Title: Top Guest Houses in  Town of Southold Town in 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

# Guest Houses in Town of Southold Town

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## Check prices for these dates

Next weekend

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2026-01-09&endDate=2026-01-11&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2026-02-27&endDate=2026-03-01&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## 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-Guest-Houses.d110728-aaGuestHouses.Travel-Guide-Accommodation)

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

#### Cutchogue

[](https://expedia.ca/Cutchogue-Guest-Houses.d183659-aaGuestHouses.Travel-Guide-Accommodation)

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

#### Southold

[](https://expedia.ca/Southold-Guest-Houses.d183719-aaGuestHouses.Travel-Guide-Accommodation)

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

#### Mattituck

[](https://expedia.ca/Mattituck-Guest-Houses.d6223780-aaGuestHouses.Travel-Guide-Accommodation)

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

#### Orient

[](https://expedia.ca/Orient-Guest-Houses.d6326191-aaGuestHouses.Travel-Guide-Accommodation)

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

#### Peconic

[](https://expedia.ca/Peconic-Guest-Houses.d144477-aaGuestHouses.Travel-Guide-Accommodation)

## Our top choices for Town of Southold Town guest houses

![Romantic House, 4 Bedrooms, Kitchen, Garden View | Terrace/patio](https://images.trvl-media.com/lodging/28000000/27180000/27172100/27172022/fcd9b598.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Romantic House, 4 Bedrooms, Kitchen, Garden View | Private kitchen](https://images.trvl-media.com/lodging/28000000/27180000/27172100/27172022/1a1bc9e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Romantic House, 4 Bedrooms, Kitchen, Garden View](https://images.trvl-media.com/lodging/28000000/27180000/27172100/27172022/5dd0697c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV, fireplace](https://images.trvl-media.com/lodging/28000000/27180000/27172100/27172022/818430cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Victorian Seasons Stirling

[](https://www.expedia.ca/Greenport-Hotels-Victorian-Seasons-Stirling.h27172022.Hotel-Information)

Greenport

[](https://www.expedia.ca/Greenport-Hotels-Victorian-Seasons-Stirling.h27172022.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.

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## Top Town of Southold Town Hotel Reviews

![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

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

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

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

### The Menhaden

10/10 Excellent

"Front desk staff was outstanding. So helpful with all types of suggestions from dining to wineries and general property amenities. Room as beautiful and spotless. Bed was quite comfortable. Lounge/ bar was so convenient. Great location in town too. "

[](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

"Nice place"

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

"Great check in experience. Very nice room"

[](https://expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.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 stay, will definitely go again"

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

![“Paradise Found” - Walk to Private Beach & In-Ground Pool!](https://images.trvl-media.com/lodging/109000000/108600000/108598500/108598430/daa9d409_y.jpg)

### “Paradise Found” - Walk to Private Beach & In-Ground Pool!

10/10 Excellent

"We had a great stay. We enjoyed cooking in the beautiful kitchen and spending time with family. We hope to visit again!"

[](https://expedia.ca/Southold-Hotels-North-Fork-Dream-Getaway-Walk-To-Private-Beach-NEW-In-Ground-Pool.h108598430.Hotel-Information)

![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)

![Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698399/w906h683x59y0-97f670df_y.jpg)

### Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

10/10 Excellent

"Good communication. Clean & well stocked. "

[](https://expedia.ca/Greenport-Hotels-Blue-Bay-Dream.h89698399.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)

## Find out more about Town of Southold Town

## Town of Southold Town Guest Houses information

| Number of reviews |                |
| ----------------- | -------------- |
| Accommodation     | 1 Guest Houses |
| Lowest Price      |                |
| Highest Price     |                |

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- [Flights from Shelter Island ](https://www.expedia.ca/lp/flights/157359/flights-from-shelter-island)
- [Flights from Southold ](https://www.expedia.ca/lp/flights/183719/flights-from-southold)
- [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)