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

  

[Shelter Island Travel Guide](https://expedia.ca/Shelter-Island.dx157359)[Hotels in Shelter Island](https://expedia.ca/Shelter-Island-Hotels.d157359.Travel-Guide-Hotels)[Vacation Rentals in Shelter Island](https://expedia.ca/Shelter-Island-Vacation-Rentals.d157359.Travel-Guide-VacationRentals)[Flights to Shelter Island](https://expedia.ca/Cheap-Flights-To-Shelter-Island.d157359.Travel-Guide-Flights)[Things to do in Shelter Island](https://expedia.ca/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities)[Shelter Island Car Rentals](https://expedia.ca/Car-Rentals-In-Shelter-Island.d157359.Car-Rental-Guide)[Shelter Island Vacation Packages](https://expedia.ca/Shelter-Island.d157359.Destination-Travel-Guides)

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# Find Boutique Hotels in Shelter Island, NY

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## Check availability on Shelter Island Boutique Hotels

Tonight

[Oct 28 - Oct 29](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-28&endDate=2025-10-29&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-29&endDate=2025-10-30&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-31&endDate=2025-11-02&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-11-07&endDate=2025-11-09&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Shelter Island Boutique Hotels

![Exterior](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden Suite, Wheelchair Accessible, Ground Floor, 2 Queen Beds, Non-Smoking](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/20957ef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/dc9e5678.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/bfb5cc4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Zey Hotel

Greenport

9.2/10

Wonderful

(282)

"Such a cute little hotel. Stayed one night bc we had a wedding in the area. Everything was great - the staff was exceptional."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Phyllis

CA $368

CA $421 total

includes taxes & fees

Oct 29 - Oct 30

[](https://www.expedia.ca/Greenport-Hotels-The-Gallery-Hotel.h15622089.Hotel-Information)

![Front of property - evening/night](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/99260f7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/32700dd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/968c61db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Georgia Pond Junior Suite](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/386602b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Maidstone

East Hampton

8.0/10

Very good

(150)

"We had a wonderful stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sabrina

CA $760

CA $869 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/East-Hampton-Hotels-The-Maidstone.h9652095.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=2025-11-11&endDate=2025-11-12&regionId=157359&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true)

## Top Shelter Island Hotel Reviews

## Frequently asked questions

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

> Once you've decided where you'd like to stay in scenic Shelter Island, consider what to do for fun during your trip. Experience the cultural highlights around Shelter Island with a visit to Railroad Museum of Long Island, LongHouse Reserve, and Guild Hall. You might also like to explore more of the area and take in additional sights like Sunset Beach, Crescent Beach, and Parrish Art Museum while you're here.

### What kind of weather should I plan for when I travel to Shelter Island?

> Understanding the weather in Shelter Island will help you enjoy your stay to the fullest. 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 is 57 inches.

### What's the best way to get to my boutique hotel in Shelter Island?

> You have a few options for getting to Shelter Island. The nearest major airport is East Hampton, NY (HTO), which is located 8.8 mi (14.2 km) from the heart of the city, but Fishers Island, NY (FID-Elizabeth Field) may also be an option. If you'd like to venture out around the area, you may want a rental car for your journey.

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-   [Spa Hotels in Shelter Island Heights](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Spa-Hotel.0-0-d183716-tSpaHotel.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 Boutique Hotels in Shelter Island on Expedia.com](https://www.expedia.com/Shelter-Island-Hotels-Boutique-Hotel.0-0-d157359-tBoutiqueHotel.Travel-Guide-Filter-Hotels)