Title: 4 Stars Hotels in Shelter Island, New York from CA $276 - Find Cheap Shelter Island Hotels With 4 Stars | 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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## Check availability on Shelter Island 4 Star Hotels

Tonight

[Mar 10 - Mar 11](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-03-10&endDate=2026-03-11&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Mar 11 - Mar 12](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-03-11&endDate=2026-03-12&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-03-13&endDate=2026-03-15&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-03-20&endDate=2026-03-22&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Shelter Island 4-star hotels

![Exterior](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/b29cbb53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Ocean View One Bedroom Suite](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/d3ce4464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/78273489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/0272b9dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gurney's Montauk Resort & Seawater Spa

[](https://www.expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information)

Montauk

8.4/10

Very good

(736 reviews)

"Room was spotless, staff were great and the resort is top notch!!"

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

Carrie

CA $502

CA $689 total

includes taxes & fees

Mar 15 - Mar 16

[](https://www.expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information)

![Resort view](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/7aeccb7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/8a4a605e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/ac1b5094.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lunch, dinner, brunch served; American cuisine, beach views ](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/55b708b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sound View Greenport

[](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information)

Greenport

8.4/10

Very good

(618 reviews)

"Nice place"

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

Mateusz

CA $208

CA $276 total

includes taxes & fees

Mar 26 - Mar 27

[](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/1ec18076.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/2000000/1210000/1209400/1209378/c4093211.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/72731801.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/edc3cd1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Madison Beach Hotel

[](https://www.expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.Hotel-Information)

Madison Center

9.4/10

Exceptional

(347 reviews)

"Staff and hotel are lovely "

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

Steven

CA $300

CA $345 total

includes taxes & fees

Mar 31 - Apr 1

[](https://www.expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.Hotel-Information)

![View from property](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/52063f27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/93f768d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/338f251a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/ecd1e47d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Journey East Hampton

[](https://www.expedia.ca/East-Hampton-Hotels-Journey-East-Hampton.h23252049.Hotel-Information)

East Hampton North

9.2/10

Wonderful

(164 reviews)

"Amazing stay"

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

Liana

CA $236

CA $297 total

includes taxes & fees

Mar 16 - Mar 17

[](https://www.expedia.ca/East-Hampton-Hotels-Journey-East-Hampton.h23252049.Hotel-Information)

![Property entrance](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/d7688cb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/3b892c7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Queen](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/6ddcc118.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)

### The Maidstone

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

East Hampton

8.0/10

Very good

(151 reviews)

"We had a wonderful stay "

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

Sabrina

CA $328

CA $375 total

includes taxes & fees

Apr 2 - Apr 3

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

![Outdoor pool](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/8b4b1f10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Library](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/88ff99e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/9423d3da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/db3d6717.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Topping Rose House

[](https://www.expedia.ca/Bridgehampton-Hotels-Topping-Rose-House.h5581380.Hotel-Information)

Bridgehampton

9.2/10

Wonderful

(143 reviews)

"Our second home :)"

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

olivia

CA $708

CA $813 total

includes taxes & fees

Mar 15 - Mar 16

[](https://www.expedia.ca/Bridgehampton-Hotels-Topping-Rose-House.h5581380.Hotel-Information)

![Beach bar](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/52eefc00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Waterfront Beach Shack Studio](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/fe6e5945.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Waterfront Beach Shack Studio](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/1c4953c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Waterfront Beach Shack Studio](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/244f3d92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Silver Sands Motel & Beach Bungalows

[](https://www.expedia.ca/Greenport-Hotels-Silver-Sands.h91068954.Hotel-Information)

Greenport

9.8/10

Exceptional

(147 reviews)

"Everything was excellent, best hotel on the north fork. "

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

Dan

[](https://www.expedia.ca/Greenport-Hotels-Silver-Sands.h91068954.Hotel-Information)

![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/f1ebef28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/69a951cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/22da4a39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/2fdf39bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hero Beach Club

[](https://www.expedia.ca/Montauk-Hotels-Hero-Beach-Club.h16544673.Hotel-Information)

Montauk

9.0/10

Wonderful

(203 reviews)

"Great weekend trip "

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

Timothy

CA $225

CA $396 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Montauk-Hotels-Hero-Beach-Club.h16544673.Hotel-Information)

![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/c585313b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/f58691c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/d3ed50cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/2cb5da15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Montauk Yacht Club

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

Montauk

8.6/10

Excellent

(1,000 reviews)

"Wonderful hotel and location "

