Title: Top Hotels in Town of Southold Town | Expedia.ca

  

[Town of Southold Town Travel Guide](https://expedia.ca/Town-Of-Southold-Town.dx553248635976002319)[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)

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# Search Town of Southold Town Hotels

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## Go beyond your typical stay in Town of Southold Town

Pet friendly

[](https://www.expedia.ca/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America&regionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2025-10-17&d1=2025-10-17&endDate=2025-10-19&d2=2025-10-19&amenities=PETS)

Apart hotel

[](https://www.expedia.ca/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America&regionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2025-10-17&d1=2025-10-17&endDate=2025-10-19&d2=2025-10-19&lodging=APART_HOTEL)

Spa

[](https://www.expedia.ca/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America&regionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2025-10-17&d1=2025-10-17&endDate=2025-10-19&d2=2025-10-19&amenities=SPA_ON_SITE)

Family friendly

[](https://www.expedia.ca/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America&regionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2025-10-17&d1=2025-10-17&endDate=2025-10-19&d2=2025-10-19&travelerType=family_friendly)

Pool

[](https://www.expedia.ca/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America&regionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2025-10-17&d1=2025-10-17&endDate=2025-10-19&d2=2025-10-19&amenities=POOL)

Ocean view

[](https://www.expedia.ca/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America&regionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2025-10-17&d1=2025-10-17&endDate=2025-10-19&d2=2025-10-19&amenities=OCEAN_VIEW)

Hot tub

[](https://www.expedia.ca/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America&regionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2025-10-17&d1=2025-10-17&endDate=2025-10-19&d2=2025-10-19&amenities=HOT_TUB)

Cabin

[](https://www.expedia.ca/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America&regionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2025-10-17&d1=2025-10-17&endDate=2025-10-19&d2=2025-10-19&lodging=CABIN)

Apart­ment

[](https://www.expedia.ca/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America&regionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2025-10-17&d1=2025-10-17&endDate=2025-10-19&d2=2025-10-19&lodging=APARTMENT)

Cottage

[](https://www.expedia.ca/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America&regionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2025-10-17&d1=2025-10-17&endDate=2025-10-19&d2=2025-10-19&lodging=COTTAGE)

Condo

[](https://www.expedia.ca/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America&regionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2025-10-17&d1=2025-10-17&endDate=2025-10-19&d2=2025-10-19&lodging=CONDO)

Waterpark

[](https://www.expedia.ca/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America&regionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2025-10-17&d1=2025-10-17&endDate=2025-10-19&d2=2025-10-19&amenities=WATER_PARK)

## 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.d110728.Travel-Guide-Hotels)

![](https://mediaim.expedia.com/destination/1/2af9844708ff5148df98a90729e7edaf.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Southold

[](https://expedia.ca/Southold-Hotels.d183719.Travel-Guide-Hotels)

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

#### Cutchogue

[](https://expedia.ca/Cutchogue-Hotels.d183659.Travel-Guide-Hotels)

![](https://mediaim.expedia.com/destination/2/b87fd2222bd9c0b45cd653e0605bfed5.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Mattituck

[](https://expedia.ca/Mattituck-Hotels.d6223780.Travel-Guide-Hotels)

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

#### Orient

[](https://expedia.ca/Orient-Hotels.d6326191.Travel-Guide-Hotels)

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

#### Peconic

[](https://expedia.ca/Peconic-Hotels.d144477.Travel-Guide-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.d6069914.Travel-Guide-Hotels)

![](https://mediaim.expedia.com/destination/2/f4b661641af8aca31895c5baaae02023.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Laurel

[](https://expedia.ca/Laurel-Hotels.d6131264.Travel-Guide-Hotels)

## Check prices for these dates

Tonight

[Oct 3 - Oct 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-10-03&endDate=2025-10-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 4 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-10-04&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Hotels in Town of Southold Town

![Property grounds](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/3c3df51f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/c7d19019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/c3d8e2ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/e78d099b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Greenporter Hotel

Greenport

9.2/10

Wonderful

(257)

"Staff was amazing and this hotel is in the perfect location "

CA $184

CA $211 total

includes taxes & fees

Oct 6 - Oct 7

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

![Deluxe Room, 2 Queen Beds](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/f76cf168.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)

### Sound View Greenport

Greenport

8.4/10

Very good

(574)

"Loved everything about my stay at the Sound view !! "

