Title: Cutchogue Vacation Rentals from CA $250: Short-Term Rentals for 2025 | Expedia.ca

  

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Photo by Adriana T

# Cutchogue Vacation Rentals

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## Check prices for these dates

Tonight

[Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=183659&startDate=2025-10-17&endDate=2025-10-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 18 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=183659&startDate=2025-10-18&endDate=2025-10-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=183659&startDate=2025-10-17&endDate=2025-10-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=183659&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)

## Vacation Rentals in Cutchogue

![Private kitchen](https://images.trvl-media.com/lodging/122000000/121680000/121678200/121678105/f0301ac5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/122000000/121680000/121678200/121678105/1a87907c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/122000000/121680000/121678200/121678105/005911e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/122000000/121680000/121678200/121678105/ed7787f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### New Construction full of amenities

Southampton

CA $480

CA $1,085 total

includes taxes & fees

Oct 31 - Nov 1

[](https://www.expedia.ca/Southampton-Hotels-New-Construction-Full-Of-Amenities.h121678105.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/8e3d5f6a.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)

![Exterior detail](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/b4ee006e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/14ad38a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Clinton

9.2/10

Wonderful

(33)

"Cottage itself clean, but sewage smell in bathroom. Surrounding property derelict motel with ongoing consruction. "

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

michelle

CA $99

CA $250 total

includes taxes & fees

Oct 21 - Oct 22

[](https://www.expedia.ca/Clinton-Hotels-Shalom-Cottage-With-Private-Beach-Rights.h90991445.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/115000000/114540000/114532600/114532580/3a21009d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114540000/114532600/114532580/df2ccd2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114540000/114532600/114532580/827d7818.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/115000000/114540000/114532600/114532580/503155ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Southampton cozy cottage by the beach

Hampton Bays

10/10

Exceptional

(1)

"Great stay. Would stay again. "

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

Weston B.

CA $77

CA $642 total

includes taxes & fees

Oct 20 - Oct 21

[](https://www.expedia.ca/Hampton-Bays-Hotels-Cozy-Beach-Cottage-Steps-To-Meschutt-Beach.h114532580.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)

![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)

![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/98c458f7.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!!"

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

Stephanie M.

CA $4,215

CA $8,172 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)

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

![Private kitchen](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/623abb73.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)

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

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

Westbrook

CA $162

CA $673 total

includes taxes & fees

Nov 4 - Nov 5

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

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

![Condo](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/d9295239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

### Cliffside Resort Condominiums

Greenport

9.0/10

Wonderful

(243)

"Nice location and good for staying with families. The rooms could have been a little cleaner and updated. Hotel communication was excellent for checking in. "

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

dean

CA $315

CA $420 total

includes taxes & fees

Nov 2 - Nov 3

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

![Exterior](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/728215df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/38c1ca05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/a7476bfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/ea540de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Shoreline Oasis

Clinton

9.2/10

Wonderful

(7)

"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"

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

Julie

CA $251

CA $365 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Clinton-Hotels-Shoreline-Oasis.h113308197.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)

![Interior](https://images.trvl-media.com/lodging/35000000/34010000/34005300/34005296/8c3e97ad.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 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)

### 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. "

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

Madelyn G.

CA $2,735

CA $4,807 total

includes taxes & fees

Oct 27 - Oct 28

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/433807ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/825be1b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/a3e46cd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/71856d05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Old Saybrook Center

9.6/10

Exceptional

(38)

"Great property, would stay here again."

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

charles b.

CA $345

CA $720 total

includes taxes & fees

Oct 21 - Oct 22

[](https://www.expedia.ca/Old-Saybrook-Hotels-Luxury-Cottage-Walking-Distance-To-Saybrook-Point-Marina.h72604611.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](https://images.trvl-media.com/lodging/106000000/105960000/105954000/105953994/b0e8e3c1.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)

 

### 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! "

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

James S.

CA $223

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)

![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)

![Exterior](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/aed266db.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)

![Property grounds](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/809e0319.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"

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

Mary M.

CA $139

CA $1,274 total

includes taxes & fees

Oct 20 - Oct 21

[](https://www.expedia.ca/East-Hampton-Hotels-Fall-In-Love-In-East-Hampton.h71000754.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/d416d8d8.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 $5,608

CA $9,125 total

includes taxes & fees

Oct 31 - Nov 1

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

![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)

![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)

### Year-Round Private Jacuzzi / Peaceful Fenced Yard

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 "

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

Jackie S.

