Title: Shelter Island Vacation Rentals from CA $245: Short-Term Rentals for 2026 | Expedia.ca

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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 rentals

![Lobby](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/4be91ce8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/ec2516ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/aa464430.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/d18d0d4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Montauk Manor

[](https://www.expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information)

Montauk

9.2/10

Wonderful

(1,283 reviews)

"We had a great stay at the Montauk Manor to celebrate my birthday. The room was nice, really comfortable bed and loved the kitchenette. The best part was the view of the sunset in the evening. We enjoyed the restaurant on site as well, Monte’s at the Manor. The heated indoor pool and jacuzzi were perfect, especially due to the cold weather outside. Definitely will return!"

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

Christine

CA $191

CA $245 total

includes taxes & fees

Feb 5 - Feb 6

[](https://www.expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information)

![On the beach](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/150849d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, coffee/tea maker, cookware/dishes/utensils, spices](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/b6de66d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/909788b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/55dd3e1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Old Lyme

10/10

Exceptional

(3 reviews)

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

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

Lylian

CA $126

CA $291 total

includes taxes & fees

Feb 5 - Feb 6

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

![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)

![Property grounds](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/a654b98c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

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

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

Clinton

9.6/10

Exceptional

(34 reviews)

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

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

Benjamin H.

CA $123

CA $263 total

includes taxes & fees

Jan 25 - Jan 26

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

![Smart TV](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/0a5356ac.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)

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

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/765aa668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Seabreeze #3: Cozy Cottage by the beach

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

Hampton Bays

10/10

Exceptional

(1 review)

CA $76

CA $630 total

includes taxes & fees

Jan 29 - Jan 30

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

![Beach nearby](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/3f0d43b0.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)

![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)

### The Bay Cottage · Rocky Neck Park, Beach & Niantic

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

East Lyme

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 $163

CA $499 total

includes taxes & fees

Feb 23 - Feb 24

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

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/106000000/105360000/105355600/105355576/d1477c08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/106000000/105360000/105355600/105355576/94e03953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

### Beach Cottage, private beach and pass

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

East Lyme

10/10

Exceptional

(9 reviews)

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

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

Kerri G.

CA $234

CA $549 total

includes taxes & fees

Feb 5 - Feb 6

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

![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)

![Dining](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/469bf8f7.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)

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

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

Old Lyme

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 $138

CA $574 total

includes taxes & fees

Feb 5 - Feb 6

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

![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)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/9e705245.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

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

Waterford

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 $156

CA $526 total

includes taxes & fees

Feb 5 - Feb 6

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

![Interior](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/0bbae525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/035b4021.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/185a0230.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/c5a2aa07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

[](https://www.expedia.ca/Waterford-Hotels-Cozy-Renovated-Cottage-With-Game-Room.h108765994.Hotel-Information)

Waterford

10/10

Exceptional

(15 reviews)

"We enjoyed our stay! We were able to fit a pack and play for our 1 year old in the game room, which was a fun space. The fenced-in back yard was perfect for our dog. "

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

Christine S.

CA $199

CA $436 total

includes taxes & fees

Jan 24 - Jan 25

[](https://www.expedia.ca/Waterford-Hotels-Cozy-Renovated-Cottage-With-Game-Room.h108765994.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)

![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/cee0fa4c.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)

![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)

### NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

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

Water Mill

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 $5,804

CA $10,038 total

includes taxes & fees

Jan 26 - Jan 27

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

![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124240000/124230600/124230505/d8f17bf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/125000000/124240000/124230600/124230505/w1342h900x0y0-bc9d5238.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/125000000/124240000/124230600/124230505/26414ec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/125000000/124240000/124230600/124230505/332de34a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### #34- Stunning-Newly Remodeled

[](https://www.expedia.ca/Old-Lyme-Hotels-34-Stunning-Newly-Remodeled.h124230505.Hotel-Information)

Old Lyme

CA $265

CA $565 total

includes taxes & fees

Jan 24 - Jan 25

[](https://www.expedia.ca/Old-Lyme-Hotels-34-Stunning-Newly-Remodeled.h124230505.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)

![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/55b895af.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)

![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

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

Westbrook

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 $204

CA $718 total

includes taxes & fees

Jan 27 - Jan 28

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

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

![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/7d654429.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)

### Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

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

Hampon Bays

9.6/10

Exceptional

(23 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 $1,814 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)

![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123640000/123634200/123634189/bc4d2a3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/123640000/123634200/123634189/484237c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/124000000/123640000/123634200/123634189/b6eaff49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/123640000/123634200/123634189/3a7fb390.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quintessential Essex. Steps from the Steam Train!

