Title: Town of Southold Town Vacation Home Rentals from CA $274: Search Top Private Vacation Homes for Rent | 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)

![August on Long Island brings the beautiful color of the sunflower fields on the east end of Long Island NY.  Acres and acres of fields in bloom and with the setting sun, it is breathtaking. 

People travel for miles to reach the various fields. This on is at the North Fork Potato chip Company and they time the sunflowers so fields are in bloom through September. 

East end north fork is always a treat for the eyes. old farms and quaint villages. ](https://images.trvl-media.com/place/6223780/98d7170c-1a29-406f-b729-090d5ee87ea6.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Jan Shannon

![](https://images.trvl-media.com/place/6223780/98d7170c-1a29-406f-b729-090d5ee87ea6.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=553248635976002319&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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-Private-Vacation-Homes.d110728-aaPrivateVacationHomes.Travel-Guide-Accommodation)

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

#### Cutchogue

[](https://expedia.ca/Cutchogue-Private-Vacation-Homes.d183659-aaPrivateVacationHomes.Travel-Guide-Accommodation)

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

#### Southold

[](https://expedia.ca/Southold-Private-Vacation-Homes.d183719-aaPrivateVacationHomes.Travel-Guide-Accommodation)

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

#### Mattituck

[](https://expedia.ca/Mattituck-Private-Vacation-Homes.d6223780-aaPrivateVacationHomes.Travel-Guide-Accommodation)

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

#### Orient

[](https://expedia.ca/Orient-Private-Vacation-Homes.d6326191-aaPrivateVacationHomes.Travel-Guide-Accommodation)

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

#### Peconic

[](https://expedia.ca/Peconic-Private-Vacation-Homes.d144477-aaPrivateVacationHomes.Travel-Guide-Accommodation)

## Our top choices for Town of Southold Town vacation homes

![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)

![Exterior detail](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698360/6f8236be.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698360/9a9ba36d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Pipes Cove

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

10/10

Exceptional

(24 reviews)

"Great location and perfect for two couples. We loved staying here."

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

laura d.

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

![Dining](https://images.trvl-media.com/lodging/119000000/118740000/118737900/118737819/daa7ee88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/119000000/118740000/118737900/118737819/5a3c3005.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/119000000/118740000/118737900/118737819/af3b4415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/119000000/118740000/118737900/118737819/516072be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Peconic

[](https://www.expedia.ca/Peconic-Hotels-Newly-Renovated.h118737819.Hotel-Information)

10/10

Exceptional

(2 reviews)

"This was a perfect home base for our 40th birthday weekend. Great space and location. The home was exactly as pictured. "

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

jen k.

[](https://www.expedia.ca/Peconic-Hotels-Newly-Renovated.h118737819.Hotel-Information)

![Sun loungers, beach towels](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698318/a339ae20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698318/w906h683x59y0-bf9a7a90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698318/723094cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698318/9eada5e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Pipes Cove

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

9.8/10

Exceptional

(31 reviews)

"Property management was great, responsive and helpful recommendations. The property was immaculate and perfectly located for everything from the beach to ferry, restaurants, Main Street and wineries. Plenty of parking on site. Kitchen was well stocked with everything to make a meal or to cook out. Wonderful place!"

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

Laurie G.

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

![Microwave](https://images.trvl-media.com/lodging/121000000/120190000/120181100/120181056/90548fa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120190000/120181100/120181056/fede96ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120190000/120181100/120181056/w3845h1809x0y27-8459e752.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120190000/120181100/120181056/d205216b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Southold

[](https://www.expedia.ca/Southold-Hotels-Surrounded-By-Nature.h120181056.Hotel-Information)

10/10

Exceptional

(3 reviews)

"We enjoyed our stay here. Great host, easy check in. Clean, comfortable and centrally located. Would definitely stay again. "

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

Cheryl H.

[](https://www.expedia.ca/Southold-Hotels-Surrounded-By-Nature.h120181056.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)

![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/9e0f05a8.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)

![Bar (on property)](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/0884fbbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Greenport

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

9.0/10

Wonderful

(4 reviews)

"We thoroughly enjoyed our stay!"

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

Parent From The Heart, Inc. E.

