Title: 4 Stars Hotels in Southold, New York from CA $324 - Find Cheap Southold Hotels With 4 Stars | Expedia.ca

 

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![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

# 4 Stars Hotels in Southold, New York from CA $324

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## Check availability on Southold 4 Star Hotels

Tonight

[Dec 2 - Dec 3](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-12-02&endDate=2025-12-03&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 3 - Dec 4](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-12-03&endDate=2025-12-04&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-12-05&endDate=2025-12-07&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-12-12&endDate=2025-12-14&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Southold 4 Star Hotels

![Exterior](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/18df186b.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)

![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)

### Madison Beach Hotel

Madison Center

9.4/10

Exceptional

(339)

"Staff and hotel are lovely "

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

Steven

CA $343

CA $394 total

includes taxes & fees

Jan 2 - Jan 3, 2026

[](https://www.expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.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/16000000/15280000/15273200/15273178/55b708b5.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)

![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)

### Sound View Greenport

Greenport

8.6/10

Excellent

(596)

"Staff was amazing , room clean view phenomenal "

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

Denise

CA $224

CA $324 total

includes taxes & fees

Dec 7 - Dec 8

[](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)

![Executive Cottage](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/6d8b086b.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 Suite](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/9bf97ebb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Canoe Place Inn and Cottages

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)

![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)

![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

(159)

"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 $260

CA $326 total

includes taxes & fees

Dec 9 - Dec 10

[](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)

![Premium bedding, down comforters, pillowtop beds, minibar](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/a413ef5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Waterfront Beach Shack Studio | View from room](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/8f5285b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach Shack w/ Sleeping Alcove](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/b99eb106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Silver Sands Motel & Beach Bungalows

Greenport

9.8/10

Exceptional

(139)

"amazing stay, very quaint and relaxing "

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

rebecca

[](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)

![Bicycling](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/65a49724.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/c6fa26de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Roundtree, Amagansett

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 $832

CA $998 total

includes taxes & fees

Jan 1 - Jan 2, 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)

![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)

![Exterior](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/a99c206a.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)

### Copper Beech Inn

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 $390

CA $448 total

includes taxes & fees

Dec 3 - Dec 4

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

![Garden](https://images.trvl-media.com/lodging/2000000/1090000/1085700/1085655/3e8af6f2.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)

### The 1770 House Restaurant & Inn

East Hampton

9.8/10

Exceptional

(160)

"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 $372

CA $508 total

includes taxes & fees

Dec 3 - Dec 4

[](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/e9d81899.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)

![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)

### Topping Rose House

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 $719

CA $827 total

includes taxes & fees

Jan 2 - Jan 3, 2026

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

![Garden](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/32700dd1.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)

![Lobby sitting area](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/a9768080.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/5021abf5.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 $352

CA $403 total

includes taxes & fees

Jan 2 - Jan 3, 2026

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

![Front of property](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/0122d57a.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

(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)

![Garden](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/9d3a1088.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Master Guest Room](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/90421aa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### East Hampton Art House Bed & Breakfast

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 $549

CA $628 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](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)

![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)

![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)

### James Pharmacy Bed & Breakfast

Old Saybrook Center

9.2/10

Wonderful

(21)

"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 $422

CA $469 total

includes taxes & fees

Dec 21 - Dec 22

[](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/w860h368x0y0-6172fc5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/90000000/89990000/89981800/89981758/3e9b9c2a.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)

![Exterior](https://images.trvl-media.com/lodging/90000000/89990000/89981800/89981758/0dd69505.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Rams Head Inn

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)

![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)

![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

Hampton Bays

10/10

Exceptional

(1)

CA $2,194

CA $2,658 total

includes taxes & fees

Dec 31 - Jan 1, 2026

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

![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)

![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

Sag Harbor

9.0/10

Wonderful

(292)

"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)

