Title: 4 Stars Hotels in Southold, New York from CA $257 - Find Cheap Southold Hotels With 4 Stars | Expedia.ca

[Southold Travel Guide](https://expedia.ca/Southold.dx183719)[Hotels in Southold](https://expedia.ca/Southold-Hotels.d183719.Travel-Guide-Hotels)[Vacation Rentals in Southold](https://expedia.ca/Southold-Vacation-Rentals.d183719.Travel-Guide-VacationRentals)[Flights to Southold](https://expedia.ca/Cheap-Flights-To-Southold.d183719.Travel-Guide-Flights)[Things to do in Southold](https://expedia.ca/Things-To-Do-In-Southold.d183719.Travel-Guide-Activities)[Southold Car Rentals](https://expedia.ca/Car-Rentals-In-Southold.d183719.Car-Rental-Guide)[Southold Vacation Packages](https://expedia.ca/Southold.d183719.Destination-Travel-Guides)

![Day trip to North Fork wineries. Stopped at this beach for a break before driving back to the city. #sunset #nature #wanderlust #waterlust #beach #colorful #citylife #NikonD7100 #Manfratto tripod. ](https://images.trvl-media.com/place/183719/81468873-e891-4a92-aa0d-1938572ea198.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Benny Goh 

![](https://images.trvl-media.com/place/183719/81468873-e891-4a92-aa0d-1938572ea198.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check availability on Southold 4 Star Hotels

Tonight

[Mar 11 - Mar 12](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-03-11&endDate=2026-03-12&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Mar 12 - Mar 13](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-03-12&endDate=2026-03-13&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-03-13&endDate=2026-03-15&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-03-20&endDate=2026-03-22&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Southold 4-star hotels

![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

8.4/10

Very good

(620 reviews)

"Nice place"

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

Mateusz

CA $191

CA $257 total

includes taxes & fees

Mar 12 - Mar 13

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

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

![Private beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/c4093211.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

### Madison Beach Hotel

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

Madison Center

9.4/10

Exceptional

(347 reviews)

"Staff and hotel are lovely "

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

Steven

CA $300

CA $345 total

includes taxes & fees

Mar 31 - Apr 1

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

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

![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)

![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)

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

### Journey East Hampton

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

East Hampton North

9.2/10

Wonderful

(164 reviews)

"Amazing stay"

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

Liana

CA $237

CA $297 total

includes taxes & fees

Mar 22 - Mar 23

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

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

![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)

![Bar (on property)](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/968c61db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Maidstone

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

East Hampton

8.0/10

Very good

(152 reviews)

"We had a wonderful stay "

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

Sabrina

CA $325

CA $372 total

includes taxes & fees

Mar 30 - Mar 31

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

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

![Exterior](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/9423d3da.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)

![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

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

Bridgehampton

9.2/10

Wonderful

(143 reviews)

"Our second home :)"

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

olivia

CA $727

CA $836 total

includes taxes & fees

Mar 12 - Mar 13

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

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

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

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

![View from room](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/2d824970.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

(148 reviews)

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

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

Dan

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

![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

(162 reviews)

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

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

Anthony

CA $361

CA $493 total

includes taxes & fees

Mar 12 - Mar 13

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

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

![Aerial view](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/56f0c16b.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/11000000/10550000/10547800/10547745/06408853.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

(93 reviews)

"Fantastic hotel, great location."

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

Tunca

CA $807

CA $968 total

includes taxes & fees

Mar 12 - Mar 13

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

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

![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)

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/f53e135a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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 reviews)

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

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

Dianne

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

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

![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)

![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)

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

### James Pharmacy Bed & Breakfast

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

Old Saybrook Center

9.0/10

Wonderful

(23 reviews)

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

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

Isolde

CA $410

CA $455 total

includes taxes & fees

Apr 1 - Apr 2

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

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

![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/e11ede87.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

(509 reviews)

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

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

Marilyn

CA $379

CA $436 total

includes taxes & fees

Mar 12 - Mar 13

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

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

![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)

![Bicycling](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/6893dda0.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)

### Canoe Place Inn and Cottages

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

Hampton Bays

9.8/10

Exceptional

(62 reviews)