CA $163

CA $274 total

includes taxes & fees

Jan 28 - Jan 29

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73730000/73728900/73728881/115e86e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/74000000/73730000/73728900/73728881/3becc954.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/74000000/73730000/73728900/73728881/c8aa4b2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/74000000/73730000/73728900/73728881/3b9d18d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Mattituck

[](https://www.expedia.ca/Mattituck-Hotels-Modern-Cottage-In-Northfork-Steps-From-Love-Lane-And-Veterans-Beach.h73728881.Hotel-Information)

10/10

Exceptional

(39 reviews)

"Loved the house and the location. Walking distance to the beach and a few minutes from a bunch of vineyards. Would highly recommend this one to everyone!"

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

Daniel S.

[](https://www.expedia.ca/Mattituck-Hotels-Modern-Cottage-In-Northfork-Steps-From-Love-Lane-And-Veterans-Beach.h73728881.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/113000000/112710000/112700700/112700627/0f4016dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/113000000/112710000/112700700/112700627/6aa8f2cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/113000000/112710000/112700700/112700627/4e860fac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/113000000/112710000/112700700/112700627/a2ca3c30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Greenport

[](https://www.expedia.ca/Greenport-Hotels-Spacious-North-Fork-Home-In-Greenport.h112700627.Hotel-Information)

10/10

Exceptional

(4 reviews)

"Perfect location and accommodations for our family getaway. The kids loved the pool and the basketball hoop.Overall, the house was very comfortable and well equipped. "

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

Abby D.

[](https://www.expedia.ca/Greenport-Hotels-Spacious-North-Fork-Home-In-Greenport.h112700627.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/110000000/109920000/109916000/109915956/e981abed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/110000000/109920000/109916000/109915956/dcd0ddad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/110000000/109920000/109916000/109915956/9ba976db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109920000/109916000/109915956/w2476h1170x56y0-4f7d599f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Southold

[](https://www.expedia.ca/Southold-Hotels-Country-BEACH-Home.h109915956.Hotel-Information)

10/10

Exceptional

(1 review)

"Very comfortable and clean home! The hosts were very nice and helpful! Would definitely return!"

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

Megan & Chris D.

[](https://www.expedia.ca/Southold-Hotels-Country-BEACH-Home.h109915956.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/79000000/78600000/78591900/78591812/99f61ace.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/79000000/78600000/78591900/78591812/2092e42b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/79000000/78600000/78591900/78591812/3ed5393a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78600000/78591900/78591812/017f42a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Mattituck

[](https://www.expedia.ca/Laurel-Hotels-Mattiuck-Retreat.h78591812.Hotel-Information)

10/10

Exceptional

(16 reviews)

"Wonderful time. The backyard / pool was amazing. "

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

Kaitlynn W.

[](https://www.expedia.ca/Laurel-Hotels-Mattiuck-Retreat.h78591812.Hotel-Information)

![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/35000000/34450000/34445000/34444936/2c92b84f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34450000/34445000/34444936/25f20d33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/35000000/34450000/34445000/34444936/fadbeb81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sun loungers, beach towels](https://images.trvl-media.com/lodging/35000000/34450000/34445000/34444936/5de02ce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Southold

[](https://www.expedia.ca/Southold-Hotels-Waterfront.h34444936.Hotel-Information)

10/10

Exceptional

(19 reviews)

"Amazing from start to finish"

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

zadick a.

[](https://www.expedia.ca/Southold-Hotels-Waterfront.h34444936.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/105000000/104100000/104090300/104090249/dfb82f83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/105000000/104100000/104090300/104090249/c6e94345.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/105000000/104100000/104090300/104090249/0be10ccc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/105000000/104100000/104090300/104090249/c15ceaad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Laurel

[](https://www.expedia.ca/Laurel-Hotels-Bahia-Mar-Beach-House.h104090249.Hotel-Information)

10/10

Exceptional

(6 reviews)

"My favorite stay to date! Just perfection all around!"

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

kathleen y.

[](https://www.expedia.ca/Laurel-Hotels-Bahia-Mar-Beach-House.h104090249.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/113000000/112800000/112791900/112791823/95d612f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace, stereo](https://images.trvl-media.com/lodging/113000000/112800000/112791900/112791823/ed373c72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/113000000/112800000/112791900/112791823/0bce8e1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112800000/112791900/112791823/0f528c0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Mattituck

[](https://www.expedia.ca/Mattituck-Hotels-Mattituck-Luxury-Estate-Pool-5-Bedrooms.h112791823.Hotel-Information)

[](https://www.expedia.ca/Mattituck-Hotels-Mattituck-Luxury-Estate-Pool-5-Bedrooms.h112791823.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/57000000/56920000/56911800/56911757/3180c60a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/57000000/56920000/56911800/56911757/w2048h1536x0y0-1200d322.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/57000000/56920000/56911800/56911757/09c2d265.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/57000000/56920000/56911800/56911757/3e6315fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Southold