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

FIONA

CA $319

CA $520 total

includes taxes & fees

Apr 2 - Apr 3

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

![2 restaurants, American cuisine](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/d3bf1318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/44f578e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/d269b9f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Carriage House | Living area](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/6a224301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The 1770 House Restaurant & Inn

[](https://www.expedia.ca/East-Hampton-Hotels-The-1770-House-Restaurant-Inn.h1085655.Hotel-Information)

East Hampton

9.8/10

Exceptional

(162 reviews)

"Wonderful Inn & staff…The restaurant is also excellent! "

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

Anthony

CA $360

CA $492 total

includes taxes & fees

Mar 11 - Mar 12

[](https://www.expedia.ca/East-Hampton-Hotels-The-1770-House-Restaurant-Inn.h1085655.Hotel-Information)

![Beach nearby, white sand, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/028711b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Frette Italian sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/06408853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/fa70e85b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/56f0c16b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Roundtree, Amagansett

[](https://www.expedia.ca/Amagansett-Hotels-The-Roundtree.h10547745.Hotel-Information)

Amagansett North

10/10

Exceptional

(93 reviews)

"Fantastic hotel, great location."

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

Tunca

CA $785

CA $942 total

includes taxes & fees

Mar 15 - Mar 16

[](https://www.expedia.ca/Amagansett-Hotels-The-Roundtree.h10547745.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/daf99b53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/f53e135a.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)

![Premium bedding, individually furnished, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/7a760b80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Pridwin Hotel

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

Shelter Island Heights

9.6/10

Exceptional

(84 reviews)

"Overall the places is nice, clean and great views"

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

Dianne

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

![Miss Anna James Room](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/w848h631x48y3-ad11e9c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Katharine Hepburn Room](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/20c673f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miss Anna James Room](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/dc6ad011.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/1891e70e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### James Pharmacy Bed & Breakfast

[](https://www.expedia.ca/Old-Saybrook-Hotels-James-Pharmacy-Bed-Breakfast.h78191036.Hotel-Information)

Old Saybrook Center

9.0/10

Wonderful

(23 reviews)

"Cute B&B, very nice room, check-in worked well"

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

Isolde

CA $410

CA $455 total

includes taxes & fees

Apr 7 - Apr 8

[](https://www.expedia.ca/Old-Saybrook-Hotels-James-Pharmacy-Bed-Breakfast.h78191036.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/a99c206a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Room, 1 Bedroom, Non Smoking (Room 314)](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/61b576aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/98c270a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast and dinner served](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/fb2335a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Copper Beech Inn

[](https://www.expedia.ca/Old-Saybrook-Hotels-Copper-Beech-Inn.h1484254.Hotel-Information)

Ivoryton

8.6/10

Excellent

(509 reviews)

"Very nice property. Very clean. Staff was very nice - very good breakfast. "

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

Marilyn

CA $379

CA $435 total

includes taxes & fees

Mar 11 - Mar 12

[](https://www.expedia.ca/Old-Saybrook-Hotels-Copper-Beech-Inn.h1484254.Hotel-Information)

![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/aa9cc8cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily cooked-to-order breakfast (USD 25 per person)](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/34ace0dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, free beach shuttle, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/650853cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bicycling](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/6893dda0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Canoe Place Inn and Cottages

[](https://www.expedia.ca/Hampton-Bays-Hotels-Canoe-Place-Inn-And-Cottages.h83519458.Hotel-Information)

Hampton Bays

9.8/10

Exceptional

(62 reviews)

"Wonderful stay! "

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

Lindsay

[](https://www.expedia.ca/Hampton-Bays-Hotels-Canoe-Place-Inn-And-Cottages.h83519458.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148848/b6601c88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148848/94958fa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Room, Multiple Beds, Harbour View](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148848/09f2080f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148848/75ed01fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Faraway Sag Harbor

[](https://www.expedia.ca/Sag-Harbor-Hotels-Barons-Cove.h1148848.Hotel-Information)

Sag Harbor

9.0/10

Wonderful

(292 reviews)

"Great location in the heart of town Walk to everything Amazing breakfast too "

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

Michael

[](https://www.expedia.ca/Sag-Harbor-Hotels-Barons-Cove.h1148848.Hotel-Information)

![One Bedroom Condo King with Ocean view | Living area](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/fd0f941b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room dining](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/0ca01820.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/804eaa5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![One Bedroom Condo King with Ocean view | Beach/ocean view](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/173765ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Offshore Residences

[](https://www.expedia.ca/Montauk-Hotels-Offshore-Residences.h118940366.Hotel-Information)

Downtown Montauk

10/10

Exceptional

(1 review)

