Title: 4 Stars Hotels in Dering Harbor, Shelter Island from CA $317 - Find Cheap Dering Harbor Hotels With 4 Stars | Expedia.ca

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# 4 Stars Hotels in Dering Harbor, Shelter Island from CA $317

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## Check availability on Dering Harbor 4 Star Hotels

Tonight

[Dec 23 - Dec 24](https://www.expedia.ca/Hotel-Search?regionId=553248634998885605&startDate=2025-12-23&endDate=2025-12-24&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 24 - Dec 25](https://www.expedia.ca/Hotel-Search?regionId=553248634998885605&startDate=2025-12-24&endDate=2025-12-25&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248634998885605&startDate=2025-12-26&endDate=2025-12-28&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248634998885605&startDate=2026-01-02&endDate=2026-01-04&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Dering Harbor 4-star hotels

![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)

![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 | View from room](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/79675399.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

(341)

"The Spa was wonderful and the staff was attentive and helpful. "

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

Emma

CA $338

CA $388 total

includes taxes & fees

Jan 1 - Jan 2, 2026

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

![Yoga](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/a7c5a78c.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)

![Exterior](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/8a4a605e.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

8.6/10

Excellent

(599)

"Staff was amazing , room clean view phenomenal "

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

Denise

CA $219

CA $317 total

includes taxes & fees

Dec 24 - Dec 25

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

![Couples treatment rooms, body treatments, hot stone massages](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/1782c2d9.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)

![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)

### 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

(60)

"Amazing property. Really enjoyed our stay."

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

Dave

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

![Suite, 1 King Bed with Sofa bed](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/7418aad9.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

9.0/10

Wonderful

(160)

"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

[](https://www.expedia.ca/East-Hampton-Hotels-Journey-East-Hampton.h23252049.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/92000000/91070000/91069000/91068954/1c4953c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![43-inch Smart TV with digital channels, Netflix, Hulu](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/cc998cf2_edited_ffd0.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)

### Silver Sands Motel & Beach Bungalows

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

Greenport

9.8/10

Exceptional

(142)

"Great get away "

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

Charles

[](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/11000000/10550000/10547800/10547745/028711b6.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)

![Frette Italian sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/a3bdf0f5.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

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

Amagansett North

10/10

Exceptional

(91)

"Located right in the center of town, the grounds on this property are wonderful with clean and comfortable suites. The staff are engaging and sweet. And the late night cookies are a sweet touch."

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

adam

CA $817

CA $980 total

includes taxes & fees

Jan 11 - Jan 12, 2026

[](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)

![Interior entrance](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/98c270a2.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 314)](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/61b576aa.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

(506)

"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 $384

CA $441 total

includes taxes & fees

Dec 24 - Dec 25

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

![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)

![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/2000000/1090000/1085700/1085655/67db121e.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

(161)

"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 $380

CA $519 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/East-Hampton-Hotels-The-1770-House-Restaurant-Inn.h1085655.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/6000000/5590000/5581400/5581380/9423d3da.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)

![Library](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/88ff99e0.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

(136)

"Great rooms, staff and food"

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

Alexandra

CA $648

CA $746 total

includes taxes & fees

Jan 2 - Jan 3, 2026

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

![Exterior detail](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/32e03a99.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)

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

### The Maidstone

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

East Hampton

8.0/10

Very good

(150)

"We had a wonderful stay "

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

Sabrina

CA $314

CA $359 total

includes taxes & fees

Dec 28 - Dec 29

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

![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)

![Breakfast, lunch, dinner served; local cuisine, ocean views ](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/w2880h1617x0y0-215d1f51.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)

"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)

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

![Interior](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/e8a2f490.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)

![Exterior](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/bbbb0bf2.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)

"Roz and Michael built a beautiful paradise that they enjoy sharing with you. Everything is amazing. "

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

Dan

CA $541

CA $618 total

includes taxes & fees

Dec 25 - Dec 26

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

![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/f09f38b4.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)

"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

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

"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)

![Private kitchen](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/1190496c.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)

![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)

### Canoe Place Waterfront Residences

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

Hampton Bays

10/10

Exceptional

(1)

CA $2,616

CA $3,169 total

includes taxes & fees

Dec 24 - Dec 25

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

![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)

![Restaurant](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148848/94958fa7.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)

"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)

![Reception hall](https://images.trvl-media.com/lodging/13000000/12780000/12779400/12779331/59df497c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/13000000/12780000/12779400/12779331/2c06a5e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/13000000/12780000/12779400/12779331/7e250b31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/13000000/12780000/12779400/12779331/3583b9cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 434 on Main

