Title: 4 Stars Hotels in Shelter Island Heights, New York from CA $382 - Find Cheap Shelter Island Heights Hotels With 4 Stars | Expedia.ca

  

[Shelter Island Heights Travel Guide](https://expedia.ca/Shelter-Island-Heights.dx183716)[Hotels in Shelter Island Heights](https://expedia.ca/Shelter-Island-Heights-Hotels.d183716.Travel-Guide-Hotels)[Vacation Rentals in Shelter Island Heights](https://expedia.ca/Shelter-Island-Heights-Vacation-Rentals.d183716.Travel-Guide-VacationRentals)[Flights to Shelter Island Heights](https://expedia.ca/Cheap-Flights-To-Shelter-Island-Heights.d183716.Travel-Guide-Flights)[Things to do in Shelter Island Heights](https://expedia.ca/Things-To-Do-In-Shelter-Island-Heights.d183716.Travel-Guide-Activities)[Shelter Island Heights Car Rentals](https://expedia.ca/Car-Rentals-In-Shelter-Island-Heights.d183716.Car-Rental-Guide)[Shelter Island Heights Vacation Packages](https://expedia.ca/Shelter-Island-Heights.d183716.Destination-Travel-Guides)

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Photo by Erisa Dilo

# 4 Stars Hotels in Shelter Island Heights, New York from CA $382

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## Check availability on Shelter Island Heights 4 Star Hotels

Tonight

[Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2025-10-17&endDate=2025-10-18&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 18 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2025-10-18&endDate=2025-10-19&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=183716&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Shelter Island Heights 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)

![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)

![Oceanfront One Bedroom Suite | Terrace/patio](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/3a4c2dc9.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)

### 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. "

![](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)

![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)

![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)

![Meeting facility](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/4c9856c1.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 !! "

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

Sabrina

CA $314

CA $427 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)

![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)

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

![Bicycling](https://images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/6da50c27.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!"

![](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)

![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)

![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/5c314659.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)

### Montauk Yacht Club

Montauk

8.6/10

Excellent

(1004)

"Wonderful hotel and location "

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

FIONA

CA $262

CA $459 total

includes taxes & fees

Oct 30 - Oct 31

[](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)

![Lunch, dinner, brunch served; American cuisine, beach views ](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/a4958436.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)

![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)

### Madison Beach Hotel

Madison Center

9.4/10

Exceptional

(323)

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

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

john

CA $344

CA $396 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)

![Hero King Patio Deluxe | Terrace/patio](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/65048075.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)

![Sports facility](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/abb4b75e.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"

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

Christopher

CA $215

CA $382 total

includes taxes & fees

Oct 23 - Oct 24

[](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)

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/c353f8fd.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)

![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)

### Journey East Hampton

East Hampton North

9.0/10

Wonderful

(152)

"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. "

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

Sarah

CA $360

CA $452 total

includes taxes & fees

Nov 9 - Nov 10

[](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)

![Signature Suite](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/9bf97ebb.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)

![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."

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

Dave

CA $583

CA $707 total

includes taxes & fees

Oct 19 - Oct 20

[](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!"

![](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)

![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)

![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)

### The Pridwin Hotel

Shelter Island Heights

9.6/10

Exceptional

(82)

"Clean room excellent staff"

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

Concetta

CA $479

CA $602 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. "

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

Lyn

CA $363

CA $415 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/11000000/10550000/10547800/10547745/06408853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bicycling](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/65a49724.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)

### 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. "

![](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)

![Luxury Room, 1 Bedroom, Non Smoking (Room 322)](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/94ca860b.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)

### Copper Beech Inn

Ivoryton

8.6/10

Excellent

(504)

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

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

Anita

CA $392

CA $451 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)

![Premium bedding, minibar, in-room safe, desk](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/3f4839f2.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)

### Topping Rose House

Bridgehampton

9.2/10

Wonderful

(135)

"Great rooms, staff and food"

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

Alexandra

CA $1,118

CA $1,283 total

includes taxes & fees

Oct 31 - Nov 1

[](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/10000000/9660000/9652100/9652095/386602b3.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)

### The Maidstone

East Hampton

8.0/10

Very good

(150)

"We had a wonderful stay "

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

Sabrina

CA $730

CA $835 total

includes taxes & fees

Oct 26 - Oct 27

[](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)

![Garden](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/98031383.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/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!"

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

Rachel

CA $424

CA $471 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)

![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)

![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)

### The 1770 House Restaurant & Inn

East Hampton

9.8/10

Exceptional

(157)

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

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

Aniya

CA $443

CA $605 total

includes taxes & fees

Oct 30 - Oct 31

[](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)

![Exterior](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/439e74da.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)

### Offshore Residences

Downtown Montauk

CA $743

CA $1,010 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/110000000/109670000/109662700/109662697/934c8d81.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)

![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)

### 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)

![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)

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

![Smart TV, fireplace, table tennis, stereo](https://images.trvl-media.com/lodging/54000000/53900000/53890800/53890717/w3455h2297x0y1-853cf7f5.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...

