Title: Southold Vacation Home Rentals from CA $358: Search Top Private Vacation Homes for Rent | Expedia.ca

  

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# Southold Vacation Rentals

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## Check prices for these dates

Next weekend

[Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-11-14&endDate=2025-11-16&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Southold Vacation Homes

![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/10ef3e76.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)

![Dining](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/5f36ce70.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)

### Beautifully farmhouse

Southold

10/10

Exceptional

(3)

"good experience"

CA $843

CA $1,629 total

includes taxes & fees

Oct 20 - Oct 21

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

![Property grounds](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/f7b0c3cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/0c0a866f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/669e9fe2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/8aa6190f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Rogers Lake House (87) · CT College+Beach+USCGA

Old Lyme

10/10

Exceptional

(2)

"My family and I came for an 8 day event from a different state and wanted a clean and comfortable place to stay with our at the time 9 month old daughter. And this place did exactly that. Comfortable and CLEAN. The owner did a great job with details. Even when we had unexpected check out delays the owner showed human empathy. Great place!"

CA $121

CA $563 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Old-Lyme-Hotels-Rogers-Lake-House.h105301933.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/53000000/52070000/52069800/52069712/53aab435.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/53000000/52070000/52069800/52069712/f9f66e71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/53000000/52070000/52069800/52069712/fbefb98b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/53000000/52070000/52069800/52069712/6fccc75f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Insta-worthy Couples Retreat: Perfect for romantic getaway!

Old Lyme

9.6/10

Exceptional

(52)

"Great stay, charming cottage, hope to return"

CA $140

CA $358 total

includes taxes & fees

Oct 29 - Oct 30

[](https://www.expedia.ca/Mystic-New-London-Hotels-Seaside-Beach-Bungalow-At-Hawks-Nest.h52069712.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/4ecca3ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/809e0319.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/a53b6f84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/864047ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy quiet gem, private & fenced in backyard

East Hampton

9.4/10

Exceptional

(3)

"good times"

CA $139

CA $1,274 total

includes taxes & fees

Oct 21 - Oct 22

[](https://www.expedia.ca/East-Hampton-Hotels-Fall-In-Love-In-East-Hampton.h71000754.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/891accf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/1c400db4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/9036247c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/a0e54ecb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beachside Bliss w/ Game Room, Gym & Golf Green

Westbrook

CA $165

CA $676 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Westbrook-Hotels-Beachside-Bliss-W-Game-Room.h121396426.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/47172b27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/3f78326f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/02ffbf91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/1483cc0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private completely fenced in property. Near beach

Hampon Bays

9.6/10

Exceptional

(22)

"The house was very spacious and beautiful! The pool and patio were the major highlights. Pool was crystal clear and clean. We enjoyed our stay so much and hope to be back. Owner was very responsive with our questions "

CA $218

CA $1,864 total

includes taxes & fees

Oct 21 - Oct 22

[](https://www.expedia.ca/Hampton-Bays-Hotels-Private-Completely-Fenced-In-Property-Near-Beach.h66472313.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/b3f1fe2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/441cf856.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/3368cbed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/cee0fa4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### BRAND NEW 7BR7BA Southampton Estate - Heated Salt Pool, Mins to Beach & Town

Water Mill

10/10

Exceptional

(6)

"Highly recommend everything from start to finish went smoothly and it was a great experience!!"

CA $4,213

CA $8,168 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Water-Mill-Hotels-Ultimate-Water-Mill-Southampton-Escape-Stunning-7BR-Estate-For-Family-Friends.h78740383.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/106000000/105960000/105954000/105953994/c1c14546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105960000/105954000/105953994/200490ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/106000000/105960000/105954000/105953994/9a2f74fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105960000/105954000/105953994/b0e8e3c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Bridgehampton

9.6/10

Exceptional

(15)

"We had a one-night stay at this location. It was perfect for us from many perspectives and we enjoyed staying there. Very nice place!Thanks! "

CA $222

CA $538 total

includes taxes & fees

Oct 27 - Oct 28

[](https://www.expedia.ca/Bridgehampton-Hotels-Cozy-Bungalow-Available-Nearby-Bridgehampton-And-Sag-Harbor.h105953994.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/f8cef332.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h953x0y0-69414cc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/a2326e66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h960x0y0-cce9554c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

Saybrook Manor

9.6/10

Exceptional

(133)

"Great older house with everything you need to have a great time. Family event with 6 adults and 2 dogs enjoyed the house, the yard, and the area. Strongly recommend."

