Title: 10 Best Town of Southold Town Luxury Resorts & Hotels for 2025 | 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/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/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/2/64a7a541b17dabdb743e9908dec5b467.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

[Nov 12 - Nov 13](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-11-12&endDate=2025-11-13&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property)

Tomorrow

[Nov 13 - Nov 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-11-13&endDate=2025-11-14&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property)

This weekend

[Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-11-14&endDate=2025-11-16&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property)

Next weekend

[Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-11-21&endDate=2025-11-23&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property)

## Top Town of Southold Town Luxury Hotels

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## Top Town of Southold Town Hotel Reviews

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

### Zey Hotel

10/10 Excellent

"Staff was friendly, helpful and courteous. I loved the various options of sitting areas within the premises. "

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

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

### The Shoals Suites and Slips

10/10 Excellent

"This was a stunning place to stay in all respects. The large room was wonderrful. Thank you! "

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

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

### Sound View Greenport

10/10 Excellent

"Staff was amazing , room clean view phenomenal "

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

![Cliffside Resort Condominiums](//images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/1638a16b_y.jpg)

### Cliffside Resort Condominiums

10/10 Excellent

"Great stay - beautiful place"

[](https://expedia.ca/Greenport-Hotels-Cliffside-Resort-Condominiums.h10449005.Hotel-Information)

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

### The SandPiper

10/10 Excellent

"James was very helpful answering all questions. The Sandpiper was very clean and welcoming. We enjoyed our stay."

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

![Harbor Knoll Bed & Breakfast](//images.trvl-media.com/lodging/23000000/22810000/22804900/22804880/d47a17b9_y.jpg)

### Harbor Knoll Bed & Breakfast

10/10 Excellent

"fall season, pool not opened, been to Greenport before, weekends are best now, Halloween parade, plenty of small shops to peruse, bt check days and hours because of season"

[](https://expedia.ca/Greenport-Hotels-Harbor-Knoll-Bed-Breakfast.h22804880.Hotel-Information)

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

### Silver Sands Motel & Beach Bungalows

10/10 Excellent

"amazing stay, very quaint and relaxing "

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

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

### The Harbor Front Inn

10/10 Excellent

"Beautiful view and room. Staff friendly and accommodating. Excellent location. "

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

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

### The Menhaden

10/10 Excellent

"Hotel manager was great! Loved the firepits outside "

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

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

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