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

![Property grounds](https://images.trvl-media.com/lodging/13000000/12780000/12779400/12779331/b79b89fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Gazebo](https://images.trvl-media.com/lodging/13000000/12780000/12779400/12779331/f42806db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily full breakfast](https://images.trvl-media.com/lodging/13000000/12780000/12779400/12779331/175e4715.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 434 on Main

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)

![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)

![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)

![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)

"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)

![Interior](https://images.trvl-media.com/lodging/36000000/35040000/35037700/35037604/6d9b2b35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/36000000/35040000/35037700/35037604/7dfc3af5.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/a2a9dc3f.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)

### Historic House Getaway

Peconic

9.6/10

Exceptional

(139)

"Great location. Host was was excellent getting any information I need. Clean, nice for our family. Swimming pool and hot tub was nice and clean."

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

Nathan L.

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

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

![Garden](https://images.trvl-media.com/lodging/91000000/90790000/90786400/90786314/71becd12.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/91000000/90790000/90786400/90786314/7187781f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Farmhouse Bed and Breakfast

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)

![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg)

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 Southold.

![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 $419

CA $527 total

Dec 22 - Dec 23

includes taxes & fees

9/10 Wonderful! (73 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=16%2F12%2F2025&endDate=17%2F12%2F2025&selected=32411044&PinnedHotelID=32411044&HadPinnedHotel=true&regionId=183719)

[](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 Southold.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F12%2F2025&endDate=04%2F12%2F2025&regionId=183719&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=03%2F12%2F2025&endDate=04%2F12%2F2025&regionId=183719&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F12%2F2025&endDate=04%2F12%2F2025&regionId=183719&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F12%2F2025&endDate=04%2F12%2F2025&regionId=183719&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F12%2F2025&endDate=04%2F12%2F2025&regionId=183719&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F12%2F2025&endDate=04%2F12%2F2025&regionId=183719&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 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=2025-12-16&endDate=2025-12-17&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/b52e0fa4_y.jpg)

### Sound View Greenport

10/10 Excellent

"The room was very clean, bed was comfy, and the sounds of the water outside were lovely. I did arrive very late and all parking spots were taken which was sort of inconvenient as it is a bit of a walk to park by other rooms. Check in process was super smooth."

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

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

### Madison Beach Hotel

10/10 Excellent

"Great 1st wedding anniversary experience!"

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

> Kick back and unwind in 4-star hotel comfort at [Sound View Greenport](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information). Ranked highly by many of our guests, it features concierge services and a terrace. Also take a look at [The Pridwin Hotel](https://www.expedia.ca/Shelter-Island-Heights-Hotels-The-Pridwin-Hotel.h6473437.Hotel-Information). Concierge services and massage services make this retreat another sought-after choice in Southold.

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

> To book a 4-star hotel in Southold that matches your budget, take advantage of Expedia's handy filter tool. Check out the availability during your vacation dates and use our pricing filter to set your maximum rate. You can also sort your results by the most affordable property first.
> 
>   
> 
> -   Search for the lowest price from CA $527

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

> Treat yourself to luxury living during your Southold getaway by staying at a 4-star hotel. As well as featuring upscale surroundings, these properties are usually packed with amenities like large beds, bathrobes and plenty more. A 5-star hotel will go the extra mile to make your stay an even more indulgent and memorable one. Concierge assistance, elegant décor and gourmet dining are only the start of the first-rate conveniences and services you'll likely have access to.

## Explore a world of travel with Expedia

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-   [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)
-   [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)

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

-   [Bedell Cellars](https://www.expedia.ca/Bedell-Cellars-Cutchogue.d553248621532665643.Vacation-Attraction)
-   [Visit Pipes Cove](https://www.expedia.ca/Greenport-Pipes-Cove.dx553248635976473295)
-   [Pindar Vineyards](https://www.expedia.ca/Pindar-Vineyards-Peconic.d6326965.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)
-   [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 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 Southold on Expedia.com](https://www.expedia.com/4Star-Southold-Hotels.s40-0-d183719.Travel-Guide-Filter-Hotels)