CA $347

CA $464 total

includes taxes & fees

Oct 27 - Oct 28

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

![One Bedroom Harbor View Terrace Suite | View from room](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Harbor View Balcony Junior Suite | Balcony view](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/e407cc6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Balcony view](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/64ea9871.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/a8d80546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Harbor Front Inn

Greenport

8.8/10

Excellent

(521)

"Great location ,beautiful hotel,nice staff"

CA $231

CA $332 total

includes taxes & fees

Nov 2 - Nov 3

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

![Exterior](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/bfb5cc4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/942c49f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden Suite, Wheelchair Accessible, Ground Floor, 2 Queen Beds, Non-Smoking](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/20957ef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Zey Hotel

Greenport

9.2/10

Wonderful

(275)

"Clean and quiet right on a main street with plenty of shopping and dining. Very close to the vineyards. Great stay."

CA $368

CA $420 total

includes taxes & fees

Oct 5 - Oct 6

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

![Garden Suite King](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/968755d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/81035eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Boardwalk Suite | Private kitchen](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/1898cf3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace King](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/efe41897.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Shoals Suites and Slips

Southold

9.6/10

Exceptional

(209)

"Great quick stay"

CA $311

CA $391 total

includes taxes & fees

Oct 6 - Oct 7

[](https://www.expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.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/c930d525.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)

![Waterfront Beach Shack Studio](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/65a8ebbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Silver Sands Motel & Beach Bungalows

Greenport

9.8/10

Exceptional

(132)

"Beautiful beach all was great, loved breakfast At on site diner Nookies!"

CA $364

CA $416 total

includes taxes & fees

Oct 6 - Oct 7

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

![Beach nearby](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/1638a16b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Condo | Living area](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/w1446h1293x1y0-077b519e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Condo](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/fa408cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Water Edge, First Floor, Corner | Living area](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/e745edd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cliffside Resort Condominiums

Greenport

9.0/10

Wonderful

(241)

"Great view of the water and nice amenities with the beach and pool."

CA $313

CA $418 total

includes taxes & fees

Nov 2 - Nov 3

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

![Property entrance](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/bc0d37bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast served](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/5b2ed019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sundeck](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/dc6eb455.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/f0f56ac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Menhaden

Greenport

9.6/10

Exceptional

(165)

"Loved the vineyards that a were a couple of miles away "

CA $431

CA $549 total

includes taxes & fees

Nov 3 - Nov 4

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

![Exterior](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/0caf92d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/9091cefd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed (#1)](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/339409ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/52855a41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### American Beech Hotel

Greenport

9.0/10

Wonderful

(193)

"The property was clean beautiful and pleasant. Loved the trendy decor."

CA $350

CA $456 total

includes taxes & fees

Oct 7 - Oct 8

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

![Interior entrance](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/a9ca389a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/63390424.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior detail](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/dd468523.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Porch](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/f10888a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vine & Sand

Southold

10/10

Exceptional

(11)

"We enjoyed an amazing wine weekend at Vine and Sand. Beautiful home and relaxing, enjoyable stay. Great location for visiting vineyards as well as the villages of Southold and Greenport. "

[](https://www.expedia.ca/Southold-Hotels-Vine-Sand.h96718085.Hotel-Information)

![Seasonal outdoor pool, open 8:00 AM to 7:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/92000000/91480000/91472700/91472602/48ec4beb.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/92000000/91480000/91472700/91472602/d6c9f61c.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/92000000/91480000/91472700/91472602/d7d73805.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/92000000/91480000/91472700/91472602/9b54ddd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Moraine

Greenport

9.8/10

Exceptional

(22)

"Our 3rd stay - we love the beauty of the property and the luxurious serenity of this boutique hotel. Great views of the water; fantastic large pool and lounging areas."

[](https://www.expedia.ca/Greenport-Hotels-Hotel-Moraine.h91472602.Hotel-Information)

![Beach/ocean view](https://images.trvl-media.com/lodging/2000000/1780000/1771100/1771009/d501821c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/2000000/1780000/1771100/1771009/0ec625aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/2000000/1780000/1771100/1771009/9698f5a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/2000000/1780000/1771100/1771009/8d30d692.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stirling House Bed & Breakfast

Greenport

9.8/10

Exceptional

(24)

"Our stay was only 2 nights but felt like 5. Well rested 3 days. Would return in a Heart Beat. Clay was awesome and the breakfasts were over the top !"