CA $633

CA $878 total

includes taxes & fees

Mar 15 - Mar 16

[](https://www.expedia.ca/Montauk-Hotels-Offshore-Residences.h118940366.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/1190496c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/253d38d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/ef1a1d3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/5689ac07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Canoe Place Waterfront Residences

[](https://www.expedia.ca/Hampton-Bays-Hotels-Canoe-Place-Waterfront-Residences.h109662697.Hotel-Information)

Hampton Bays

10/10

Exceptional

(1 review)

[](https://www.expedia.ca/Hampton-Bays-Hotels-Canoe-Place-Waterfront-Residences.h109662697.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/90000000/89990000/89981800/89981758/7b5c5b88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/90000000/89990000/89981800/89981758/w1170h1164x0y1-82df79df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/90000000/89990000/89981800/89981758/602810ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89990000/89981800/89981758/w1169h650x0y0-3f68a3a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Rams Head Inn

[](https://www.expedia.ca/Shelter-Island-Heights-Hotels-The-Rams-Head-Inn.h89981758.Hotel-Information)

Shelter Island Heights

7.6/10

Good

(18 reviews)

"Beautiful views and lovely service "

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

Lana

[](https://www.expedia.ca/Shelter-Island-Heights-Hotels-The-Rams-Head-Inn.h89981758.Hotel-Information)

![Aerial view](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/4db6535f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/bbbb0bf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/6809b461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/d9c11af0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### East Hampton Art House Bed & Breakfast

[](https://www.expedia.ca/East-Hampton-Hotels-East-Hampton-Art-House-Bed-Breakfast.h31007589.Hotel-Information)

Clearwater Beach

9.6/10

Exceptional

(65 reviews)

"The hosts were really nice and the breakfast is excellent!"

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

IVAN

[](https://www.expedia.ca/East-Hampton-Hotels-East-Hampton-Art-House-Bed-Breakfast.h31007589.Hotel-Information)

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## Learn more about Shelter Island

Nestled between Long Island's forks, this serene island offers pristine beaches and kayaking through Mashomack Preserve's coastal wetlands. Rent bikes to explore historic mansions and stop at Sunset Beach for seafood with spectacular evening views across Shelter Bay.

[See all hotels in Shelter Island](https://www.expedia.ca/Hotel-Search?startDate=2026-03-24&endDate=2026-03-25&adults=2&regionId=157359)

![Central Park summer](https://images.trvl-media.com/place/157359/6c674470-f02c-495a-ad05-e592d3be267f.jpg?impolicy=fcrop&w=900&h=430&p=1&q=high)

## Top Shelter Island Hotel Reviews

![Gurney's Montauk Resort & Seawater Spa](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/b29cbb53_y.jpg)

### Gurney's Montauk Resort & Seawater Spa

8/10 Good

"I took my husband for a relaxing weekend for his birthday at Gurneys Resort. We had an ocean front room with a beautiful view! The room and resort was beautiful and clean. We hung out at GiGis bar a lot and the bar tenders were great! Super friendly and helpful! I loved our stay however I was truly disappointed to get a call on our check In day to tell us the indoor pool could not be used. That was literally what we wanted to do for the weekend was relax at the pool and eat and drink. I booked the trips weeks prior so to get a call the day of saying we can’t use to pool during our stay was truly disappointing. They waived the resort fee for the inconvenience, otherwise the weekend was great. "

[](https://expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information)

![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/7aeccb7c_y.jpg)

### Sound View Greenport

10/10 Excellent

"Staff was over the top helpful, nice!!!! If you needed help or anything they were right on it for you Thank you do very much for making a sad trip for a loved ones memorial into something grateful!!"

[](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information)

![Journey East Hampton](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/52063f27_y.jpg)

### Journey East Hampton

10/10 Excellent

"So cute and cozy! Extremely clean, check in staff was so sweet and attentive. 100% recommend for the price and value ! "

[](https://expedia.ca/East-Hampton-Hotels-Journey-East-Hampton.h23252049.Hotel-Information)

## Find out more about Shelter Island

If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Shelter Island are calling your name. Known for providing first-rate service in amazing locations, each of the Shelter Island 4 Stars hotels lets discerning travelers bask in an unforgettable experience.

Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day.

It’s all waiting for you at the top four star hotels in Shelter Island. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Shelter Island, New York, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Shelter Island hotels with 4 Stars provide everything you need to unwind in style.

## Frequently asked questions

### What are the best 4-star hotels in Shelter Island?

### How much does it cost to stay in a 4-star hotel in Shelter Island?

> - Search for the lowest price from CA $276

### What's the difference between 5-star and 4-star hotels in Shelter Island?

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

- [Visit East Marion ](https://www.expedia.ca/East-Marion.dx6069914)
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