Title: 10 Best Town of Southold Town Luxury Resorts & Hotels for 2026 | Expedia.ca

[Town of Southold Town Travel Guide](https://expedia.ca/Town-Of-Southold-Town.dx553248635976002319)[Town of Southold Town Hotels](https://expedia.ca/Destinations-In-Town-Of-Southold-Town.d553248635976002319.Hotel-Destinations)[Vacation Rentals in Town of Southold Town](https://expedia.ca/Destinations-In-Town-Of-Southold-Town.d553248635976002319.Vacation-Rental-Destinations)[Town of Southold Town Car Rentals](https://expedia.ca/Destinations-In-Town-Of-Southold-Town.d553248635976002319.Car-Rental-Destinations)[Town of Southold Town Vacations](https://expedia.ca/Town-Of-Southold-Town.d553248635976002319.Destination-Travel-Guides)

![Lavender farm on Long Island ](https://images.trvl-media.com/place/6069914/ada6e93d-1aa6-4a8f-b17b-ce0cc0fcdf57.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by gavvykins

# Luxury Hotels & Resorts in Town of Southold Town

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## Top Cities in Town of Southold Town

![](https://mediaim.expedia.com/destination/2/9a9f855657c0f02d64549df7b59e54eb.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Greenport

[](https://expedia.ca/Greenport-Hotels-Luxury-Hotel.0-0-d110728-tLuxuryHotel.Travel-Guide-Filter-Hotels)

![](https://mediaim.expedia.com/destination/2/dff376d916af97d7b1d400e631f0d46e.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Cutchogue

[](https://expedia.ca/Cutchogue-Hotels-Luxury-Hotel.0-0-d183659-tLuxuryHotel.Travel-Guide-Filter-Hotels)

![](https://mediaim.expedia.com/destination/1/d3e06c642f947ddad6aebc58401dad70.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Orient

[](https://expedia.ca/Orient-Hotels-Luxury-Hotel.0-0-d6326191-tLuxuryHotel.Travel-Guide-Filter-Hotels)

![](https://mediaim.expedia.com/destination/2/c1e146be96c448a68862ae5f1f0cc1a9.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Peconic

[](https://expedia.ca/Peconic-Hotels-Luxury-Hotel.0-0-d144477-tLuxuryHotel.Travel-Guide-Filter-Hotels)

![](https://mediaim.expedia.com/destination/2/64a7a541b17dabdb743e9908dec5b467.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### East Marion

[](https://expedia.ca/East-Marion-Hotels-Luxury-Hotel.0-0-d6069914-tLuxuryHotel.Travel-Guide-Filter-Hotels)

## Check availability on Town of Southold Town Luxury Hotels

Tonight

[Dec 16 - Dec 17](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-12-16&endDate=2025-12-17&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property)

Tomorrow

[Dec 17 - Dec 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-12-17&endDate=2025-12-18&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property)

This weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-12-19&endDate=2025-12-21&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property)

Next weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-12-26&endDate=2025-12-28&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property)

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## Top Town of Southold Town Hotel Reviews

![Greenporter Hotel](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/3c3df51f_y.jpg)

### Greenporter Hotel

10/10 Excellent

"Comfy bed hot shower big room"

[](https://expedia.ca/Greenport-Hotels-Greenporter-Hotel.h90308554.Hotel-Information)

![The Shoals Suites and Slips](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/968755d8_y.jpg)

### The Shoals Suites and Slips

10/10 Excellent

"Great sta"

[](https://expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information)

![Silver Sands Motel & Beach Bungalows](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/52eefc00_y.jpg)

### Silver Sands Motel & Beach Bungalows

10/10 Excellent

"absolutely charming and totally bats above its weight. splurge for the bungalow!"

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

![The Harbor Front Inn](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca_y.jpg)

### The Harbor Front Inn

10/10 Excellent

"Yes"

[](https://expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information)

![The Menhaden](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/bc0d37bf_y.jpg)

### The Menhaden

10/10 Excellent

"Wonderful stay in a quaint hotel..The small town was amazing and had such cozy welcoming atmosphere! "

[](https://expedia.ca/Greenport-Hotels-The-Menhaden.h35229370.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)

![American Beech Hotel](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/0caf92d6_y.jpg)

### American Beech Hotel

10/10 Excellent

"Outstanding on all levels.. Hospitality and food top notch."

[](https://expedia.ca/Greenport-Hotels-American-Beech-Hotel.h11951124.Hotel-Information)

![Zey Hotel](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978_y.jpg)

### Zey Hotel

10/10 Excellent

"Not applicable "

[](https://expedia.ca/Greenport-Hotels-The-Gallery-Hotel.h15622089.Hotel-Information)

![The SandPiper ](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698318/9eada5e0_y.jpg)

### The SandPiper 

10/10 Excellent

"Unit was clean, inviting, and comfortable. We had a nice stay "

[](https://expedia.ca/Greenport-Hotels-The-SandPiper.h89698318.Hotel-Information)

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