CA $421

CA $817 total

includes taxes & fees

Oct 20 - Oct 21

[](https://www.expedia.ca/Old-Saybrook-Hotels-Capt-Nathaniel-Clarke-Historic-Homestead.h18762073.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)

![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)

![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)

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

Greenport

9.0/10

Wonderful

(4)

"Great job "

CA $279

CA $427 total

includes taxes & fees

Oct 20 - Oct 21

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

![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/f20bc122.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/8ea39820.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/00b024ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/8791fbfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private beach on a fenced in property sunset views

Hampton Bays

10/10

Exceptional

(12)

"We liked our stay there. Clean house, beautiful sunset as described. Close to the beach. Very nice stay."

CA $499

CA $2,136 total

includes taxes & fees

Oct 21 - Oct 22

[](https://www.expedia.ca/Hampton-Bays-Hotels-Unique-Location-Fenced-In-Private-Beach.h92502496.Hotel-Information)

![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113440000/113439500/113439409/7a209baf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/114000000/113440000/113439500/113439409/8f1986e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113440000/113439500/113439409/d26d882e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/114000000/113440000/113439500/113439409/f8c8a8d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sag Harbor Water View w Dock 1.5ml from town

Bay Point

CA $6,319

CA $8,978 total

includes taxes & fees

Oct 18 - Oct 19

[](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Water-View-W-Dock.h113439409.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/35000000/34010000/34005300/34005296/w1163h764x0y0-2c7bc0ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34010000/34005300/34005296/cfaa160d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![6 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/35000000/34010000/34005300/34005296/36030f26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, foosball](https://images.trvl-media.com/lodging/35000000/34010000/34005300/34005296/f488ddfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches

Water Mill

10/10

Exceptional

(45)

"Catherine was a great homeowner and made sure everything was organized prior to our arrival. She was very kind and easy to communicate with. She also was able to make sure we could have an early check in. "

CA $2,734

CA $4,805 total

includes taxes & fees

Oct 27 - Oct 28

[](https://www.expedia.ca/Water-Mill-Hotels-6-Bedroom-Bridgehampton-Estate.h34005296.Hotel-Information)

![Oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/109000000/108020000/108011000/108010988/w1133h742x19y0-50746f6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/109000000/108020000/108011000/108010988/w1169h768x0y0-20f93b3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/109000000/108020000/108011000/108010988/w1109h758x16y4-b628a6e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108020000/108011000/108010988/w1133h693x19y0-54cefabf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Calverton

8.4/10

Very good

(7)

"prefect experience! The house is clean and well decorated with a large organized yard. Many parking spaces. "

CA $701

CA $1,268 total

includes taxes & fees

Oct 22 - Oct 23

[](https://www.expedia.ca/Calverton-Hotels-Spacious-5-Bedroom-House-In-Enchanting-Calverton-With-WiFi.h108010988.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/bb644073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/6a96971c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/ee30d2e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/4bd3774d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Northfork Townhouse- walk to all/ newly renovated

Greenport

9.6/10

Exceptional

(9)

"The place was as advertised and in great walking distance to everything in town! "

CA $639

CA $1,165 total

includes taxes & fees

Oct 19 - Oct 20

[](https://www.expedia.ca/Greenport-Hotels-Greenport-Village-Townhouse.h74196767.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/f6c15885.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/aeb85212.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/126bef9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/b7d556ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 5-bedroom house with water views and 2 houses from the bay.

Sag Harbor

CA $5,617

CA $9,039 total

includes taxes & fees

Oct 21 - Oct 22

[](https://www.expedia.ca/Sag-Harbor-Hotels-Spacious-5-Bedroom-House-With-Water-Views-And-2-Houses-From-The-Bay.h113530184.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74210000/74202200/74202120/w1035h701x17y0-8bcaee6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/75000000/74210000/74202200/74202120/30220c9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/75000000/74210000/74202200/74202120/7251e4aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/75000000/74210000/74202200/74202120/676d68a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Northfork Townhouse- walk to all

Greenport

10/10

Exceptional

(5)

"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"

CA $541

CA $1,029 total

includes taxes & fees

Oct 21 - Oct 22

[](https://www.expedia.ca/Greenport-Hotels-Greenport-Village-Townhouse-Walk-To-Town.h74202120.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18770000/18760700/18760693/4aaa8de8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/19000000/18770000/18760700/18760693/20bbb653.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18770000/18760700/18760693/83198fbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/19000000/18770000/18760700/18760693/419a745d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic New England home ,Reunions Beach pass

Guilford

9.2/10

Wonderful

(90)

"House was perfect for family get together. Enjoyed walking into town for afternoon shopping and dining."

