Title: 4 Stars Hotels in Shelter Island, New York from CA $381 - Find Cheap Shelter Island Hotels With 4 Stars | Expedia.ca

  

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# 4 Stars Hotels in Shelter Island, New York from CA $381

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## Check availability on Shelter Island 4 Star Hotels

Tonight

[Oct 18 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-18&endDate=2025-10-19&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 19 - Oct 20](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-19&endDate=2025-10-20&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-31&endDate=2025-11-02&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Shelter Island 4 Star Hotels

![Outdoor wedding area](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/895004c9.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)

![Children's activities](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/5a7a4c79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Oceanfront Two Bedroom Suite | Living area](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/60539ea4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gurney's Montauk Resort & Seawater Spa

Montauk

8.2/10

Very good

(671)

"Amazing resort, very friendly staff, food and drinks are Amazing! We enjoyed our stay. "

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

Amandip

CA $378

CA $517 total

includes taxes & fees

Nov 4 - Nov 5

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

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/4c9856c1.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/16000000/15280000/15273200/15273178/43997189.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 2 Queen Beds](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/f76cf168.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sound View Greenport

Greenport

8.4/10

Very good

(579)

"Loved everything about my stay at the Sound view !! "

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

Sabrina

CA $313

CA $426 total

includes taxes & fees

Oct 26 - Oct 27

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

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/619dc6c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/00b9aef3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/b1a067ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Courtyard Double Queen](https://images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/07fb7947.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Marram

Montauk

8.8/10

Excellent

(235)

"It was an amazing relaxing weekend. We want to come back next year the same weekend!"

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

Piera

CA $278

CA $446 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Montauk-Hotels-Marram.h15408228.Hotel-Information)

![Indoor pool, 2 outdoor pools](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/fcfc464f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach, beach towels, kayaking, fishing](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/d705542f.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)

![Marina](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/c7873724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Montauk Yacht Club

Montauk

8.6/10

Excellent

(1004)

"Wonderful hotel and location "

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

FIONA

CA $261

CA $458 total

includes taxes & fees

Nov 2 - Nov 3

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

![Exterior](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/18df186b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/625fce42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 2 Bedrooms](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/b8f87b0c.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/2000000/1210000/1209400/1209378/1ef9d54f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Madison Beach Hotel

Madison Center

9.4/10

Exceptional

(323)

"the staff was exceptional and our dinner was very good"

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

john

CA $344

CA $395 total

includes taxes & fees

Oct 30 - Oct 31

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

![View from room](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/77f9f5ea.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)

![Sports facility](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/abb4b75e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/72bc8ec9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hero Beach Club

Montauk

9.0/10

Wonderful

(196)

"Beach view and cozy vibes"

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

Christopher

CA $214

CA $381 total

includes taxes & fees

Oct 26 - Oct 27

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

![Exterior](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/acd2c1de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, in-room safe, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/7c3abc76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/a84ab4fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/d697dbfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Journey East Hampton

East Hampton North

9.0/10

Wonderful

(153)

"We were able to access many beaches with the beach pass that came with the stay. That was the main reason we wanted to stay there. The rooms were very nice, spacious and comfortable. "

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

Sarah

CA $360

CA $452 total

includes taxes & fees

Oct 19 - Oct 20

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

![Standard Cottage](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/5c9db42d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Signature Cottage | Private kitchen](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/4648b1d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Executive Cottage](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/6d8b086b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Canoe Place Inn and Cottages

Hampton Bays

9.8/10

Exceptional

(58)

"Amazing property. Really enjoyed our stay."

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

Dave

CA $575

CA $697 total

includes taxes & fees

Oct 20 - Oct 21

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

![Restaurant](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148848/w2881h1827x0y0-498cd175.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Suite, 1 King Bed with Sofa bed, Balcony, Bay View (Harbor Loft Suite - Water View)](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148848/21a500ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Designer toiletries, hair dryer, bathrobes, towels](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148848/6d1902d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Village King Room](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148848/df08158f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Faraway Sag Harbor

Sag Harbor

9.0/10

Wonderful

(291)

"staff seemed tired and fed up of people staying!"