[](https://www.expedia.ca/Greenport-Hotels-Stirling-House-Bed-Breakfast.h1771009.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/11000000/10330000/10328200/10328173/c201860e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/11000000/10330000/10328200/10328173/5cc87916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/11000000/10330000/10328200/10328173/c8cd3b36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/11000000/10330000/10328200/10328173/204773b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Arbor View House B&B

East Marion

9.2/10

Wonderful

(15)

"Two mid age couples just had a good and relaxing time with great hospitality. "

[](https://www.expedia.ca/East-Marion-Hotels-Arbor-View-House-Bed-And-Breakfast.h10328173.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/23000000/22810000/22804900/22804880/d47a17b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach](https://images.trvl-media.com/lodging/23000000/22810000/22804900/22804880/f4e83179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/23000000/22810000/22804900/22804880/a22fa403.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/23000000/22810000/22804900/22804880/c17eac68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Harbor Knoll Bed & Breakfast

Pipes Cove

9.2/10

Wonderful

(11)

"It was very pleasant. We would stay again someday. Very convenient to restaurants in town and ferry. "

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

![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/0195b6df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/e69dbcaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/18f698b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/e500d985.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### American Beech in Greenport - Petite King Room 7

Greenport

9.0/10

Wonderful

(4)

"Great job "

CA $278

CA $428 total

includes taxes & fees

Oct 7 - Oct 8

[](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-Petite-King-Room-7.h71943248.Hotel-Information)

![Sun loungers, beach towels](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698360/91dd1778.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698360/dd4148b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698360/35ce389c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698360/6f8236be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### Aqua Vista

Pipes Cove

10/10

Exceptional

(20)

"Apartment was great for 2 couples and a baby. The location was amazing, 5 min walk to everything! Beds were super comfy!"

[](https://www.expedia.ca/Greenport-Hotels-Aqua-Vista.h89698360.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/103000000/102720000/102716900/102716809/b0e39c6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/103000000/102720000/102716900/102716809/w2160h1436x0y5-12097315.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/103000000/102720000/102716900/102716809/c1cf6b82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/103000000/102720000/102716900/102716809/w2160h1432x0y4-657cfcb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### Harbor Heights

Pipes Cove

9.8/10

Exceptional

(10)

"This was a perfect location and such a cute place! The apartment was spotless and well appointed. "

[](https://www.expedia.ca/Greenport-Hotels-Harbor-Heights.h102716809.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/37000000/36200000/36197500/36197422/7895e25e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/37000000/36200000/36197500/36197422/24a5012e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Boating](https://images.trvl-media.com/lodging/37000000/36200000/36197500/36197422/e31e9dc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/37000000/36200000/36197500/36197422/9f3c6fd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### White Blossom House Inn

Southold

10/10

Exceptional

(6)

"Mark and Mona were great hosts. The house and grounds were beautiful. Southold is a great town to explore and the house is close to the beach and the town. We loved the use of the bicycles which made our trip much more fun. We could ride to the beach, the town, and the wineries. Mona even pumped my bike tires before we went to explore. Thanks for a great time and we hope to be back again next year !"

[](https://www.expedia.ca/Southold-Hotels-White-Blossom-House-Inn.h36197422.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/10ef3e76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, video games, printers](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/30fcbecb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/a12114d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/52e5aba4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautifully farmhouse

Southold

10/10

Exceptional

(3)

"good experience"

CA $836

CA $1,637 total

includes taxes & fees

Oct 13 - Oct 14

[](https://www.expedia.ca/Southold-Hotels-Magic-Place.h113098265.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/36000000/35040000/35037700/35037604/2db832c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/36000000/35040000/35037700/35037604/fdf24660.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/36000000/35040000/35037700/35037604/123bbe23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/36000000/35040000/35037700/35037604/bc04c799.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

Peconic

9.6/10

Exceptional

(138)

"We had a wonderful stay at Andrew's house! The pool, hot tub, yard, and poolhouse are meticulously maintained. My 2 children (ages 2 and 4) loved their time in the pool, playing on the large lawn, and using the hammock. The house itself has a full kitchen and laundry with a large dining table great for a family. The location was beautiful--very close to wineries and lots of farmstands. We drove about 12 minutes to Greenport for an excellent dinner. Andrew was very friendly and helpful. ...