[](https://www.expedia.ca/Southold-Hotels-Heated-Pool-On-Goose-Creek.h56911757.Hotel-Information)

9.6/10

Exceptional

(24 reviews)

"Beautiful property that exceeded expectations. Pros: lovely heated pool, spacious deck, all modern and clean, tastefully decorated, home office if you need to do a bit of work, completely equipped kitchen, comfortable beds, fast wi-fi, powerful & quiet central A/C, located on a quiet street but still 2 miles from excellent dining in Southold, enclosed backyard which is private and beautifully landscaped. A gem!"

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

Mark D.

[](https://www.expedia.ca/Southold-Hotels-Heated-Pool-On-Goose-Creek.h56911757.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/92000000/91430000/91429300/91429257/533133f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/92000000/91430000/91429300/91429257/eb764313.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/92000000/91430000/91429300/91429257/cac6b222.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/92000000/91430000/91429300/91429257/67d9cd49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Mattituck

[](https://www.expedia.ca/Mattituck-Hotels-Beach-House-Cape-In-North-Forks-Wine-Country.h91429257.Hotel-Information)

10/10

Exceptional

(2 reviews)

"House was beautiful as was the giant pool Backyard was like a sanctuary with bird feeders and beautiful maintained landscaping. Home was well stocked and beautifully maintained. "

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

Kathy L.

[](https://www.expedia.ca/Mattituck-Hotels-Beach-House-Cape-In-North-Forks-Wine-Country.h91429257.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/0fd41d32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/94f208d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/e5db1f36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/5f36ce70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Southold

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

10/10

Exceptional

(3 reviews)

"good experience"

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

Anonymous traveller

CA $822

CA $1,609 total

includes taxes & fees

Jan 29 - Jan 30

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

![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108600000/108598500/108598430/daa9d409.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108600000/108598500/108598430/a749c4ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sun loungers, beach towels](https://images.trvl-media.com/lodging/109000000/108600000/108598500/108598430/9fe6908a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/109000000/108600000/108598500/108598430/3f7c1e97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Southold

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

10/10

Exceptional

(8 reviews)

"We loved everything about this home. It is well appointed, clean and comfy. The outdoor seating space is also wonderful, as is the nearby beach. I highly recommend this perfect vacation spot. "

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

Regine B.

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/82000000/81230000/81224400/81224369/w1284h855x0y0-ba1c12d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/82000000/81230000/81224400/81224369/w1284h855x0y3-5934a78a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/82000000/81230000/81224400/81224369/w1284h846x0y0-b3d7f28a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/82000000/81230000/81224400/81224369/w1284h852x0y0-15000c8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Greenport

[](https://www.expedia.ca/Greenport-Hotels-Beautifully-Renovated-2-Bedroom.h81224369.Hotel-Information)

10/10

Exceptional

(26 reviews)

"A convenient location in Greenport - walkable to town - worked perfectly for us and friends while in for a family wedding. "

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

Melissa S.

[](https://www.expedia.ca/Greenport-Hotels-Beautifully-Renovated-2-Bedroom.h81224369.Hotel-Information)

![Smart TV, fireplace, stereo, offices](https://images.trvl-media.com/lodging/117000000/116470000/116469500/116469401/ab7949bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116470000/116469500/116469401/2b86a000.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, stereo, offices](https://images.trvl-media.com/lodging/117000000/116470000/116469500/116469401/ed7f8615.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, stereo, offices](https://images.trvl-media.com/lodging/117000000/116470000/116469500/116469401/1c4bad92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Cutchogue

[](https://www.expedia.ca/Cutchogue-Hotels-Elevated-North-Fork-Escape-With-Chic-Interiors-And-Private-Poolside-Oasis.h116469401.Hotel-Information)

[](https://www.expedia.ca/Cutchogue-Hotels-Elevated-North-Fork-Escape-With-Chic-Interiors-And-Private-Poolside-Oasis.h116469401.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/34000000/33660000/33656400/33656388/1e8b1bfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/34000000/33660000/33656400/33656388/2d67ccff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![6 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33660000/33656400/33656388/65fe9041.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/34000000/33660000/33656400/33656388/963412f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Greenport

[](https://www.expedia.ca/Greenport-Hotels-NOFO-ESCAPE-Relax-Swim-Enjoy-Bachelorettes-Weddings-Family-Vacation.h33656388.Hotel-Information)

9.8/10

Exceptional

(31 reviews)

"Very kind, accommodating host with a gorgeous property"

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

Zachary H.

