Title: Book the Best Shelter Island Heights WINERY Hotels in 2025 | Expedia.ca

  

[Hotels in Shelter Island Heights](https://expedia.ca/Shelter-Island-Heights-Hotels.d183716.Travel-Guide-Hotels)[Vacation Rentals in Shelter Island Heights](https://expedia.ca/Shelter-Island-Heights-Vacation-Rentals.d183716.Travel-Guide-VacationRentals)[Things to do in Shelter Island Heights](https://expedia.ca/Things-To-Do-In-Shelter-Island-Heights.d183716.Travel-Guide-Activities)[Shelter Island Heights Car Rentals](https://expedia.ca/Car-Rentals-In-Shelter-Island-Heights.d183716.Car-Rental-Guide)[Shelter Island Heights Vacation Packages](https://expedia.ca/Shelter-Island-Heights.d183716.Destination-Travel-Guides)

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# Find Winery Hotels in Shelter Island Heights, NY from CA $487

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## Check availability on Shelter Island Heights Winery Hotels

Tonight

[Sep 28 - Sep 29](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2025-09-28&endDate=2025-09-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Sep 29 - Sep 30](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2025-09-29&endDate=2025-09-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Shelter Island Heights Winery Hotels

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/fa5a1a49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/ad990fb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/988fd965.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/0122d57a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Pridwin Hotel

Shelter Island Heights

9.6/10

Exceptional

(78)

"Shelter Island is definitely a gem"

CA $388

CA $487 total

includes taxes & fees

Oct 19 - Oct 20

[](https://www.expedia.ca/Shelter-Island-Heights-Hotels-The-Pridwin-Hotel.h6473437.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/3000000/2360000/2355900/2355872/4cddecdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/3000000/2360000/2355900/2355872/0d3201a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/3000000/2360000/2355900/2355872/0a40cbb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room](https://images.trvl-media.com/lodging/3000000/2360000/2355900/2355872/f86d9acd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sunset Beach

Shelter Island Heights

9.0/10

Wonderful

(4)

"Great hotel on Shelter Island, pricey but nice. Rooms were really cute."

[](https://www.expedia.ca/Shelter-Island-Hotels-Sunset-Beach.h2355872.Hotel-Information)

![Kayaking](https://images.trvl-media.com/lodging/8000000/7750000/7749700/7749655/aaa24181.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dock](https://images.trvl-media.com/lodging/8000000/7750000/7749700/7749655/da5c172b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/8000000/7750000/7749700/7749655/4600fa3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/8000000/7750000/7749700/7749655/aa9ef8a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### SEVEN - Shelter Island Guest House

Shelter Island Heights

9.8/10

Exceptional

(57)

"It was a beautiful place! Under construction however, Beth was Amazing! Amelia was so hospitable. Close to everything and it certainly helped that the weather was spectacular! Will definitely go back another time!"

[](https://www.expedia.ca/Shelter-Island-Heights-Hotels-SEVEN-Shelter-Island-Guest-House.h7749655.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=2025-10-12&endDate=2025-10-13&regionId=183716&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true)

## Top Shelter Island Heights Hotel Reviews

![Water's Edge Resort & Spa](//images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg)

### Water's Edge Resort & Spa

10/10 Excellent

"clean and quiet property, great views, amazing staff"

[](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information)

![The Pridwin Hotel](//images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/fa5a1a49_y.jpg)

### The Pridwin Hotel

10/10 Excellent

"Shelter Island is definitely a gem"

[](https://expedia.ca/Shelter-Island-Heights-Hotels-The-Pridwin-Hotel.h6473437.Hotel-Information)

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-   [Hotels with Free Breakfast in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Hotels-With-Free-Breakfast.0-0-d157359-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels)
-   [Luxury Hotels in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Luxury-Hotel.0-0-d157359-tLuxuryHotel.Travel-Guide-Filter-Hotels)
-   [Oceanfront Hotels in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Oceanfront-Hotels.0-0-d157359-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
-   [Shopping Hotels in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Shopping-Hotel.0-0-d157359-tShoppingHotel.Travel-Guide-Filter-Hotels)
-   [Adults Only Resorts & in Silver Beach](https://www.expedia.ca/Silver-Beach-Shelter-Island-Hotels-Adults-Only-Resorts.0-n553248635976481903-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels)
-   [Cheap Hotels in Southold](https://www.expedia.ca/Southold-Hotels-Cheap-Hotels.0-0-d183719-tCheapHotels.Travel-Guide-Filter-Hotels)
-   [Romantic Hotels in Southold](https://www.expedia.ca/Southold-Hotels-Romantic-Hotel.0-0-d183719-tRomanticHotel.Travel-Guide-Filter-Hotels)
-   [Boutique Hotels in West Side](https://www.expedia.ca/West-Side-Hotels-Boutique-Hotel.0-0-d6203488-tBoutiqueHotel.Travel-Guide-Filter-Hotels)
-   [Cheap Hotels in West Side](https://www.expedia.ca/West-Side-Hotels-Cheap-Hotels.0-0-d6203488-tCheapHotels.Travel-Guide-Filter-Hotels)
-   [Family Hotels in West Side](https://www.expedia.ca/West-Side-Hotels-Family-Hotel.0-0-d6203488-tFamilyHotel.Travel-Guide-Filter-Hotels)
-   [Hotels with Free Breakfast in West Side](https://www.expedia.ca/West-Side-Hotels-Hotels-With-Free-Breakfast.0-0-d6203488-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels)
-   [Luxury Hotels in West Side](https://www.expedia.ca/West-Side-Hotels-Luxury-Hotel.0-0-d6203488-tLuxuryHotel.Travel-Guide-Filter-Hotels)
-   [Winery Hotels in West Side](https://www.expedia.ca/West-Side-Hotels-Winery-Hotel.0-0-d6203488-tWineryHotel.Travel-Guide-Filter-Hotels)

-   [Flights from Toronto (YYZ) to New York (NYC)](https://www.expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york)

-   [Book Winery Hotels in Shelter Island Heights on Expedia.com](https://www.expedia.com/Shelter-Island-Heights-Hotels-Winery-Hotel.0-0-d183716-tWineryHotel.Travel-Guide-Filter-Hotels)