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

andrew

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

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/fa5a1a49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/988fd965.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/75893d43.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)

### The Pridwin Hotel

Shelter Island Heights

9.6/10

Exceptional

(82)

"Clean room excellent staff"

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

Concetta

CA $478

CA $601 total

includes taxes & fees

Oct 19 - Oct 20

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

![Exterior](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/780134b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Waterfront Beach Shack Studio](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/65a8ebbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, down comforters, pillowtop beds, minibar](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/c930d525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Silver Sands Motel & Beach Bungalows

Greenport

9.8/10

Exceptional

(136)

"Great hotel and location. "

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

Lyn

CA $362

CA $414 total

includes taxes & fees

Oct 22 - Oct 23

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

![Beach nearby, white sand, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/b8adcc4e.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/c6fa26de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/1f4433ce.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)

### The Roundtree, Amagansett

Amagansett North

9.8/10

Exceptional

(88)

"The Roundtree was one of the most peaceful hotels we’ve ever stayed in. I highly recommend for a romantic getaway. "

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

Sabrina

CA $974

CA $1,169 total

includes taxes & fees

Nov 2 - Nov 3

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

![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)

![Staircase](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/475ef317.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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 211)](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/89c2227e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Copper Beech Inn

Ivoryton

8.6/10

Excellent

(504)

"Had a fantastic room 324 in the newer building.. Breakfast was delicious and service terrific.."

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

Anita

CA $391

CA $450 total

includes taxes & fees

Oct 20 - Oct 21

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

![Exterior](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/e9d81899.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/d84c46bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage, 2 Single Beds | View from room](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/9125969a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Topping Rose House

Bridgehampton

9.2/10

Wonderful

(135)

"Great rooms, staff and food"

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

Alexandra

CA $751

CA $863 total

includes taxes & fees

Oct 19 - Oct 20

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

![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/e9e14566.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 $737

CA $843 total

includes taxes & fees

Oct 19 - Oct 20

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

![Point of interest](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/e61ec435.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)

![Point of interest](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/f09f38b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### James Pharmacy Bed & Breakfast

Old Saybrook Center

9.2/10

Wonderful

(19)

"My husband and I stayed here for a quick weekend getaway and loved our experience! The location was perfect - located near restaurants, shops, and the beach - and the room was clean and charming. We will definitely be back!"

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

Rachel

CA $424

CA $470 total

includes taxes & fees

Oct 19 - Oct 20

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

![Garden](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/67db121e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room 4, King Bed](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/bf954008.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)

![Garden](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/3e8af6f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The 1770 House Restaurant & Inn

East Hampton

9.8/10

Exceptional

(157)

"The staff was incredibly genuine and the property felt intimate and comfortable."

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

Aniya

CA $442

CA $604 total

includes taxes & fees

Oct 26 - Oct 27

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

![One Bedroom Condo King with Steam Shower | Living area](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/fa3ad3aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![One Bedroom Condo King with Steam Shower | Terrace/patio](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/8db6a5b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![One Bedroom Condo King with Steam Shower](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/80b0c655.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![One Bedroom Condo King with Steam Shower | Living area](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/a9bb02b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Offshore Residences

Downtown Montauk

CA $742

CA $1,008 total

includes taxes & fees

Oct 19 - Oct 20

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

![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)

![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)

![Private kitchen](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/574b952f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, 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)

### Canoe Place Waterfront Residences

Hampton Bays

10/10

Exceptional

(1)

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/54000000/53900000/53890800/53890717/754e4cf1_edited_1afd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/54000000/53900000/53890800/53890717/c4934e10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/54000000/53900000/53890800/53890717/b51e6bb8_edited_d588.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/54000000/53900000/53890800/53890717/248f6e18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pool/5 min walk to Beach/Restaurants/Museums- Village House w/backyard

Sag Harbor

10/10

Exceptional

(11)

"We spent an awesome week at Ray’s house. The pictures were completely accurate and it was so easy to communicate with Ray (and his helpful assistant). Super comfortable beds and great linens. We were traveling with 3 young kids and he went above and beyond - put up a fence around the pool, had a travel crib, high chair and some silicone plates/cups. The location was great. An easy walk to town and the bay beach. Makes a huge difference during high season with all the traffic. Would definitely...