[](https://www.expedia.ca/Greenport-Hotels-NOFO-ESCAPE-Relax-Swim-Enjoy-Bachelorettes-Weddings-Family-Vacation.h33656388.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007808/33e4d133.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007808/993861ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007808/5bedca6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, beach towels](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007808/2407cade.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Mattituck

[](https://www.expedia.ca/Mattituck-Hotels-Beach.h34007808.Hotel-Information)

10/10

Exceptional

(78 reviews)

"This stay was perfect for a small group weekend trip. We stayed for a wedding and it was an awesome home base."

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

Katie B.

[](https://www.expedia.ca/Mattituck-Hotels-Beach.h34007808.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=2026-02-07&endDate=2026-02-08&regionId=553248635976002319&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

[](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=2026-04-24&d1=2026-04-24&endDate=2026-04-27&d2=2026-04-27&lodging=APART_HOTEL)

Private vacation homes

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Apartments

[](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=2026-04-24&d1=2026-04-24&endDate=2026-04-27&d2=2026-04-27&lodging=APARTMENT)

Condos

[](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=2026-04-24&d1=2026-04-24&endDate=2026-04-27&d2=2026-04-27&lodging=CONDO)

Villas

[](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=2026-04-24&d1=2026-04-24&endDate=2026-04-27&d2=2026-04-27&lodging=VILLA)

Cottages

[](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=2026-04-24&d1=2026-04-24&endDate=2026-04-27&d2=2026-04-27&lodging=COTTAGE)

Cabins

[](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=2026-04-24&d1=2026-04-24&endDate=2026-04-27&d2=2026-04-27&lodging=CABIN)

Houseboats

[](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=2026-04-24&d1=2026-04-24&endDate=2026-04-27&d2=2026-04-27&lodging=HOUSE_BOAT)

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## Top Town of Southold Town Hotel Reviews

![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

"Room was great. Clean and comfortable. Glad I found this place and will be back. "

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

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

### Vine & Sand

10/10 Excellent

"Wonderful stay"

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

"The staff was wonderful and the room and views fantastic."

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

"This hosts properties are so thoughtfully stocked, ,i felt home only nicer! Cabana is a real treat. Beautiful, new, clean, beautifully done. Every need of staying away in a home is thought of. Great area in walking distance to town as well. Host is always available for quick communications.well. "

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

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

### Sound View Greenport

10/10 Excellent

"Amazing room and view from the room was perfect! "

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

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

### The Menhaden

10/10 Excellent

"Loved our stay at the Menhaden! Everything was great especially the staff who went beyond our expectations...from offering us champagne and my husband a great mocktail to cleaning the snow off our car! The place is so pretty and the bar has all fun games & all albums you can play. The king room was large, no bath though :( and it was a bit cold in there, they did try and fix it though. Breakfast and goodies available all day on our floor with sodas, water, coffee and cappuccinos :). "

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

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

### Zey Hotel

10/10 Excellent

"Quiet yet situated right in the heart of Greenport."

[](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

"Terrific service, clean, excellent location. "

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

![Modern Farmhouse Steps to Beach and Love Lane ](https://images.trvl-media.com/lodging/74000000/73730000/73728900/73728881/22b35fec_y.jpg)

### Modern Farmhouse Steps to Beach and Love Lane 

10/10 Excellent

"The host was great and got in touch with us quickly. The cottage and amenities were just as described! We had a wonderful visit!"

[](https://expedia.ca/Mattituck-Hotels-Modern-Cottage-In-Northfork-Steps-From-Love-Lane-And-Veterans-Beach.h73728881.Hotel-Information)

## Find out more about Town of Southold Town

## Town of Southold Town Vacation Homes information

| Number of reviews | 305                |
| ----------------- | ------------------ |
| Accommodation     | 213 Vacation Homes |
| Lowest Price      | CA $274            |
| Highest Price     | CA $1,609          |