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

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-17&endDate=2025-10-18&regionId=553248635976002319&adults=2&sort=RECOMMENDED&openPlayBack=true)

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## Top Town of Southold Town Hotel Reviews

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

### Greenporter Hotel

10/10 Excellent

"Everything was in walking distance. Clean room"

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

"Great quick stay"

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

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

### Zey Hotel

10/10 Excellent

"Clean and quiet right on a main street with plenty of shopping and dining. Very close to the vineyards. Great stay."

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

"Quiet, nice, clean, friendly and helpful staff. It would have been nice if they had more avilable apps for streaming tv."

[](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

"We brought our bikes and the staff was very accommodating and helped us store them each night. We had a great time and will be back!"

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

![Harbor Heights ](//images.trvl-media.com/lodging/103000000/102720000/102716900/102716809/b0e39c6f_y.jpg)

### Harbor Heights

10/10 Excellent

"This was a perfect location and such a cute place! The apartment was spotless and well appointed. "

[](https://expedia.ca/Greenport-Hotels-Harbor-Heights.h102716809.Hotel-Information)

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

### Sound View Greenport

10/10 Excellent

"Clean and beautiful view"

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

!['The Gate House'on Beach front Estate with Dockage. Walk to Village .](//images.trvl-media.com/lodging/35000000/34210000/34201400/34201329/89437aaa_y.jpg)

### 'The Gate House'on Beach front Estate with Dockage. Walk to Village .

10/10 Excellent

"This was the perfect long weekend getaway. The location is unbeatable. Downtown was just a five minute drive and the beach was just a few steps from our house. Communication with our host was excellent and the house was very clean and exactly as described. We took advantage of the charcoal grill every night. For children, there’s a beautiful waterfront playground nearby, a carousel downtown and a miniature train ride just a few minutes away. While it is described in the listing, I would just note that there are multiple homes on the property (3 or 4, I think). They are well spaced and you do have your privacy but it is worth noting. This didn’t make a difference to my family and I as we are already planning our next return. "

[](https://expedia.ca/Greenport-Hotels-The-Gate-Houseon-Beach-Front-Estate-With-Dockage-Walk-To-Village.h34201329.Hotel-Information)

![Vine & Sand](//images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/a9ca389a_y.jpg)

### Vine & Sand

10/10 Excellent

"Amazing hospitality, high end linens, conveniently stocked fridge / pantry. Peaceful and relaxing for an anniversary weekend. Rooms are beautiful, location is central to wineries and a gorgeous bay beach. Highly recommend!"

[](https://expedia.ca/Southold-Hotels-Vine-Sand.h96718085.Hotel-Information)

## Explore a world of travel with Expedia

-   Explore a world of travel with Expedia

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### Explore more hotels

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[See a list of all hotels in Town of Southold Town](https://expedia.ca/All-Town-Of-Southold-Town-Hotels.d553248635976002319.Travel-Guide-City-All-Hotels)

### More ways to book

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-   [Hotels in Upper West Side](https://expedia.ca/Upper-West-Side-New-York-Hotels.0-n800075-0.Travel-Guide-Filter-Hotels)
-   [Hotels in Downtown Buffalo](https://expedia.ca/Downtown-Buffalo-Buffalo-Hotels.0-n6056533-0.Travel-Guide-Filter-Hotels)
-   [Hotels in SoHo](https://expedia.ca/SoHo-New-York-Hotels.0-n6142503-0.Travel-Guide-Filter-Hotels)

Cars

-   [Car rental New York Airport (JFK)](https://expedia.ca/Car-Rentals-In-John-F-Kennedy-Intl.d4933194.Car-Rental-Guide)
-   [Car rental New York Airport (LGA)](https://expedia.ca/Car-Rentals-In-LaGuardia.d4278092.Car-Rental-Guide)

Packages

-   [Statue of Liberty](https://expedia.ca/Statue-Of-Liberty-New-York.d502066.Vacation-Attraction)
-   [Brooklyn Bridge](https://expedia.ca/Brooklyn-Bridge-New-York.d6065311.Vacation-Attraction)
-   [Walden Galleria Mall](https://expedia.ca/Walden-Galleria-Mall-Buffalo.d6129205.Vacation-Attraction)

General

-   [Visit Downtown Buffalo](https://expedia.ca/Buffalo-Downtown-Buffalo.dx6056533)
-   [Visit Downtown Niagara Falls](https://expedia.ca/Niagara-Falls-Downtown-Niagara-Falls.dx553248633938968497)
-   [Visit Greenwich Village](https://expedia.ca/New-York-Greenwich-Village.dx110832)

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![QR code to download the app](data:image/png;base64,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)