Title: Book the Best BOUTIQUE Hotels in Shelter Island in 2026 | 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)

![Central Park summer](https://images.trvl-media.com/place/157359/6c674470-f02c-495a-ad05-e592d3be267f.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Find Boutique Hotels in Shelter Island, NY from CA $381

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## Check availability on Shelter Island Boutique Hotels

Tonight

[Dec 27 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-12-27&endDate=2025-12-28&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 28 - Dec 29](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-12-28&endDate=2025-12-29&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-01-02&endDate=2026-01-04&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-01-09&endDate=2026-01-11&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for 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)

![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)

![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)

![Restaurant](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/942c49f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Zey Hotel

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

Greenport

9.2/10

Wonderful

(290)

"Loved this place. Lots of places to relax and play games. Super-friendly staff. Can't wait to go back b"

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

Susie

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

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

![Lobby sitting area](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/a9768080.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)

![Front of property - evening/night](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/5021abf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Maidstone

[](https://www.expedia.ca/East-Hampton-Hotels-The-Maidstone.h9652095.Hotel-Information)

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 $333

CA $381 total

includes taxes & fees

Dec 30 - Dec 31

[](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=2026-01-11&endDate=2026-01-12&regionId=157359&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true)

## Top Shelter Island Hotel Reviews

![Hyatt Place Long Island East End](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/9bf973cb_y.jpg)

### Hyatt Place Long Island East End

10/10 Excellent

"Our room had a great view of the river and marina. we also loved the seating area in the room. Very comfortable"

[](https://expedia.ca/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.Hotel-Information)

## Frequently asked questions

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

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

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

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