Title: Book the Best Shelter Island Heights LUXURY Hotels - Upscale Hotels in Shelter Island Heights, NY | Expedia.ca

  

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## Check availability on Shelter Island Heights Luxury Hotels

Tonight

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

Tomorrow

[Sep 30 - Oct 1](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2025-09-30&endDate=2025-10-01&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

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

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## Top Shelter Island Heights Luxury Hotels

![Kayaking](https://images.trvl-media.com/lodging/8000000/7750000/7749700/7749655/aaa24181.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)

![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/8000000/7750000/7749700/7749655/40ff476f.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=2025-10-13&endDate=2025-10-14&regionId=183716&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true)

## Top Shelter Island Heights Hotel Reviews

![Saybrook Point Resort & Marina](//images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108_y.jpg)

### Saybrook Point Resort & Marina

10/10 Excellent

"Loved everything about this property. Location, Staff, Amenities. Decor and furniture beautiful. "

[](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information)

![Quality Inn Old Saybrook - Westbrook](//images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg)

### Quality Inn Old Saybrook - Westbrook

10/10 Excellent

"Clean, quiet, friendly staff."

[](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information)

![Pier Blue Inn Old Saybrook - Essex](//images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg)

### Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"Highly recommend!"

[](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information)

![Montauk Yacht Club](//images.trvl-media.com/lodging/1000000/10000/7000/6970/fcfc464f_y.jpg)

### Montauk Yacht Club

10/10 Excellent

"Wonderful hotel and location "

[](https://expedia.ca/Montauk-Hotels-Gurneys-Star-Island-Resort-Marina.h6970.Hotel-Information)

## Frequently asked questions

### Are you looking for a luxury hotel for your stay in Shelter Island Heights?

> Use Expedia to arrange your flight to East Hampton, NY (HTO) airport or Fishers Island, NY (FID-Elizabeth Field) airport, and then select from a variety of places to stay that will deliver the luxury you want. Amenities are important when you plan a trip, so we make it easy to find what you need to make your stay relaxing and comfortable. If you want an upscale hotel with a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Shelter Island Heights has to offer. Shelter Island Heights has some interesting things to see and do including Sunset Beach and Crescent Beach, so you might want to take in the local sights during your visit.

### When can I expect good weather in Shelter Island Heights?

> Planning for the weather is an important factor for making your trip to Shelter Island Heights a success, especially when you're splurging. The hottest months are usually August and July with an average temp of 70°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Shelter Island Heights is 57 inches.

### What's there to see and do in Shelter Island Heights?

> Enjoy Shelter Island Heights with a stop at Sunset Beach, Crescent Beach, and Shelter Island Country Club. If you have a little extra time during your trip, you might want to check out Sylvester Manor and Menhadden Lane Beach.

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