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- [Villas in Peconic ](https://www.expedia.ca/Peconic-Villas.d144477-aaVillas.Travel-Guide-Accommodation)
- [Hotels near Pindar Vineyards ](https://www.expedia.ca/Pindar-Vineyards-Hotels.0-l6326965-0.Travel-Guide-Filter-Hotels)
- [B&B in Shelter Island ](https://www.expedia.ca/Shelter-Island-Bed-And-Breakfast.d157359-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [B&B in Shelter Island Heights ](https://www.expedia.ca/Shelter-Island-Heights-Bed-And-Breakfast.d183716-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Beach Hotel Hotels in Shelter Island Heights ](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Beach-Hotel.0-0-d183716-tBeachHotel.Travel-Guide-Filter-Hotels)
- [Boutique Hotels in Shelter Island Heights ](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Boutique-Hotel.0-0-d183716-tBoutiqueHotel.Travel-Guide-Filter-Hotels)
- [Hotels & Resorts for Couples in Shelter Island Heights ](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Couples-Resorts-Hotels.0-0-d183716-tCouplesResortsHotels.Travel-Guide-Filter-Hotels)
- [Pet-Friendly Hotels in Shelter Island Heights ](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Pet-Friendly-Hotel.0-0-d183716-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [Spa Hotels in Shelter Island Heights ](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Spa-Hotel.0-0-d183716-tSpaHotel.Travel-Guide-Filter-Hotels)
- [Shelter Island Heights Hotels ](https://www.expedia.ca/Shelter-Island-Heights-Hotels.d183716.Travel-Guide-Hotels)
- [Resorts in Shelter Island Heights ](https://www.expedia.ca/Shelter-Island-Heights-Resort-Hotels.d183716-aaResortHotels.Travel-Guide-Accommodation)
- [Adults Only Resorts & in Shelter Island ](https://www.expedia.ca/Shelter-Island-Hotels-Adults-Only-Resorts.0-0-d157359-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels)
- [Beach Hotel Hotels in Shelter Island ](https://www.expedia.ca/Shelter-Island-Hotels-Beach-Hotel.0-0-d157359-tBeachHotel.Travel-Guide-Filter-Hotels)
- [Boutique Hotels in Shelter Island ](https://www.expedia.ca/Shelter-Island-Hotels-Boutique-Hotel.0-0-d157359-tBoutiqueHotel.Travel-Guide-Filter-Hotels)
- [Cheap Hotels in Shelter Island ](https://www.expedia.ca/Shelter-Island-Hotels-Cheap-Hotels.0-0-d157359-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Hotels & Resorts for Couples in Shelter Island ](https://www.expedia.ca/Shelter-Island-Hotels-Couples-Resorts-Hotels.0-0-d157359-tCouplesResortsHotels.Travel-Guide-Filter-Hotels)
- [Family Hotels in Shelter Island ](https://www.expedia.ca/Shelter-Island-Hotels-Family-Hotel.0-0-d157359-tFamilyHotel.Travel-Guide-Filter-Hotels)
- [Hotels with a Pool in Shelter Island ](https://www.expedia.ca/Shelter-Island-Hotels-Hotel-With-Pool.0-0-d157359-tHotelwithPool.Travel-Guide-Filter-Hotels)
- [Hotels with Free Breakfast in Shelter Island ](https://www.expedia.ca/Shelter-Island-Hotels-Hotels-With-Free-Breakfast.0-0-d157359-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in Shelter Island ](https://www.expedia.ca/Shelter-Island-Hotels-Luxury-Hotel.0-0-d157359-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Oceanfront Hotels in Shelter Island ](https://www.expedia.ca/Shelter-Island-Hotels-Oceanfront-Hotels.0-0-d157359-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Shopping Hotels in Shelter Island ](https://www.expedia.ca/Shelter-Island-Hotels-Shopping-Hotel.0-0-d157359-tShoppingHotel.Travel-Guide-Filter-Hotels)
- [Shelter Island Hotels ](https://www.expedia.ca/Shelter-Island-Hotels.d157359.Travel-Guide-Hotels)
- [Houseboats in Shelter Island ](https://www.expedia.ca/Shelter-Island-Houseboats.d157359-aaHouseboats.Travel-Guide-Accommodation)
- [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)
- [Cheap Hotels in Southold ](https://www.expedia.ca/Southold-Hotels-Cheap-Hotels.0-0-d183719-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Romantic Hotels in Southold ](https://www.expedia.ca/Southold-Hotels-Romantic-Hotel.0-0-d183719-tRomanticHotel.Travel-Guide-Filter-Hotels)
- [Southold Hotels ](https://www.expedia.ca/Southold-Hotels.d183719.Travel-Guide-Hotels)
- [Motels in Southold ](https://www.expedia.ca/Southold-Motels.d183719-aaMotels.Travel-Guide-Accommodation)
- [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 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)