Title: Shelter Island Vacation Home Rentals from CA $294: Search Top Private Vacation Homes for Rent | Expedia.ca

[Shelter Island Travel Guide](https://expedia.ca/Shelter-Island.dx157359)[Hotels in Shelter Island](https://expedia.ca/Shelter-Island-Hotels.d157359.Travel-Guide-Hotels)[Vacation Rentals in Shelter Island](https://expedia.ca/Shelter-Island-Vacation-Rentals.d157359.Travel-Guide-VacationRentals)[Flights to Shelter Island](https://expedia.ca/Cheap-Flights-To-Shelter-Island.d157359.Travel-Guide-Flights)[Things to do in Shelter Island](https://expedia.ca/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities)[Shelter Island Car Rentals](https://expedia.ca/Car-Rentals-In-Shelter-Island.d157359.Car-Rental-Guide)[Shelter Island Vacation Packages](https://expedia.ca/Shelter-Island.d157359.Destination-Travel-Guides)

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## Check prices for these dates

In two weeks

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=157359&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=157359&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=157359&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=157359&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)

## Our top choices for Shelter Island vacation homes

![Beach nearby](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/3f0d43b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/17c0663e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/878d2c1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/3a7a158a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in East Lyme

[](https://www.expedia.ca/Niantic-Hotels-The-Bay-Cottage-Rocky-Neck-Park.h109114296.Hotel-Information)

9.0/10

Wonderful

(4 reviews)

"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."

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

Sarah G.

CA $164

CA $501 total

includes taxes & fees

Jan 23 - Jan 24

[](https://www.expedia.ca/Niantic-Hotels-The-Bay-Cottage-Rocky-Neck-Park.h109114296.Hotel-Information)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/d4679987.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/544c1919.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/1c55c50b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/ca71fb83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Waterford

[](https://www.expedia.ca/Waterford-Hotels-Shore-Drive-2-Bedroom2-BathBunkQueen-Oasis.h78355230.Hotel-Information)

10/10

Exceptional

(11 reviews)

"We had a nice stay. Kitchen well stocked and house was clean and comfortable."

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

Elaine A.

CA $159

CA $531 total

includes taxes & fees

Feb 4 - Feb 5

[](https://www.expedia.ca/Waterford-Hotels-Shore-Drive-2-Bedroom2-BathBunkQueen-Oasis.h78355230.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/eea5c652.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/95b993b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/e689a456.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/a31fd902.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Clinton

[](https://www.expedia.ca/Clinton-Hotels-The-Cozy-Glass-House.h107779041.Hotel-Information)

10/10

Exceptional

(3 reviews)

"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "

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

Elya D.

CA $161

CA $699 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Clinton-Hotels-The-Cozy-Glass-House.h107779041.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/87f067c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/423fe469.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/01fcfbdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/469bf8f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Old Lyme

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

10/10

Exceptional

(5 reviews)

"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!"

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

Hemie J.

CA $139

CA $576 total

includes taxes & fees

Jan 26 - Jan 27

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

![Private kitchen](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/021898ba.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)

### Vacation Home in Westbrook

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

10/10

Exceptional

(1 review)

"Perfect house for 6 guests. Loved that it was close to the beach."

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

Shannon G.

CA $214

CA $732 total

includes taxes & fees

Jan 27 - Jan 28

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

![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/c520cfc2.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/f04ef5e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/d4c45248.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/41d30343.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Water Mill

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

10/10

Exceptional

(6 reviews)

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

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

Stephanie M.

CA $5,800

CA $10,025 total

includes taxes & fees

Feb 3 - Feb 4

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

![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)

![Dining](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/146ca0d3.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)

### Vacation Home in East Hampton

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

9.0/10

Wonderful

(4 reviews)

"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "

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

Suzanne R.

CA $137

CA $1,353 total

includes taxes & fees

Feb 8 - Feb 9

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

![1 bedroom, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/ca1c5177.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 $178

CA $294 total

includes taxes & fees

Jan 25 - Jan 26

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

![Outdoor dining](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/252d3a5c.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/w4243h2825x0y0-3e3183ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/ceb7120d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/w4242h2825x0y0-4fbf9283.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Hampon Bays

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

9.6/10

Exceptional

(22 reviews)

"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"

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

Annie B.

