Title: Southold Villas from CA $102 | Expedia.ca

[Hotels in Southold](https://expedia.ca/Southold-Hotels.d183719.Travel-Guide-Hotels)[Vacation Rentals in Southold](https://expedia.ca/Southold-Vacation-Rentals.d183719.Travel-Guide-VacationRentals)[Flights to Southold](https://expedia.ca/Cheap-Flights-To-Southold.d183719.Travel-Guide-Flights)[Southold Car Rentals](https://expedia.ca/Car-Rentals-In-Southold.d183719.Car-Rental-Guide)[Southold Vacation Packages](https://expedia.ca/Southold.d183719.Destination-Travel-Guides)

![Day trip to North Fork wineries. Stopped at this beach for a break before driving back to the city. #sunset #nature #wanderlust #waterlust #beach #colorful #citylife #NikonD7100 #Manfratto tripod. ](https://images.trvl-media.com/place/183719/81468873-e891-4a92-aa0d-1938572ea198.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Benny Goh 

![](https://images.trvl-media.com/place/183719/81468873-e891-4a92-aa0d-1938572ea198.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=183719&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 two months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

No exact matches found, but these alternatives could be just right

## Recommended hotels in Southold

![Restaurant](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/7f5c2322.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)

![Front of property](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/90ac61e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/5a27472c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Shoals Suites and Slips

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

Southold

9.4/10

Exceptional

(243 reviews)

"Great stay, will definitely go again"

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

ANTONIO J

CA $215

CA $280 total

includes taxes & fees

Apr 2 - Apr 3

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

![Exterior](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/5d25c168.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/242d28e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior detail](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/bb62973a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach nearby, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/e94ab56a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vine & Sand

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

Southold

9.6/10

Exceptional

(15 reviews)

"Wonderful stay"

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

Judy

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

![Exterior](https://images.trvl-media.com/lodging/97000000/96090000/96087300/96087261/w910h683x58y0-b0ea2d96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96090000/96087300/96087261/6043715a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace, books](https://images.trvl-media.com/lodging/97000000/96090000/96087300/96087261/w1024h680x0y0-e5b26f05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/97000000/96090000/96087300/96087261/359c88e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower

[](https://www.expedia.ca/Southold-Hotels-Room-4-Queen-Bed-And-Adjacent-Bathroom-With-Rain-Shower.h96087261.Hotel-Information)

Southold

CA $428

CA $556 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Southold-Hotels-Room-4-Queen-Bed-And-Adjacent-Bathroom-With-Rain-Shower.h96087261.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/97000000/96090000/96086700/96086691/w910h683x58y0-4b2ff646.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace, books](https://images.trvl-media.com/lodging/97000000/96090000/96086700/96086691/w1024h680x0y0-07461725.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96090000/96086700/96086691/w450h683x287y0-3203696c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96090000/96086700/96086691/w1022h681x0y0-bb3c91cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub

[](https://www.expedia.ca/Southold-Hotels-Room-1-King-Bed-And-Ensuite-Bathroom-With-Soaking-Tub.h96086691.Hotel-Information)

Southold

10/10

Exceptional

(1 review)

"Must like historical houses and little sausage-shaped dogs. A seamless blend of old and mod. Room is meticulously shiny clean. Substantial bedding designed for a good night’s sleep. High-end details (furnishings, footed tub with heat lamp and fluffy robes), culture (gallery), included breakfast is simple perfection due to high-quality ingredients/sourcing (fresh pastries, eggs, butter, fruit). Pool and hot tub divine. Our hosts are upbeat and fun and really went beyond for us. There are great...

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

Jessica P.

CA $471

CA $613 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Southold-Hotels-Room-1-King-Bed-And-Ensuite-Bathroom-With-Soaking-Tub.h96086691.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/97000000/96050000/96043300/96043294/w910h683x58y0-5ae7bf4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace, books](https://images.trvl-media.com/lodging/97000000/96050000/96043300/96043294/w1024h680x0y0-30a975e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96050000/96043300/96043294/f5c4e2e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/97000000/96050000/96043300/96043294/43746f0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower

[](https://www.expedia.ca/Southold-Hotels-Room-3-Queen-Bed-And-Ensuite-Bathroom-With-Rain-Shower.h96043294.Hotel-Information)

Southold

10/10

Exceptional

(1 review)

"Great experience. Wonderful hosts. "

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

Mark L.