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

Jessica T.

[](https://www.expedia.ca/Sag-Harbor-Hotels-5-Min-Walk-To-Beach-Restaurants-Museums-Village-House-With-Large-Backyard.h53890717.Hotel-Information)

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Save an average of 15% on thousands of hotels when you're signed in

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## Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Shelter Island.

![Mill House Inn](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/e0e0def6_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Mill House Inn

31 North Main Street, East Hampton, NY

CA $456

CA $573 total

Oct 27 - Oct 28

includes taxes & fees

9/10 Wonderful! (70 reviews)

[](https://expedia.ca/East-Hampton-Hotels-Mill-House-Inn.h2861838.Hotel-Information)

![Casa Newmark Holiday home 7 BestStayz.1](https://images.trvl-media.com/lodging/33000000/32420000/32411100/32411044/23f4590c_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Casa Newmark Holiday home 7 BestStayz.1

112 Northwest Path, Sagaponack, NY

[Get rates](https://expedia.ca/Hotel-Search?startDate=01%2F11%2F2025&endDate=02%2F11%2F2025&selected=32411044&PinnedHotelID=32411044&HadPinnedHotel=true&regionId=157359)

[](https://expedia.ca/Sagaponack-Hotels-Casa-Newmark-Holiday-Home-7-BestStayz1.h32411044.Hotel-Information)

Still don't see what you're looking for?

[See all properties in Shelter Island.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=19%2F10%2F2025&endDate=20%2F10%2F2025&regionId=157359&star=40)

You can also use these popular filters to refine your search.

[Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=19%2F10%2F2025&endDate=20%2F10%2F2025&regionId=157359&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=19%2F10%2F2025&endDate=20%2F10%2F2025&regionId=157359&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=19%2F10%2F2025&endDate=20%2F10%2F2025&regionId=157359&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=19%2F10%2F2025&endDate=20%2F10%2F2025&regionId=157359&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=19%2F10%2F2025&endDate=20%2F10%2F2025&regionId=157359&star=40&star=40&amenities=WATER_PARK)

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.

## 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=2025-11-01&endDate=2025-11-02&adults=2&regionId=157359)

![](https://mediaim.expedia.com/destination/2/57db4dbbb841fe5852df8ed4b2f64ec5.jpg?impolicy=fcrop&w=400&h=400&p=1&q=high)

Photo by tom owens

## Top Shelter Island Hotel Reviews

![Marram](//images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/619dc6c0_y.jpg)

### Marram

10/10 Excellent

"Ocean ciew"

[](https://expedia.ca/Montauk-Hotels-Marram.h15408228.Hotel-Information)

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

### Montauk Yacht Club

10/10 Excellent

"Staffs were so kind. The place was peaceful and it is really a relaxing place to stay especially it is beach front"

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

![Sound View Greenport](//images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg)

### Sound View Greenport

10/10 Excellent

"Nice views on sunset"

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

![Gurney's Montauk Resort & Seawater Spa](//images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/895004c9_y.jpg)

### Gurney's Montauk Resort & Seawater Spa

10/10 Excellent

"wonderful place only criticism is how far away rooms are from lobby and the rest of the facilities"

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

> [The Pridwin Hotel](https://www.expedia.ca/Shelter-Island-Heights-Hotels-The-Pridwin-Hotel.h6473437.Hotel-Information) is a 4-star hotel in Shelter Island that ranks highly among Expedia customers. A terrace and concierge services are some of its many amenities. Travellers also love staying at [Silver Sands Motel & Beach Bungalows](https://www.expedia.ca/Greenport-Hotels-Silver-Sands.h91068954.Hotel-Information). From a terrace to dining romance packages, it features conveniences that cater to all aspects of your relaxation and entertainment.