"Wonderful stay! "

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

Lindsay

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

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

![Exterior](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148848/c880734c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

### Faraway Sag Harbor

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

Sag Harbor

9.0/10

Wonderful

(292 reviews)

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

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

Michael

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

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

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

![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 review)

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

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

![Restaurant](https://images.trvl-media.com/lodging/90000000/89990000/89981800/89981758/w1170h1461x0y0-bc75bc71.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)

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

### The Rams Head Inn

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

Shelter Island Heights

7.6/10

Good

(18 reviews)

"Beautiful views and lovely service "

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

Lana

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

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

![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)

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

### East Hampton Art House Bed & Breakfast

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

Clearwater Beach

9.6/10

Exceptional

(65 reviews)

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

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

IVAN

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

![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)

![Dining](https://images.trvl-media.com/lodging/13000000/12780000/12779400/12779331/8bb0df98.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

(37 reviews)

"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)

![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)

![Romantic Room](https://images.trvl-media.com/lodging/91000000/90790000/90786400/90786314/06263549.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)

![Living area](https://images.trvl-media.com/lodging/91000000/90790000/90786400/90786314/f2989301.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 reviews)

"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)

![Front of property](https://images.trvl-media.com/lodging/10000000/9510000/9502700/9502687/a8be7dae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily full breakfast](https://images.trvl-media.com/lodging/10000000/9510000/9502700/9502687/0391054f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; alfresco dining](https://images.trvl-media.com/lodging/10000000/9510000/9502700/9502687/a7f2bde7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Gazebo](https://images.trvl-media.com/lodging/10000000/9510000/9502700/9502687/7165a72d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Jedediah Hawkins Inn

[](https://www.expedia.ca/Riverhead-Hotels-Jedediah-Hawkins-Inn.h9502687.Hotel-Information)

Jamesport

9.8/10

Exceptional

(18 reviews)

"It was our first time in this hotel and the area,it was very relaxing. Great service"

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

OMAR

[](https://www.expedia.ca/Riverhead-Hotels-Jedediah-Hawkins-Inn.h9502687.Hotel-Information)

![House, Multiple Beds (Quogue Contemporary) | Pool](https://images.trvl-media.com/lodging/84000000/83760000/83758500/83758407/17c21c77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, Multiple Beds (Quogue Contemporary)](https://images.trvl-media.com/lodging/84000000/83760000/83758500/83758407/c8de2d56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, Multiple Beds (Quogue Contemporary) | Private kitchen](https://images.trvl-media.com/lodging/84000000/83760000/83758500/83758407/82aaa9dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, Multiple Beds (Quogue Contemporary) | Living room](https://images.trvl-media.com/lodging/84000000/83760000/83758500/83758407/1a2bf869.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quogue Contemporary

[](https://www.expedia.ca/East-Quogue-Hotels-Quogue-Contemporary.h83758407.Hotel-Information)

East Quogue

[](https://www.expedia.ca/East-Quogue-Hotels-Quogue-Contemporary.h83758407.Hotel-Information)

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## Learn more about Southold

Vineyards and farm stands dot the landscape of this North Fork gem, inviting visitors to sample local wines and fresh produce. Stroll along the pebble beaches, explore historic lighthouses, or take a ferry to nearby Shelter Island for a day trip.

[See all hotels in Southold](https://www.expedia.ca/Hotel-Search?startDate=2026-03-25&endDate=2026-03-26&adults=2&regionId=183719)

![Day trip to North Fork wineries. Stopped at this beach for a break before driving back to the city. #sunset #nature #wanderlust #waterlust #beach #colorful #citylife #NikonD7100 #Manfratto tripod. ](https://images.trvl-media.com/place/183719/81468873-e891-4a92-aa0d-1938572ea198.jpg?impolicy=fcrop&w=899&h=600&p=1&q=high)

Photo by Benny Goh 

## Top Southold Hotel Reviews

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

### Sound View Greenport

10/10 Excellent

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

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

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

### Journey East Hampton

10/10 Excellent

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

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

## Find out more about Southold

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

## Frequently asked questions

### What are the best 4-star hotels in Southold?

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

> - Search for the lowest price from CA $257

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

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