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

 

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Photo by Brian V. Rowe

# Find Ski Hotels in Shelter Island Heights, NY

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## Check availability on Shelter Island Heights Ski Hotels

Tonight

[Nov 22 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2025-11-22&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Nov 23 - Nov 24](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2025-11-23&endDate=2025-11-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Shelter Island Heights Ski Hotels

No exact matches found, but these alternatives could be just right

## Recommended hotels in Shelter Island Heights

![View from property](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/51be5ca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/d7311f73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/ae8f0ca6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lake](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/8cc5044d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### House on Chase Creek

The Heights

9.4/10

Exceptional

(79)

" This was my husband and my first time visiting Shelter Island and I feel lucky that my stay was at the House of ChaseCreek. Bill was excellent in helping us navigate our stay on the Island which made for an enjoyable experience. The house was charming , very clean , and had easy access to the town restaurant s, and Ferry. Highly recommend ! "

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

Maureen

CA $261

CA $298 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Shelter-Island-Heights-Hotels-House-On-Chase-Creek.h12610909.Hotel-Information)

![Ocean View 2 Queens](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/6944012d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/6f247566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Ocean View 2 Queens with Kitchenette | Private kitchen](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/294d9a91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/c614d2a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Offshore Montauk

Montauk

9.4/10

Exceptional

(69)

"Excellent stay! Gorgeous views, very clean rooms, helpful staff and beautifully done. Will stay again!"

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

Erica

CA $115

CA $211 total

includes taxes & fees

Dec 10 - Dec 11

[](https://www.expedia.ca/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/10000000/9520000/9517100/9517042/w3834h2560x6y0-25f93ce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 King Bed, Non Smoking, Refrigerator & Microwave (Shower Only)](https://images.trvl-media.com/lodging/10000000/9520000/9517100/9517042/a2ae6476.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily self-serve breakfast for a fee](https://images.trvl-media.com/lodging/10000000/9520000/9517100/9517042/c2934dcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, laptop workspace, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/10000000/9520000/9517100/9517042/708b4a67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Best Western Niantic - New London/Mystic Area

Niantic

9.0/10

Wonderful

(437)

"Very nice property and staff was great!"

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

George

CA $130

CA $150 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Niantic-Hotels-Best-Western-Niantic-Inn.h9517042.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/afdef753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/72f65e39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a48f4b96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

8.0/10

Very good

(1000)

"Always a great stay at Pier Blue. Comfy bed and plenty of room."

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

Patricia

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

![Front of property - evening/night](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/96463a2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/8f0a0367.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 2 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/37cdbc57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/d18d0d4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Montauk Manor

Montauk

9.2/10

Wonderful

(1262)

"Always excellent, even suring my eleventh stay."

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

Daryl

CA $195

CA $251 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information)

![One Bedroom Harbor View Terrace Suite | View from room](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/4e8534b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Balcony view](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/64ea9871.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/a8d80546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Harbor Front Inn

Greenport

8.8/10

Excellent

(535)

"Amazing property, rooms, and staff. Book a room with a balcony for amazing views!"

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

Matthew

CA $147

CA $237 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information)

![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/724b2312.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage, 2 Bedrooms, Patio](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/58473cf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/6b9fb589.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage, 1 Bedroom, Patio](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/e582d722.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### North Fork Cottages & RV Resort

Greenport

9.4/10

Exceptional

(6)

"great place to stay, clean and quiet....loved it"

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

Darlin

CA $247

CA $283 total

includes taxes & fees

Nov 25 - Nov 26

[](https://www.expedia.ca/Greenport-Hotels-North-Fork-Cottages-RV-Resort.h121214797.Hotel-Information)

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/4e86636a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/35541bfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/efe89d02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/78e3666a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kenny's Tipperary Inn

Culloden Shores

8.4/10

Very good

(877)

"Very clean and spacious room! "

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

Mary Beth

[](https://www.expedia.ca/Montauk-Hotels-Kennys-Tipperary-Inn.h8474914.Hotel-Information)

![Indoor pool, a heated pool](https://images.trvl-media.com/lodging/1000000/860000/851700/851700/cf19af3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/860000/851700/851700/81065c8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/860000/851700/851700/c8355f59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 King Bed with Sofa bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/860000/851700/851700/a58a238d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sleep Inn & Suites Niantic North

Niantic

8.4/10

Very good

(1011)

"The room was clean and perfect for a nights stay"

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

joshua

CA $110

CA $127 total

includes taxes & fees

Dec 9 - Dec 10

[](https://www.expedia.ca/Niantic-Hotels-Sleep-Inn-Suites-Niantic.h851700.Hotel-Information)

![On the beach](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/691fdd98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/909788b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, coffee/tea maker, cookware/dishes/utensils, spices](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/b6de66d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/5b4c06e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Stern at Soundview · Beach+Ocean+Sunrise

Old Lyme

10/10

Exceptional

(3)