CA $316

CA $673 total

includes taxes & fees

Nov 5 - Nov 6

[](https://www.expedia.ca/Guilford-Hotels-Historic-New-England-Home.h18760693.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/96000000/95360000/95352100/95352098/3c0032f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95360000/95352100/95352098/88945e23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/96000000/95360000/95352100/95352098/dc972513.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/96000000/95360000/95352100/95352098/90570d9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gorgeous Greenport Beach House right on the Sound! Breathtaking views

Greenport

9.8/10

Exceptional

(8)

"We came for a girls trip and this property was perfect, had beautiful views and was close to everything...we very much enjoyed our stay!"

[](https://www.expedia.ca/Greenport-Hotels-Gorgeous-Greenport-Beach-House-Right-On-The-Sound-Breathtaking-Views.h95352098.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/7033cd48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/312e44f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, in-room safe, desk, free WiFi](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/24362044.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/f2189685.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### Work and Play Special! Extended Stay Discount

Shelter Island

10/10

Exceptional

(52)

"The house was amazing ,clean and full of good energy.it had everything we needed for peaceful, relaxing getaway serenity now! "

CA $1,123

CA $2,017 total

includes taxes & fees

Nov 12 - Nov 13

[](https://www.expedia.ca/Shelter-Island-Hotels-Work-And-Play-Special-Extended-Stay-Discount-At-A-Hideaway-With-Stellar-Wifi.h39934446.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=2025-10-30&endDate=2025-10-31&regionId=183719&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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Save an average of 15% on thousands of hotels when you're signed in

[Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSouthold-Private-Vacation-Homes.d183719-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouthold-Private-Vacation-Homes.d183719-aaPrivateVacationHomes.Travel-Guide-Accommodation)

## Top Southold Hotel Reviews

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

### Saybrook Point Resort & Marina

10/10 Excellent

"Beautiful property, we loved our room, friendly staff. "

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

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

### Greenporter Hotel

10/10 Excellent

"Parking was really easy. Great location "

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

![Greenview Inn Riverhead](//images.trvl-media.com/lodging/2000000/1380000/1374000/1373980/d1b868c8_y.jpg)

### Greenview Inn Riverhead

10/10 Excellent

"Really clean and new!"

[](https://expedia.ca/Riverhead-Hotels-Greenview-Inn-Riverhead.h1373980.Hotel-Information)

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

### The Bentley Hotel Southampton

10/10 Excellent

"Nice spot"

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

![Pier Blue Inn Old Saybrook - Essex](//images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg)

### Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"Staff was incredibly communicative, kind, and patient. Definitely recommend and we would stay again!"

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

"It was amazing "

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

![Hilton Garden Inn Riverhead](//images.trvl-media.com/lodging/2000000/1970000/1962600/1962521/82ff92d7_y.jpg)

### Hilton Garden Inn Riverhead

10/10 Excellent

"Great atmosphere. Friendly service. Great room. A pleasure to stay here!"

[](https://expedia.ca/Riverhead-Hotels-Hilton-Garden-Inn-Riverhead.h1962521.Hotel-Information)

![Spark by Hilton Guilford](//images.trvl-media.com/lodging/1000000/990000/983200/983128/08241fb2_y.jpg)

### Spark by Hilton Guilford

10/10 Excellent

"Clean and comfortable modern room and bed; helpful staff, especially checking in. Pet friendly is great though my pets stay home."

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

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

### The Sagaponack

10/10 Excellent

"Clean and cute"

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

## Find out more about Southold

## Southold Vacation Homes information

| Number of reviews | 347 |
| --- | --- |
| Accommodation | 1800 Vacation Homes |
| Lowest Price | CA $358 |
| Highest Price | CA $9,039 |

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