CA $139

CA $1,764 total

includes taxes & fees

Oct 20 - Oct 21

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

![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/65eee158.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/c937e03d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/a165f45a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/1eb9ef8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

Greenport

10/10

Exceptional

(1)

"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"

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

Jeannette M.

CA $365

CA $798 total

includes taxes & fees

Oct 20 - Oct 21

[](https://www.expedia.ca/Greenport-Hotels-The-Greenport-Beach-Cottage-3-Min-Walk-To-Beach.h112577488.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/67000000/66960000/66955300/66955225/0611344e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66960000/66955300/66955225/e305ffa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/67000000/66960000/66955300/66955225/d9324980.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/67000000/66960000/66955300/66955225/w1024h767x0y0-f48123b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

Madison

10/10

Exceptional

(33)

"Very much enjoyed our stay!"

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

Barb D.

CA $392

CA $501 total

includes taxes & fees

Oct 20 - Oct 21

[](https://www.expedia.ca/Madison-Hotels-Newly-Renovated-Carriage-House-Near-Town-Beaches.h66955225.Hotel-Information)

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

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

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

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

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

Greenport

9.0/10

Wonderful

(4)

"Great job "

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

emilio

CA $279

CA $428 total

includes taxes & fees

Oct 19 - Oct 20

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

![Smart TV](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/10f54062.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/40dd49e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/b72c2ddb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/f28083b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hidden gem! Southampton beach cottage

Hampton Bays

10/10

Exceptional

(1)

CA $77

CA $631 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Hampton-Bays-Hotels-Water-Views-Cottage-Footsteps-To-Meschutt-Beach.h114533130.Hotel-Information)

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

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

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

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

### Beautifully farmhouse

Southold

10/10

Exceptional

(3)

"good experience"

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

Anonymous traveller

CA $841

CA $1,647 total

includes taxes & fees

Nov 17 - Nov 18

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

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

![Dining](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/4bd4eab0.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."

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

Hanna M.

CA $419

CA $2,057 total

includes taxes & fees

Nov 17 - Nov 18

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

![A heated pool](https://images.trvl-media.com/lodging/51000000/50610000/50607400/50607334/55e69dfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, travel crib, internet](https://images.trvl-media.com/lodging/51000000/50610000/50607400/50607334/861024c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/51000000/50610000/50607400/50607334/bce95391.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/51000000/50610000/50607400/50607334/d0d2900f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Contemporary Southampton Village Home Walking Distance to Town, Pool,...

Southampton

10/10

Exceptional

(15)

"Just finished a 5 day stay. Best house rental ever! Great and thoughtful hosts. Super relaxing and extremely luxurious! Highly recommend!"

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

William H.

CA $2,029

CA $2,947 total

includes taxes & fees

Oct 19 - Oct 20

[](https://www.expedia.ca/Southampton-Hotels-Contemporary-Southampton-Village-Home-Walking-Distance-To-Town.h50607334.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=2025-11-01&endDate=2025-11-02&regionId=183659&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg)

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%2FCutchogue-Vacation-Rentals.d183659.Travel-Guide-VacationRentals)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCutchogue-Vacation-Rentals.d183659.Travel-Guide-VacationRentals)

## Top Cutchogue Hotel Reviews

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

### The Preston House & Hotel

10/10 Excellent

"Staff was amazing, include the restaurants’ staff! 2nd time staying there, will be back for many more!"

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

![ Hampton's Vacation Inn](//images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/4e100a77_y.jpg)

### Hampton's Vacation Inn

10/10 Excellent

"Lovely property. Convenient location. Will stay again. "

[](https://expedia.ca/Hampton-Bays-Hotels-Bowens-By-The-Bays.h10211593.Hotel-Information)

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

### Water's Edge Resort & Spa

10/10 Excellent

"We love the stay everything was perfect"

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

![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)

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

### Spark by Hilton Guilford

10/10 Excellent

"Great"

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

![Bayview Resort](//images.trvl-media.com/lodging/11000000/10460000/10453900/10453825/5ed206f2_y.jpg)

### Bayview Resort

10/10 Excellent

"We love this place. We immediately felt home. Accommodating and helpful. What else can we ask for. :) Though Expedia should do better as a 3rd party by communicating to customers specific conditions and amenities. We are so lucky that Bayview Resort help us a lot. :) Grateful that this weekend was restful and safe. "

[](https://expedia.ca/Hampton-Bays-Hotels-Bayview-Resort.h10453825.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)

