expedia.ca/Cheap-Flights-To-Rowayton.d3000430454.Travel-Guide-Flights)
- [Flights from Norwalk Islands ](https://www.expedia.ca/lp/flights/6347888/flights-from-norwalk-islands)
- [Flights from Darien ](https://www.expedia.ca/lp/flights/7557/flights-from-darien)
- [Flights from Norwalk ](https://www.expedia.ca/lp/flights/9245/flights-from-norwalk)

- [Compo Beach ](https://www.expedia.ca/Compo-Beach-Westport.d553248621532664563.Vacation-Attraction)
- [Norwalk Islands Vacations ](https://www.expedia.ca/Norwalk-Islands.d6347888.Destination-Travel-Guides)
- [Visit Norwalk Islands ](https://www.expedia.ca/Norwalk-Islands.dx6347888)
- [Sheffield Island Lighthouse ](https://www.expedia.ca/Sheffield-Island-Lighthouse-Connecticut.d553248621558114961.Vacation-Attraction)

- [Alamo Rent A Car Rental Cars in Norwalk Islands ](https://www.expedia.ca/Alamo-Rent-A-Car-Car-Rentals-In-Norwalk-Islands.d6347888-c6.Car-Rental-Guide-Suppliers)
- [Avis Rental Cars in Norwalk ](https://www.expedia.ca/Avis-Car-Rentals-In-Norwalk.d9245-c41.Car-Rental-Guide-Suppliers)
- [Car rental Darien ](https://www.expedia.ca/Car-Rentals-In-Darien.d7557.Car-Rental-Guide)
- [Car rental Norwalk ](https://www.expedia.ca/Car-Rentals-In-Norwalk.d9245.Car-Rental-Guide)
- [Hertz Rental Cars in Norwalk Islands ](https://www.expedia.ca/Hertz-Car-Rentals-In-Norwalk-Islands.d6347888-c40.Car-Rental-Guide-Suppliers)
- [Payless Rental Cars in Norwalk Islands ](https://www.expedia.ca/Payless-Car-Rentals-In-Norwalk-Islands.d6347888-c38.Car-Rental-Guide-Suppliers)
- [Rent A Wreck Rental Cars in Norwalk ](https://www.expedia.ca/Rent-A-Wreck-Car-Rentals-In-Norwalk.d9245-c33.Car-Rental-Guide-Suppliers)

- [Norwalk Islands Vacation Rentals ](https://www.expedia.ca/Norwalk-Islands-Vacation-Rentals.d6347888.Travel-Guide-VacationRentals)
- [Norwalk Vacation Rentals ](https://www.expedia.ca/Norwalk-Vacation-Rentals.d9245.Travel-Guide-VacationRentals)
- [Sherwood Island State Park Vacation Rentals ](https://www.expedia.ca/Sherwood-Island-State-Park-Vacation-Rentals.d6248407.Travel-Guide-VacationRentals)

- [Things to do in Stamford ](https://www.expedia.ca/Things-To-Do-In-Stamford.d602523.Travel-Guide-Activities)

- [Book Villas in Sheffield Island on Expedia.com ](https://www.expedia.com/Sheffield-Island-Villas.d6353650-aaVillas.Travel-Guide-Accommodation)