CA $137

CA $1,813 total

includes taxes & fees

Jan 25 - Jan 26

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

![Property grounds](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/9e16b0d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/00ea4ccc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/89dee084.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/6f35c24c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Clinton

[](https://www.expedia.ca/Clinton-Hotels-Stylish-Modern-Stay-Steps-From-The-Ocean.h120150878.Hotel-Information)

10/10

Exceptional

(1 review)

"Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. "

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

Kelly Z.

CA $224

CA $467 total

includes taxes & fees

Jan 23 - Jan 24

[](https://www.expedia.ca/Clinton-Hotels-Stylish-Modern-Stay-Steps-From-The-Ocean.h120150878.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/84a27bf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor banquet area](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/997596e4.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)

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

### Vacation Home in Hampton Bays

[](https://www.expedia.ca/Hampton-Bays-Hotels-Black-Swan-Beachfront-Home-W-Year-Round-Jacuzzi.h92502496.Hotel-Information)

9.6/10

Exceptional

(14 reviews)

"Nice house. Photos and descriptions represent it very accurately. "

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

Will K.

CA $208

CA $1,728 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Hampton-Bays-Hotels-Black-Swan-Beachfront-Home-W-Year-Round-Jacuzzi.h92502496.Hotel-Information)

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

![Dining](https://images.trvl-media.com/lodging/114000000/113440000/113439500/113439409/4c26b39e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113440000/113439500/113439409/10a94b38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Bay Point

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

CA $6,226

CA $8,670 total

includes taxes & fees

Jan 25 - Jan 26

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

![Outdoor dining](https://images.trvl-media.com/lodging/24000000/23150000/23145000/23144923/c63e0b0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/24000000/23150000/23145000/23144923/d639410c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/24000000/23150000/23145000/23144923/a349b7f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/24000000/23150000/23145000/23144923/8b7ef6eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Waterford

[](https://www.expedia.ca/Waterford-Hotels-Coastal-New-England-Waterfront-Home.h23144923.Hotel-Information)

10/10

Exceptional

(126 reviews)

"Great property!"

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

Matthew B.

CA $455

CA $853 total

includes taxes & fees

Jan 23 - Jan 24

[](https://www.expedia.ca/Waterford-Hotels-Coastal-New-England-Waterfront-Home.h23144923.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h946x0y0-a3c0ca5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h956x0y0-f00664d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h959x0y0-51b04f4c.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)

### Vacation Home in Saybrook Manor

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

9.6/10

Exceptional

(134 reviews)

"We loved our stay!"

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

Deana L.

CA $311

CA $758 total

includes taxes & fees

Jan 25 - Jan 26

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

![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/107000000/106350000/106340600/106340524/c1360527.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/107000000/106350000/106340600/106340524/b56aaa31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/107000000/106350000/106340600/106340524/5b429221.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, computer monitors, printers](https://images.trvl-media.com/lodging/107000000/106350000/106340600/106340524/fed3485d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Laurel

[](https://www.expedia.ca/Laurel-Hotels-Beach-Cottage.h106340524.Hotel-Information)

10/10

Exceptional

(1 review)

CA $416

CA $1,178 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Laurel-Hotels-Beach-Cottage.h106340524.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/120000000/119900000/119891500/119891409/w905h683x60y0-297b69ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/120000000/119900000/119891500/119891409/w906h683x58y0-bc7fef2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/120000000/119900000/119891500/119891409/w905h683x60y0-eb7cd670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, internet](https://images.trvl-media.com/lodging/120000000/119900000/119891500/119891409/w904h683x60y0-a596b0d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Wainscott

[](https://www.expedia.ca/Wainscott-Hotels-Cozy-5-Bedroom-With-Wi-Fi-And-Air-Condition.h119891409.Hotel-Information)

CA $2,067

CA $2,690 total

includes taxes & fees

Jan 22 - Jan 23

[](https://www.expedia.ca/Wainscott-Hotels-Cozy-5-Bedroom-With-Wi-Fi-And-Air-Condition.h119891409.Hotel-Information)