## Find out more about Cutchogue

**Everything you need to know about** **Cutchogue** **vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cutchogue vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cutchogue vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Cutchogue vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Cutchogue. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cutchogue vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cutchogue vacation rentals we have selected for you start as low as CA $250 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Cutchogue rentals**

At Expedia, we put the best Cutchogue vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cutchogue rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cutchogue vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cutchogue. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

## Explore a world of travel with Expedia

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-   [Vacation Homes in Cutchogue](https://expedia.ca/Cutchogue-Private-Vacation-Homes.d183659-aaPrivateVacationHomes.Travel-Guide-Accommodation)
-   [Cottages in Cutchogue](https://expedia.ca/Cutchogue-Cottages.d183659-aaCottages.Travel-Guide-Accommodation)
-   [Apartments in Cutchogue](https://expedia.ca/Cutchogue-Apartments.d183659-aaApartments.Travel-Guide-Accommodation)
-   [Villas in Cutchogue](https://expedia.ca/Cutchogue-Villas.d183659-aaVillas.Travel-Guide-Accommodation)
-   [B&B in Cutchogue](https://expedia.ca/Cutchogue-Bed-And-Breakfast.d183659-aaBedAndBreakfast.Travel-Guide-Accommodation)
-   [Condo Rentals in Cutchogue](https://expedia.ca/Cutchogue-Condos.d183659-aaCondos.Travel-Guide-Accommodation)
-   [RV Parks in Cutchogue](https://expedia.ca/Cutchogue-RV-Parks.d183659-aaRVParks.Travel-Guide-Accommodation)
-   [Farmstay in Cutchogue](https://expedia.ca/Cutchogue-Agritourism.d183659-aaAgritourism.Travel-Guide-Accommodation)
-   [Motels in Cutchogue](https://expedia.ca/Cutchogue-Motels.d183659-aaMotels.Travel-Guide-Accommodation)
-   [Aparthotels in Cutchogue](https://expedia.ca/Cutchogue-Apart-Hotels.d183659-aaApartHotels.Travel-Guide-Accommodation)
-   [Resorts in Cutchogue](https://expedia.ca/Cutchogue-Resort-Hotels.d183659-aaResortHotels.Travel-Guide-Accommodation)
-   [Guest Houses in Cutchogue](https://expedia.ca/Cutchogue-Guest-Houses.d183659-aaGuestHouses.Travel-Guide-Accommodation)
-   [Inns in Cutchogue](https://expedia.ca/Cutchogue-Inns.d183659-aaInns.Travel-Guide-Accommodation)
-   [Cabin Rentals in Cutchogue](https://expedia.ca/Cutchogue-Cabins.d183659-aaCabins.Travel-Guide-Accommodation)
-   [Houseboats in Cutchogue](https://expedia.ca/Cutchogue-Houseboats.d183659-aaHouseboats.Travel-Guide-Accommodation)
-   [Chalets in Cutchogue](https://expedia.ca/Cutchogue-Chalets.d183659-aaChalets.Travel-Guide-Accommodation)
-   [Hostels in Cutchogue](https://expedia.ca/Cutchogue-Hostels.d183659-aaHostels.Travel-Guide-Accommodation)
-   [Residences in Cutchogue](https://expedia.ca/Cutchogue-Residences.d183659-aaResidences.Travel-Guide-Accommodation)

## Frequently asked questions

### Are there vacation rentals in Cutchogue?

> Yes, you can find vacation rentals in Cutchogue close to 8 Hands Farm, or you can choose a more secluded option if you want a relaxing stay.

### What are some of the best vacation rentals that Cutchogue has to offer?

> [Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor](https://www.expedia.ca/Bridgehampton-Hotels-Cozy-Bungalow-Available-Nearby-Bridgehampton-And-Sag-Harbor.h105953994.Hotel-Information) : This vacation home rental outside of Cutchogue offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a patio, a garden, and a hot tub so you can immerse yourself in your vacation.

### How many vacation rentals are there in Cutchogue?

> With 45 Expedia vacation rentals, you're sure to find just the right place for your Cutchogue stay.

### What’s there to see and do in Cutchogue?

> Cutchogue Village Green and Fisherman Beach are a couple of lovely local spots to get outside and enjoy nature. While here, Peconic Bay Winery and Bedell Cellars are other places worth a visit.

### What’s a vacation rental in Cutchogue like?

> Vacation rentals are private properties you can stay in for short or long periods in Cutchogue. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from public hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.

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Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app

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