CA $428

CA $556 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Southold-Hotels-Room-3-Queen-Bed-And-Ensuite-Bathroom-With-Rain-Shower.h96043294.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/97000000/96090000/96087100/96087076/w910h683x58y0-54a2309a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace, books](https://images.trvl-media.com/lodging/97000000/96090000/96087100/96087076/w1024h680x0y0-ae057e3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96090000/96087100/96087076/1fbd9077.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/97000000/96090000/96087100/96087076/e4b38241.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower

[](https://www.expedia.ca/Southold-Hotels-Room-2-King-Bed-And-Ensuite-Bathroom-With-Rain-Shower.h96087076.Hotel-Information)

Southold

CA $471

CA $613 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Southold-Hotels-Room-2-King-Bed-And-Ensuite-Bathroom-With-Rain-Shower.h96087076.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/735ceae9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/174f7a84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/dc9b088b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Combined shower/tub, hair dryer, towels, soap](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/afd83ae8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spark by Hilton Guilford

[](https://www.expedia.ca/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.Hotel-Information)

Guilford

8.8/10

Excellent

(101 reviews)

"The front desk staff were excellent, clean and comfortable stay."

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

JUstine

CA $148

CA $170 total

includes taxes & fees

Apr 1 - Apr 2

[](https://www.expedia.ca/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/92c1b984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/f2520f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free cribs/infant beds, rollaway beds, free WiFi, bed sheets](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/d1788901.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free cribs/infant beds, rollaway beds, free WiFi, bed sheets](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/f9bec315.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Clinton Motel

[](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.Hotel-Information)

Clinton

8.6/10

Excellent

(302 reviews)

"The room was comfortable and clean. A good value for the money."

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

Michael

CA $106

CA $122 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/e3411bfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Studio, Private Bathroom (King Size Bed)](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/65285c66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Suite, 2 Double Beds, Non Smoking, Kitchenette](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/a4c86ff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Suite, Private Bathroom | Private kitchen](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/733470c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Niantic Inn

[](https://www.expedia.ca/Niantic-Hotels-The-Niantic-Inn.h15001889.Hotel-Information)

Niantic

9.2/10

Wonderful

(141 reviews)

"Quiet and warm and clean. Nice touch from Housekeeping too! "

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

Jessica

CA $157

CA $181 total

includes taxes & fees

Mar 16 - Mar 17

[](https://www.expedia.ca/Niantic-Hotels-The-Niantic-Inn.h15001889.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/106000000/105360000/105355600/105355576/5ba709f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/106000000/105360000/105355600/105355576/a5732811.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/106000000/105360000/105355600/105355576/49ec459f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/106000000/105360000/105355600/105355576/88e93fea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beach Cottage, private beach and pass

[](https://www.expedia.ca/Niantic-Hotels-Quaint-Beach-Cottage.h105355576.Hotel-Information)

East Lyme

10/10

Exceptional

(9 reviews)

"It was PERFECT way to spend USCGA Parent’s Weekend!!"

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

Kerri G.

CA $232

CA $544 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Niantic-Hotels-Quaint-Beach-Cottage.h105355576.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/77ded06a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/7d66373d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/2ca462c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, coffee/tea maker, cookware/dishes/utensils, spices](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/30204b81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Stern at Soundview · Beach+Ocean+Sunrise

[](https://www.expedia.ca/Old-Lyme-Hotels-The-Stern-At-Soundview-BeachOceanViewSunrise.h106147914.Hotel-Information)

Old Lyme

10/10

Exceptional

(3 reviews)

"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "

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

Lylian

CA $135

CA $301 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Old-Lyme-Hotels-The-Stern-At-Soundview-BeachOceanViewSunrise.h106147914.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1400000/1400000/1399998/7368827e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, coffee/tea maker](https://images.trvl-media.com/lodging/2000000/1400000/1400000/1399998/42c9a535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/2000000/1400000/1400000/1399998/7fef8cbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1400000/1400000/1399998/cab0b22b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tower Inn And Suites Of Guilford - Madison

[](https://www.expedia.ca/New-Haven-Hotels-Tower-Inn-And-Suites-Of-Guilford-Madison.h1399998.Hotel-Information)

Guilford

7.4/10

Good

(238 reviews)

"I really enjoy staying here. The family who runs this motel are so nice. I used to live in Guilford and moved out of state. I return to Conn frequently and always stay here. "

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

Susan B

CA $122

CA $140 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/New-Haven-Hotels-Tower-Inn-And-Suites-Of-Guilford-Madison.h1399998.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/65eed284.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/2e009ba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/8e3d5f6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/0c11d8f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1-bedroom cottage with Grove Beach 🏖️ access.