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

![Outdoor dining](https://images.trvl-media.com/lodging/51000000/50610000/50607400/50607334/626c7bcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

![Interior](https://images.trvl-media.com/lodging/51000000/50610000/50607400/50607334/115709ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Southampton

[](https://www.expedia.ca/Southampton-Hotels-Contemporary-Southampton-Village-Home-Walking-Distance-To-Town.h50607334.Hotel-Information)

10/10

Exceptional

(15 reviews)

"We loved our stay here it was a lovely, warm and beautifully appointed home with a great pool and walkable to town. We hope to be able to return here again soon!"

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

Deborah V.

CA $1,578

CA $2,199 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Southampton-Hotels-Contemporary-Southampton-Village-Home-Walking-Distance-To-Town.h50607334.Hotel-Information)

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

![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74210000/74202200/74202120/65a3c504.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)

![Smart TV](https://images.trvl-media.com/lodging/75000000/74210000/74202200/74202120/fdd8564b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Greenport

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

10/10

Exceptional

(5 reviews)

"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"

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

Beth R.

CA $398

CA $843 total

includes taxes & fees

Jan 25 - Jan 26

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

![Interior](https://images.trvl-media.com/lodging/71000000/70870000/70866200/70866153/3063b965.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, foosball, table tennis](https://images.trvl-media.com/lodging/71000000/70870000/70866200/70866153/ba457ef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/71000000/70870000/70866200/70866153/96f2554e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/71000000/70870000/70866200/70866153/be5ccde8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Hampton Bays

[](https://www.expedia.ca/Hampton-Bays-Hotels-Cozy-Hamptons-Escape-3BR-Minutes-From-Beach.h70866153.Hotel-Information)

9.2/10

Wonderful

(5 reviews)

"Great place. It's exactly like the listing! Would stay again!"

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

Taylor H.

CA $1,660

CA $2,118 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Hampton-Bays-Hotels-Cozy-Hamptons-Escape-3BR-Minutes-From-Beach.h70866153.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95360000/95352100/95352098/w1440h957x0y3-4708a518.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/96000000/95360000/95352100/95352098/907ffc74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95360000/95352100/95352098/9392204d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95360000/95352100/95352098/28ef29e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Greenport

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

9.6/10

Exceptional

(10 reviews)

"Super location - just near The beautiful village of Greenport with a sweeping view of the bay, A very happy house - super Clean, and we had everything that we needed. Meghan was a wonderful host, and answered us quickly with any question that we had. I loved the NorthFork and this home was the perfect place to stay!"

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

Carine J.

CA $560

CA $1,111 total

includes taxes & fees

Jan 22 - Jan 23

[](https://www.expedia.ca/Greenport-Hotels-Gorgeous-Greenport-Beach-House-Right-On-The-Sound-Breathtaking-Views.h95352098.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=2026-02-04&endDate=2026-02-05&regionId=157359&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Private vacation homes

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Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-04-21&d1=2026-04-21&endDate=2026-04-24&d2=2026-04-24&lodging=COTTAGE)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-04-21&d1=2026-04-21&endDate=2026-04-24&d2=2026-04-24&lodging=APARTMENT)

Condos

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Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-04-21&d1=2026-04-21&endDate=2026-04-24&d2=2026-04-24&lodging=APART_HOTEL)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-04-21&d1=2026-04-21&endDate=2026-04-24&d2=2026-04-24&lodging=VILLA)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-04-21&d1=2026-04-21&endDate=2026-04-24&d2=2026-04-24&lodging=HOUSE_BOAT)

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## Top Shelter Island Hotel Reviews

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

### The Preston House & Hotel

10/10 Excellent

"Wonderful experience at the Preston. Inspite of the broken elevator the entire staff went out of their ways to make our stay top self Danielle the front desk person helped us with our bags and each morning helped to carry breakfast to the room. The bartender was delightful and very personable and made good driks. Famtastic time in a great hotel. Thanks to the entire staff."