"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "

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

Lylian

CA $107

CA $273 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Old-Lyme-Hotels-The-Stern-At-Soundview-BeachOceanViewSunrise.h106147914.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=2025-12-06&endDate=2025-12-07&regionId=183716&adults=2&location_highlights_explore=ski&sort=RECOMMENDED&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

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[Book now](https://expedia.ca/deals?rfrr=AFFINITY_BF_PROMO_183716)

## Top Shelter Island Heights Hotel Reviews

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-   [Golf Hotels in Fishers Island](https://www.expedia.ca/Fishers-Island-Hotels-Golf-Hotel.0-0-d1208-tGolfHotel.Travel-Guide-Filter-Hotels)
-   [Luxury Hotels in Fishers Island](https://www.expedia.ca/Fishers-Island-Hotels-Luxury-Hotel.0-0-d1208-tLuxuryHotel.Travel-Guide-Filter-Hotels)
-   [Spa Hotels in Fishers Island](https://www.expedia.ca/Fishers-Island-Hotels-Spa-Hotel.0-0-d1208-tSpaHotel.Travel-Guide-Filter-Hotels)
-   [Adults Only Resorts & in Greenport](https://www.expedia.ca/Greenport-Hotels-Adults-Only-Resorts.0-0-d110728-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels)
-   [Beach Hotel Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Beach-Hotel.0-0-d110728-tBeachHotel.Travel-Guide-Filter-Hotels)
-   [Boutique Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Boutique-Hotel.0-0-d110728-tBoutiqueHotel.Travel-Guide-Filter-Hotels)
-   [Cheap Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Cheap-Hotels.0-0-d110728-tCheapHotels.Travel-Guide-Filter-Hotels)
-   [Hotels & Resorts for Couples in Greenport](https://www.expedia.ca/Greenport-Hotels-Couples-Resorts-Hotels.0-0-d110728-tCouplesResortsHotels.Travel-Guide-Filter-Hotels)
-   [Lake Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Lake-Hotels.0-0-d110728-tLakeHotels.Travel-Guide-Filter-Hotels)
-   [Luxury Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Luxury-Hotel.0-0-d110728-tLuxuryHotel.Travel-Guide-Filter-Hotels)
-   [Oceanfront Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Oceanfront-Hotels.0-0-d110728-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
-   [Shopping Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Shopping-Hotel.0-0-d110728-tShoppingHotel.Travel-Guide-Filter-Hotels)
-   [Spa Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Spa-Hotel.0-0-d110728-tSpaHotel.Travel-Guide-Filter-Hotels)
-   [Waterpark Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Waterpark-Hotels.0-0-d110728-tWaterparkHotels.Travel-Guide-Filter-Hotels)
-   [Beach Hotel Hotels in Greenport West](https://www.expedia.ca/Greenport-West-Hotels-Beach-Hotel.0-0-d553248635975876381-tBeachHotel.Travel-Guide-Filter-Hotels)
-   [Cheap Hotels in Greenport West](https://www.expedia.ca/Greenport-West-Hotels-Cheap-Hotels.0-0-d553248635975876381-tCheapHotels.Travel-Guide-Filter-Hotels)
-   [Adults Only Resorts & in Hay Beach](https://www.expedia.ca/Hay-Beach-Shelter-Island-Hotels-Adults-Only-Resorts.0-n553248635976470037-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels)
-   [Casino Hotels in Hay Beach](https://www.expedia.ca/Hay-Beach-Shelter-Island-Hotels-Casino-Hotel.0-n553248635976470037-0-tCasinoHotel.Travel-Guide-Filter-Hotels)
-   [All Inclusive Resorts and in Long Island](https://www.expedia.ca/Long-Island-Hotels-All-Inclusive-Hotel.0-0-d602887-tAllInclusiveHotel.Travel-Guide-Filter-Hotels)
-   [Green Hotels in Long Island](https://www.expedia.ca/Long-Island-Hotels-Green-Sustainable.0-0-d602887-tGreenSustainable.Travel-Guide-Filter-Hotels)
-   [Hotels with Balconies in Long Island](https://www.expedia.ca/Long-Island-Hotels-Hotels-With-Balconies.0-0-d602887-tHotelswithBalconies.Travel-Guide-Filter-Hotels)
-   [Hotels with Free Breakfast in Long Island](https://www.expedia.ca/Long-Island-Hotels-Hotels-With-Free-Breakfast.0-0-d602887-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels)
-   [Lgbt Friendly Hotels in Long Island](https://www.expedia.ca/Long-Island-Hotels-LGBT-Friendly-Hotel.0-0-d602887-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels)