[](https://www.expedia.ca/Clinton-Hotels-1-Bedroom-Cottage-With-Grove-Beach-Access.h90991445.Hotel-Information)

Clinton

9.6/10

Exceptional

(37 reviews)

"Many local restaurants near by. Christy's for breakfast was very good. "

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

Benjamin H.

CA $109

CA $245 total

includes taxes & fees

Mar 6 - Mar 7

[](https://www.expedia.ca/Clinton-Hotels-1-Bedroom-Cottage-With-Grove-Beach-Access.h90991445.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/f5b274b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/8ffa2c0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/be26a516.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn Old Saybrook - Westbrook

[](https://www.expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information)

Old Saybrook

7.8/10

Good

(1,002 reviews)

"Hotel was very clean, staff was wonderful and the pool was so relaxing. It was a quick visit but definitely would stay again if I was in that area. "

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

Kathleen

CA $138

CA $159 total

includes taxes & fees

Mar 9 - Mar 10

[](https://www.expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71990000/71987700/71987631/2455988a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/72000000/71990000/71987700/71987631/b6fd2c06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, internet](https://images.trvl-media.com/lodging/72000000/71990000/71987700/71987631/33cb5945.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/72000000/71990000/71987700/71987631/44a547d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aqua by American Beech - Superior King

[](https://www.expedia.ca/Riverhead-Hotels-Aqua-By-American-Beech-Superior-King.h71987631.Hotel-Information)

Aquebogue

10/10

Exceptional

(5 reviews)

"Had the best stay! Will be back "

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

Jennifer

CA $162

CA $273 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Riverhead-Hotels-Aqua-By-American-Beech-Superior-King.h71987631.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/afdef753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/5cb2e3e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/31bd2f7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/72f65e39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pier Blue Inn Old Saybrook - Essex

[](https://www.expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information)

Saybrook Manor

8.0/10

Very good

(1,001 reviews)

"Room was clean and warm and the staff was very friendly "

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

Pattie

[](https://www.expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/147e40ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast area](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/ee8b7737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/f90ba663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/cfee764e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Shorewood Inn

[](https://www.expedia.ca/Riverhead-Hotels-Shorewood-Inn.h15241380.Hotel-Information)

Riverhead

8.4/10

Very good

(724 reviews)

"ROOM WAS CLEAN, WARM, GOOD PARKING"

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

JOSEPH

CA $125

CA $143 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Riverhead-Hotels-Shorewood-Inn.h15241380.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71990000/71987700/71987644/09001f14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/72000000/71990000/71987700/71987644/711fd693.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/72000000/71990000/71987700/71987644/5f9ae7a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/72000000/71990000/71987700/71987644/f940658a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aqua by American Beech - Rooftop Suite

[](https://www.expedia.ca/Riverhead-Hotels-Aqua-By-American-Beech-Rooftop-Suite.h71987644.Hotel-Information)

Aquebogue

10/10

Exceptional

(1 review)

"Quick stay after a day at the wineries. Location is is set in a beautiful quiet area and the view is just amazing. The staff could truly not be any better, any request or issue was dealt with in literally a minute. Room was perfect, clean and made you feel at home with anything you needed. Will definitely be back!"

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

Jerrold H.

CA $271

CA $416 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Riverhead-Hotels-Aqua-By-American-Beech-Rooftop-Suite.h71987644.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/15000000/14710000/14708600/14708579/32a9a3ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 1 King Bed](https://images.trvl-media.com/lodging/15000000/14710000/14708600/14708579/2e44d319.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double Room, 2 Double Beds](https://images.trvl-media.com/lodging/15000000/14710000/14708600/14708579/08314c4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/15000000/14710000/14708600/14708579/4dcdf083.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lamplighter Motel - Clinton, Connecticut

[](https://www.expedia.ca/Old-Saybrook-Hotels-Lamplighter-Motel-Clinton.h14708579.Hotel-Information)

Clinton

6.4/10

(229 reviews)

"Would stay again. "

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

pamela

CA $89

CA $102 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Old-Saybrook-Hotels-Lamplighter-Motel-Clinton.h14708579.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/19000000/18520000/18516100/18516036/09f33f29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/19000000/18520000/18516100/18516036/039bea88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18520000/18516100/18516036/2ffae8cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/19000000/18520000/18516100/18516036/b5361d70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Residence Inn by Marriott New York Long Island East End