[](https://www.expedia.ca/Amagansett-Hotels-434-On-Main.h12779331.Hotel-Information)

Amagansett North

10/10

Exceptional

(36)

"Great hosts"

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

David

[](https://www.expedia.ca/Amagansett-Hotels-434-On-Main.h12779331.Hotel-Information)

![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)

![Interior](https://images.trvl-media.com/lodging/54000000/53900000/53890800/53890717/5ff0ea97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![6 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/54000000/53900000/53890800/53890717/e2fe4315.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/54000000/53900000/53890800/53890717/367ac402_edited_0ea9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Sag Harbor

10/10

Exceptional

(11)

"Great house, close to the town, would definitely rent again "

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

Jared W.

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35040000/35037700/35037604/3c3104d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/36000000/35040000/35037700/35037604/094d4d1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/36000000/35040000/35037700/35037604/4e0330ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35040000/35037700/35037604/bc698802.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic House Getaway

[](https://www.expedia.ca/Peconic-Hotels-NORTHFORK-COTTAGE-With-POOL-HOTTUB.h35037604.Hotel-Information)

Peconic

9.6/10

Exceptional

(139)

"Friends enjoyed the pool and jacuzzi and liked the house"

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

Fionan M.

[](https://www.expedia.ca/Peconic-Hotels-NORTHFORK-COTTAGE-With-POOL-HOTTUB.h35037604.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/91000000/90790000/90786400/90786314/07d5462f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/91000000/90790000/90786400/90786314/f2989301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90790000/90786400/90786314/6bd86bf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Romantic Room](https://images.trvl-media.com/lodging/91000000/90790000/90786400/90786314/06263549.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Farmhouse Bed and Breakfast

[](https://www.expedia.ca/Cutchogue-Hotels-The-Farmhouse-Bed-And-Breakfast.h90786314.Hotel-Information)

Cutchogue

10/10

Exceptional

(13)

"very comfortable stay. "

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

Valentine

[](https://www.expedia.ca/Cutchogue-Hotels-The-Farmhouse-Bed-And-Breakfast.h90786314.Hotel-Information)

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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 Dering Harbor.

![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 $516

CA $907 total

Dec 29 - Dec 30

includes taxes & fees

9/10 Wonderful! (75 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=06%2F01%2F2026&endDate=07%2F01%2F2026&selected=32411044&PinnedHotelID=32411044&HadPinnedHotel=true&regionId=553248634998885605)

[](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 Dering Harbor.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=24%2F12%2F2025&endDate=25%2F12%2F2025&regionId=553248634998885605&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=24%2F12%2F2025&endDate=25%2F12%2F2025&regionId=553248634998885605&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=24%2F12%2F2025&endDate=25%2F12%2F2025&regionId=553248634998885605&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=24%2F12%2F2025&endDate=25%2F12%2F2025&regionId=553248634998885605&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=24%2F12%2F2025&endDate=25%2F12%2F2025&regionId=553248634998885605&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=24%2F12%2F2025&endDate=25%2F12%2F2025&regionId=553248634998885605&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.

## Top Dering Harbor Hotel Reviews

![Madison Beach Hotel](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/18df186b_y.jpg)

### Madison Beach Hotel

10/10 Excellent

"beautiful room and views"

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

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

### Sound View Greenport

10/10 Excellent

"Great room with amazing views! Staff was fantastic and the food was great too"

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

## Find out more about Dering Harbor

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 Dering Harbor are calling your name. Known for providing first-rate service in amazing locations, each of the Dering Harbor 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 Dering Harbor. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Dering Harbor, Shelter Island, 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 Dering Harbor hotels with 4 Stars provide everything you need to unwind in style.

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- [Silver Beach Hotels ](https://www.expedia.ca/Silver-Beach-Shelter-Island-Hotels.0-n553248635976481903-0.Travel-Guide-Filter-Hotels)
- [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)

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- [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)
- [Shelter Island Heights Vacations ](https://www.expedia.ca/Shelter-Island-Heights.d183716.Destination-Travel-Guides)
- [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)
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- [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 Heights ](https://www.expedia.ca/Things-To-Do-In-Shelter-Island-Heights.d183716.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 Dering Harbor on Expedia.com ](https://www.expedia.com/4Star-Dering-Harbor-Hotels.s40-0-d553248634998885605.Travel-Guide-Filter-Hotels)