-   [Beach Hotel Hotels in Manhattan](https://www.expedia.ca/Manhattan-New-York-Hotels-Beach-Hotel.0-n129440-0-tBeachHotel.Travel-Guide-Filter-Hotels)
-   [Hotels & Resorts for Couples in Manhattan](https://www.expedia.ca/Manhattan-New-York-Hotels-Couples-Resorts-Hotels.0-n129440-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels)
-   [Golf Hotels in Manhattan](https://www.expedia.ca/Manhattan-New-York-Hotels-Golf-Hotel.0-n129440-0-tGolfHotel.Travel-Guide-Filter-Hotels)
-   [Green Hotels in Manhattan](https://www.expedia.ca/Manhattan-New-York-Hotels-Green-Sustainable.0-n129440-0-tGreenSustainable.Travel-Guide-Filter-Hotels)
-   [Honeymoon Resorts and in Manhattan](https://www.expedia.ca/Manhattan-New-York-Hotels-Honeymoon-Hotels.0-n129440-0-tHoneymoonHotels.Travel-Guide-Filter-Hotels)
-   [Hotels with Wifi in Manhattan](https://www.expedia.ca/Manhattan-New-York-Hotels-Hotel-With-Wifi.0-n129440-0-tHotelwithwifi.Travel-Guide-Filter-Hotels)
-   [Hotels with a Lazy River in Manhattan](https://www.expedia.ca/Manhattan-New-York-Hotels-Hotels-With-A-Lazy-River.0-n129440-0-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels)
-   [Hotels with Childcare in Manhattan](https://www.expedia.ca/Manhattan-New-York-Hotels-Hotels-With-Childcare.0-n129440-0-tHotelswithChildcare.Travel-Guide-Filter-Hotels)
-   [Lgbt Friendly Hotels in Manhattan](https://www.expedia.ca/Manhattan-New-York-Hotels-LGBT-Friendly-Hotel.0-n129440-0-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels)
-   [Mountain Hotels in Manhattan](https://www.expedia.ca/Manhattan-New-York-Hotels-Mountain-Hotels.0-n129440-0-tMountainHotels.Travel-Guide-Filter-Hotels)
-   [Oceanfront Hotels in Manhattan](https://www.expedia.ca/Manhattan-New-York-Hotels-Oceanfront-Hotels.0-n129440-0-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
-   [Winery Hotels in Manhattan](https://www.expedia.ca/Manhattan-New-York-Hotels-Winery-Hotel.0-n129440-0-tWineryHotel.Travel-Guide-Filter-Hotels)
-   [Adults Only Resorts & in Midtown East](https://www.expedia.ca/Midtown-East-New-York-Hotels-Adults-Only-Resorts.0-n6141525-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels)
-   [New York Hotels](https://www.expedia.ca/New-York-Hotels.d178293.Travel-Guide-Hotels)
-   [Casino Hotels in Purchase](https://www.expedia.ca/Purchase-Hotels-Casino-Hotel.0-0-d6172129-tCasinoHotel.Travel-Guide-Filter-Hotels)
-   [Hotels with Free Airport Shuttle in Purchase](https://www.expedia.ca/Purchase-Hotels-Hotels-With-Free-Airport-Shuttle.0-0-d6172129-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels)
-   [Spa Hotels in Purchase](https://www.expedia.ca/Purchase-Hotels-Spa-Hotel.0-0-d6172129-tSpaHotel.Travel-Guide-Filter-Hotels)
-   [Adults Only Resorts & in Queens](https://www.expedia.ca/Queens-New-York-Hotels-Adults-Only-Resorts.0-n149004-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels)
-   [Shopping Hotels in Queens](https://www.expedia.ca/Queens-New-York-Hotels-Shopping-Hotel.0-n149004-0-tShoppingHotel.Travel-Guide-Filter-Hotels)
-   [Adults Only Resorts & in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Adults-Only-Resorts.0-0-d157359-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels)
-   [Beach Hotel Hotels in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Beach-Hotel.0-0-d157359-tBeachHotel.Travel-Guide-Filter-Hotels)
-   [Boutique Hotels in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Boutique-Hotel.0-0-d157359-tBoutiqueHotel.Travel-Guide-Filter-Hotels)
-   [Cheap Hotels in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Cheap-Hotels.0-0-d157359-tCheapHotels.Travel-Guide-Filter-Hotels)
-   [Hotels & Resorts for Couples in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Couples-Resorts-Hotels.0-0-d157359-tCouplesResortsHotels.Travel-Guide-Filter-Hotels)
-   [Family Hotels in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Family-Hotel.0-0-d157359-tFamilyHotel.Travel-Guide-Filter-Hotels)
-   [Hotels with a Pool in Shelter Island](https://www.expedia.ca/Shelter-Island-Hotels-Hotel-With-Pool.0-0-d157359-tHotelwithPool.Travel-Guide-Filter-Hotels)
-   [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 Ski Hotels in Shelter Island Heights on Expedia.com](https://www.expedia.com/Shelter-Island-Heights-Hotels-Ski-Hotel.0-0-d183716-tSkiHotel.Travel-Guide-Filter-Hotels)