![](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 Heights.

![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=31%2F10%2F2025&endDate=01%2F11%2F2025&selected=32411044&PinnedHotelID=32411044&HadPinnedHotel=true&regionId=183716)

[](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 Heights.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F10%2F2025&endDate=19%2F10%2F2025&regionId=183716&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=18%2F10%2F2025&endDate=19%2F10%2F2025&regionId=183716&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F10%2F2025&endDate=19%2F10%2F2025&regionId=183716&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F10%2F2025&endDate=19%2F10%2F2025&regionId=183716&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F10%2F2025&endDate=19%2F10%2F2025&regionId=183716&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F10%2F2025&endDate=19%2F10%2F2025&regionId=183716&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 Heights

Victorian homes line the streets of this charming hamlet where you can rent bikes to explore the island's quiet beaches. Reserve a table at one of the waterfront restaurants for sunset views or take the short ferry to Greenport for more dining options.

[See all hotels in Shelter Island Heights](https://www.expedia.ca/Hotel-Search?startDate=2025-10-31&endDate=2025-11-01&adults=2&regionId=183716)

![](https://mediaim.expedia.com/destination/2/4941e2fd68ce17b39e6de73e44df4c4b.jpg?impolicy=fcrop&w=900&h=492&p=1&q=high)

Photo by Erisa Dilo

## Top Shelter Island Heights Hotel Reviews

![The Pridwin Hotel](//images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/fa5a1a49_y.jpg)

### The Pridwin Hotel

10/10 Excellent

"Nice property"

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

![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)

![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 Heights

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 Heights are calling your name. Known for providing first-rate service in amazing locations, each of the Shelter Island Heights 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 Heights. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Shelter Island Heights, 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 Heights 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 Heights?

> [Silver Sands Motel & Beach Bungalows](https://www.expedia.ca/Greenport-Hotels-Silver-Sands.h91068954.Hotel-Information) is a 4-star hotel in Shelter Island Heights that's popular among Expedia travellers. Dining romance packages and pillow top mattresses are a couple of its amenities. Travellers also love [The Pridwin Hotel](https://www.expedia.ca/Shelter-Island-Heights-Hotels-The-Pridwin-Hotel.h6473437.Hotel-Information). From concierge services to massage services, it offers conveniences that cater to all aspects of your entertainment and relaxation.

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

> To find a 4-star hotel in Shelter Island Heights that fits your budget, take advantage of Expedia's handy filter tool. Browse the available options during your preferred dates and use our pricing filter to set your maximum rate. You can also sort your results by the most wallet-friendly option first.
> 
>   
> 
> -   Search for the lowest price from CA $573

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

> Treat yourself to luxury during your Shelter Island Heights escape by checking in to a 4-star hotel. As well as featuring upmarket surroundings, these retreats are typically packed with amenities like large beds, bathrobes and more. A 5-star hotel will go the extra mile to make your stay an even more indulgent and special one. Concierge assistance, elegant décor and gourmet dining are a few of the exclusive services and conveniences you'll likely have access to.

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-   [Houseboats in Shelter Island](https://www.expedia.ca/Shelter-Island-Houseboats.d157359-aaHouseboats.Travel-Guide-Accommodation)
-   [Resorts in Shelter Island](https://www.expedia.ca/Shelter-Island-Resort-Hotels.d157359-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 to Shelter Island](https://www.expedia.ca/Cheap-Flights-To-Shelter-Island.d157359.Travel-Guide-Flights)
-   [Flights from Shelter Island](https://www.expedia.ca/lp/flights/157359/flights-from-shelter-island)
-   [Flights from Southold](https://www.expedia.ca/lp/flights/183719/flights-from-southold)
-   [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 Shelter Island](https://www.expedia.ca/Shelter-Island.dx157359)

-   [Car rental Greenport](https://www.expedia.ca/Car-Rentals-In-Greenport.d110728.Car-Rental-Guide)
-   [Car rental Shelter Island](https://www.expedia.ca/Car-Rentals-In-Shelter-Island.d157359.Car-Rental-Guide)

-   [Shelter Island Vacation Rentals](https://www.expedia.ca/Shelter-Island-Vacation-Rentals.d157359.Travel-Guide-VacationRentals)

-   [Things to do in Greenport](https://www.expedia.ca/Things-To-Do-In-Greenport.d110728.Travel-Guide-Activities)
-   [Things to do in Shelter Island](https://www.expedia.ca/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities)

-   [Book 4 Star Hotels in Shelter Island Heights on Expedia.com](https://www.expedia.com/4Star-Shelter-Island-Heights-Hotels.s40-0-d183716.Travel-Guide-Filter-Hotels)