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

"Was a clean room and the pool was warm and kids had fun. Breakfast was good and plenty of choices "

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

"room was very clean and the staff is great love the Bentley"

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

"Great room and staff"

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

![Hyatt Place Long Island East End](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/9bf973cb_y.jpg)

### Hyatt Place Long Island East End

10/10 Excellent

"Front desk staff and cleanliness of room."

[](https://expedia.ca/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.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)

![Gurney's Montauk Resort & Seawater Spa](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/895004c9_y.jpg)

### Gurney's Montauk Resort & Seawater Spa

10/10 Excellent

"Staying at Gurney's after their many renovations was surprising !! The rooms don't look outdated anymore including the Spa / Pool area - for the price you're paying per night, I appreciated the face lift. Oceanviews from any angle of this hotel site will always be incredible ! "

[](https://expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information)

![The Atlantic Hotel](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg)

### The Atlantic Hotel

10/10 Excellent

"Staff was very friendly room was clean and comfortable "

[](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information)

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

### Saybrook Point Resort & Marina

10/10 Excellent

"Perfect ❤️"

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

## Find out more about Shelter Island

## Shelter Island Vacation Homes information

| Number of reviews | 292                 |
| ----------------- | ------------------- |
| Accommodation     | 1792 Vacation Homes |
| Lowest Price      | CA $294             |
| Highest Price     | CA $10,025          |

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- [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)
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- [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)
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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)
- [Cheap Hotels in Southold ](https://www.expedia.ca/Southold-Hotels-Cheap-Hotels.0-0-d183719-tCheapHotels.Travel-Guide-Filter-Hotels)
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- [Hotels near Wades Beach ](https://www.expedia.ca/Wades-Beach-Hotels.0-l553248621554204759-0.Travel-Guide-Filter-Hotels)

- [Flights to Greenport ](https://www.expedia.ca/Cheap-Flights-To-Greenport.d110728.Travel-Guide-Flights)
- [Flights from Southold ](https://www.expedia.ca/lp/flights/183719/flights-from-southold)
- [Flights from North Haven ](https://www.expedia.ca/lp/flights/553248634998589872/flights-from-north-haven)
- [Flights from East Marion ](https://www.expedia.ca/lp/flights/6069914/flights-from-east-marion)
- [Flights from Orient ](https://www.expedia.ca/lp/flights/6326191/flights-from-orient)
- [Flights from Toronto (YYZ) to New York (NYC) ](https://www.expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york)

- [Visit East Marion ](https://www.expedia.ca/East-Marion.dx6069914)
- [Visit Pipes Cove ](https://www.expedia.ca/Greenport-Pipes-Cove.dx553248635976473295)
- [Kontokosta Winery ](https://www.expedia.ca/Kontokosta-Winery-Greenport.d6326928.Vacation-Attraction)
- [Visit North Haven ](https://www.expedia.ca/North-Haven.dx553248634998589872)
- [Orient Vacations ](https://www.expedia.ca/Orient.d6326191.Destination-Travel-Guides)
- [Visit Bay Point ](https://www.expedia.ca/Sag-Harbor-Bay-Point.dx553248635976471151)
- [Visit Sag Harbor ](https://www.expedia.ca/Sag-Harbor.dx154327)
- [Shelter Island Heights Vacations ](https://www.expedia.ca/Shelter-Island-Heights.d183716.Destination-Travel-Guides)

- [Car rental Greenport ](https://www.expedia.ca/Car-Rentals-In-Greenport.d110728.Car-Rental-Guide)
- [Car rental Orient ](https://www.expedia.ca/Car-Rentals-In-Orient.d6326191.Car-Rental-Guide)

- [Things to do in Greenport ](https://www.expedia.ca/Things-To-Do-In-Greenport.d110728.Travel-Guide-Activities)
- [Things to do in Sag Harbor ](https://www.expedia.ca/Things-To-Do-In-Sag-Harbor.d154327.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)

- [Book Vacation Homes in Shelter Island on Expedia.com ](https://www.expedia.com/Shelter-Island-Private-Vacation-Homes.d157359-aaPrivateVacationHomes.Travel-Guide-Accommodation)