[](https://www.expedia.ca/Riverhead-Hotels-Residence-Inn-By-Marriott-New-York-Long-Island-East-End.h18516036.Hotel-Information)

Riverhead

9.0/10

Wonderful

(1,002 reviews)

"great place,I loved it"

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

Ryan

CA $161

CA $184 total

includes taxes & fees

Mar 5 - Mar 6

[](https://www.expedia.ca/Riverhead-Hotels-Residence-Inn-By-Marriott-New-York-Long-Island-East-End.h18516036.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=2026-03-16&endDate=2026-03-17&regionId=183719&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Find vacation rentals that suit your style

Cottages

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Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America&regionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=VACATION_HOME)

Apartments

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Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America&regionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=APART_HOTEL)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America&regionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=VILLA)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America&regionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=CONDO)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America&regionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=HOUSE_BOAT)

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## Top Southold Hotel Reviews

![Saybrook Point Resort & Marina](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108_y.jpg)

### Saybrook Point Resort & Marina

10/10 Excellent

"Great room clean and comfortable."

[](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information)

![Hotel Indigo East End by IHG](https://images.trvl-media.com/lodging/4000000/3480000/3475700/3475618/75016698_y.jpg)

### Hotel Indigo East End by IHG

10/10 Excellent

"Friendly"

[](https://expedia.ca/Riverhead-Hotels-Hotel-Indigo-East-End.h3475618.Hotel-Information)

![Quality Inn Old Saybrook - Westbrook](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg)

### Quality Inn Old Saybrook - Westbrook

10/10 Excellent

"I frequent this hotel on a regular basis during the winter time as its within walking distance to my job. The staff is always friendly. The rooms are spotless and the General Manager Joe is always very accomodating. I recommend this hotel to anyone staying in the area and looking for a very clean hotel with super friendly staff. "

[](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information)

![The Sagaponack](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/d64f35e8_y.jpg)

### The Sagaponack

10/10 Excellent

"Enjoyed our stay. Clean room , temperature in room was cozy, bed was comfortable and snack bar in main house was a nice touch."

[](https://expedia.ca/Wainscott-Hotels-The-Wainscott-Inn.h81143153.Hotel-Information)

![The Bentley Hotel Southampton](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98_y.jpg)

### The Bentley Hotel Southampton

10/10 Excellent

"Nice "

[](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information)

![Residence Inn by Marriott New York Long Island East End](https://images.trvl-media.com/lodging/19000000/18520000/18516100/18516036/b5361d70_y.jpg)

### Residence Inn by Marriott New York Long Island East End

10/10 Excellent

"Perfect "

[](https://expedia.ca/Riverhead-Hotels-Residence-Inn-By-Marriott-New-York-Long-Island-East-End.h18516036.Hotel-Information)

![The Preston House & Hotel](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/1f765cec_y.jpg)

### The Preston House & Hotel

10/10 Excellent

"10/10"

[](https://expedia.ca/Riverhead-Hotels-The-Preston-House-Hotel.h21825843.Hotel-Information)

![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg)

### Water's Edge Resort & Spa

10/10 Excellent

"The staff throughout our stay was amazing. Our room was spotless and so comfortable. Beautiful view from the balcony. The spa was beautiful. We had relaxing massages. We ate in the main dining room. Our waiter was great and the food was amazing. We had so much fun using the jacuzzi and the pool which were very clean. So convenient having Starbucks in the hotel and a lovely gift shop. The valet staff were kind and helpful with our luggage. We will definitely stay here again and recommend this hotel for your stay. We went during the cold weather but would love to come back in the warmer weather."

[](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information)

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

### Sound View Greenport

10/10 Excellent

"The hotel was exceptional! We love staying at soundview during the winter months! "

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

## Find out more about Southold

## Southold Villas information

| Number of reviews | 5,018     |
| ----------------- | --------- |
| Accommodation     | 35 Villas |
| Lowest Price      | CA $102   |
| Highest Price     | CA $613   |

## Frequently asked questions

### Why book your villa in Southold with Expedia?

### How can I find cheap villas in Southold?

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- [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)
- [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)
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- [Flights from Shelter Island ](https://www.expedia.ca/lp/flights/157359/flights-from-shelter-island)
- [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)
- [Kontokosta Winery ](https://www.expedia.ca/Kontokosta-Winery-Greenport.d6326928.Vacation-Attraction)
- [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)

- [Book Villas in Southold on Expedia.com ](https://www.expedia.com/Southold-Villas.d183719-aaVillas.Travel-Guide-Accommodation)