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

> Expedia can help you quickly track down the ideal 4-star hotel for your vacation in Shelter Island. Use our handy filter tool to tailor your search by things like price, amenities and star rating and get access to terrific deals in a few clicks.
> 
>   
> 
> -   Search for the lowest price from CA $573

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

> Treat yourself to refined living during your Shelter Island escape by staying at a 4-star hotel. As well as featuring upmarket accommodations, these retreats are typically packed with amenities such as complimentary bathrobes, large beds and more. A 5-star hotel will go the extra mile to make your trip an even more indulgent and unforgettable one. Round-the-clock concierge assistance, elegant furnishings and gourmet dining are a few of the superior conveniences and services you'll likely get access to.

## Explore a world of travel with Expedia

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-   [Shelter Island Heights Hotels](https://www.expedia.ca/Shelter-Island-Heights-Hotels.d183716.Travel-Guide-Hotels)
-   [Resorts in Shelter Island Heights](https://www.expedia.ca/Shelter-Island-Heights-Resort-Hotels.d183716-aaResortHotels.Travel-Guide-Accommodation)
-   [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)
-   [Silver Beach Hotels](https://www.expedia.ca/Silver-Beach-Shelter-Island-Hotels.0-n553248635976481903-0.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)
-   [Southold Hotels](https://www.expedia.ca/Southold-Hotels.d183719.Travel-Guide-Hotels)
-   [Motels in Southold](https://www.expedia.ca/Southold-Motels.d183719-aaMotels.Travel-Guide-Accommodation)
-   [Hotels near Sunset Beach](https://www.expedia.ca/Sunset-Beach-Hotels.0-l553248626388141313-0.Travel-Guide-Filter-Hotels)
-   [The Heights Hotels](https://www.expedia.ca/The-Heights-Shelter-Island-Heights-Hotels.0-n553248635976473534-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Wades Beach](https://www.expedia.ca/Wades-Beach-Hotels.0-l553248621554204759-0.Travel-Guide-Filter-Hotels)

-   [Flights to Greenport](https://www.expedia.ca/Cheap-Flights-To-Greenport.d110728.Travel-Guide-Flights)
-   [Flights from Southold](https://www.expedia.ca/lp/flights/183719/flights-from-southold)
-   [Flights from North Haven](https://www.expedia.ca/lp/flights/553248634998589872/flights-from-north-haven)
-   [Flights from East Marion](https://www.expedia.ca/lp/flights/6069914/flights-from-east-marion)
-   [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)
-   [Visit Pipes Cove](https://www.expedia.ca/Greenport-Pipes-Cove.dx553248635976473295)
-   [Kontokosta Winery](https://www.expedia.ca/Kontokosta-Winery-Greenport.d6326928.Vacation-Attraction)
-   [Visit North Haven](https://www.expedia.ca/North-Haven.dx553248634998589872)
-   [Visit Bay Point](https://www.expedia.ca/Sag-Harbor-Bay-Point.dx553248635976471151)
-   [Shelter Island Heights Vacations](https://www.expedia.ca/Shelter-Island-Heights.d183716.Destination-Travel-Guides)

-   [Car rental Greenport](https://www.expedia.ca/Car-Rentals-In-Greenport.d110728.Car-Rental-Guide)

-   [Things to do in Greenport](https://www.expedia.ca/Things-To-Do-In-Greenport.d110728.Travel-Guide-Activities)
-   [Things to do in Shelter Island Heights](https://www.expedia.ca/Things-To-Do-In-Shelter-Island-Heights.d183716.Travel-Guide-Activities)

-   [Book 4 Star Hotels in Shelter Island on Expedia.com](https://www.expedia.com/4Star-Shelter-Island-Hotels.s40-0-d157359.Travel-Guide-Filter-Hotels)