[](https://www.expedia.ca/Essex-Hotels-Quintessential-Essex-Steps-From-The-Steam-Train.h123634189.Hotel-Information)

Essex

CA $219

CA $425 total

includes taxes & fees

Feb 5 - Feb 6

[](https://www.expedia.ca/Essex-Hotels-Quintessential-Essex-Steps-From-The-Steam-Train.h123634189.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)

![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)

![Exterior](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/aed266db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Blackberry: Private home with jacuzzi year-round

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

East Hampton

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 $136

CA $1,326 total

includes taxes & fees

Feb 19 - Feb 20

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

![Pool](https://images.trvl-media.com/lodging/124000000/123140000/123130700/123130625/40ddf6c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123140000/123130700/123130625/862a4632.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/124000000/123140000/123130700/123130625/1d0cab84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/124000000/123140000/123130700/123130625/fde884e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Amagansett Farmhouse Retreat - Outdoor Fireplace & Basement Arcade, Great for Kids

[](https://www.expedia.ca/East-Hampton-Hotels-Amagansett-Farmhouse-Retreat.h123130625.Hotel-Information)

East Hampton North

CA $194

CA $953 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/East-Hampton-Hotels-Amagansett-Farmhouse-Retreat.h123130625.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)

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

![Exterior](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/2a31845e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish Modern Stay Steps from the Ocean

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

Clinton

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 $223

CA $465 total

includes taxes & fees

Feb 8 - Feb 9

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

![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)

![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/a31fd902.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

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

Clinton

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 $186

CA $729 total

includes taxes & fees

Feb 10 - Feb 11

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

![Private kitchen](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/1190496c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/ef1a1d3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/5689ac07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/110000000/109670000/109662700/109662697/253d38d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Canoe Place Waterfront Residences

[](https://www.expedia.ca/Hampton-Bays-Hotels-Canoe-Place-Waterfront-Residences.h109662697.Hotel-Information)

Hampton Bays

10/10

Exceptional

(1 review)

CA $1,701

CA $2,061 total

includes taxes & fees

Jan 29 - Jan 30

[](https://www.expedia.ca/Hampton-Bays-Hotels-Canoe-Place-Waterfront-Residences.h109662697.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)

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

![Marina](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/4422918e.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)

### Black Swan: Beachfront Home w/ Year-Round Jacuzzi

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

Hampton Bays

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 $1,729 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)

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=2026-02-06&endDate=2026-02-07&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

[](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=2026-04-22&d1=2026-04-22&endDate=2026-04-25&d2=2026-04-25&lodging=VACATION_HOME)

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=2026-04-22&d1=2026-04-22&endDate=2026-04-25&d2=2026-04-25&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=2026-04-22&d1=2026-04-22&endDate=2026-04-25&d2=2026-04-25&lodging=APARTMENT)

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=2026-04-22&d1=2026-04-22&endDate=2026-04-25&d2=2026-04-25&lodging=APART_HOTEL)

Condos

[](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=2026-04-22&d1=2026-04-22&endDate=2026-04-25&d2=2026-04-25&lodging=CONDO)

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=2026-04-22&d1=2026-04-22&endDate=2026-04-25&d2=2026-04-25&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=2026-04-22&d1=2026-04-22&endDate=2026-04-25&d2=2026-04-25&lodging=HOUSE_BOAT)

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## Top Shelter Island Hotel Reviews

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

### Saybrook Point Resort & Marina

10/10 Excellent

"All was good at the hotel. No complaints"

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

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

### The Preston House & Hotel

10/10 Excellent

"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)

![Montauk Blue Hotel](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/f520a49e_y.jpg)

### Montauk Blue Hotel

10/10 Excellent

"Great view of sunrise and sunset "

[](https://expedia.ca/Montauk-Hotels-Montauk-Blue-Hotel.h105612509.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)

## Find out more about Shelter Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Shelter Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Vacation Homes in Shelter Island ](https://expedia.ca/Shelter-Island-Private-Vacation-Homes.d157359-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Shelter Island ](https://expedia.ca/Shelter-Island-Cottages.d157359-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Shelter Island ](https://expedia.ca/Shelter-Island-Apartments.d157359-aaApartments.Travel-Guide-Accommodation)
- [Condo Rentals in Shelter Island ](https://expedia.ca/Shelter-Island-Condos.d157359-aaCondos.Travel-Guide-Accommodation)
- [B&B in Shelter Island ](https://expedia.ca/Shelter-Island-Bed-And-Breakfast.d157359-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Villas in Shelter Island ](https://expedia.ca/Shelter-Island-Villas.d157359-aaVillas.Travel-Guide-Accommodation)
- [Motels in Shelter Island ](https://expedia.ca/Shelter-Island-Motels.d157359-aaMotels.Travel-Guide-Accommodation)
- [RV Parks in Shelter Island ](https://expedia.ca/Shelter-Island-RV-Parks.d157359-aaRVParks.Travel-Guide-Accommodation)
- [Resorts in Shelter Island ](https://expedia.ca/Shelter-Island-Resort-Hotels.d157359-aaResortHotels.Travel-Guide-Accommodation)
- [Farmstay in Shelter Island ](https://expedia.ca/Shelter-Island-Agritourism.d157359-aaAgritourism.Travel-Guide-Accommodation)
- [Aparthotels in Shelter Island ](https://expedia.ca/Shelter-Island-Apart-Hotels.d157359-aaApartHotels.Travel-Guide-Accommodation)
- [Inns in Shelter Island ](https://expedia.ca/Shelter-Island-Inns.d157359-aaInns.Travel-Guide-Accommodation)
- [Guest Houses in Shelter Island ](https://expedia.ca/Shelter-Island-Guest-Houses.d157359-aaGuestHouses.Travel-Guide-Accommodation)
- [Houseboats in Shelter Island ](https://expedia.ca/Shelter-Island-Houseboats.d157359-aaHouseboats.Travel-Guide-Accommodation)
- [Cabin Rentals in Shelter Island ](https://expedia.ca/Shelter-Island-Cabins.d157359-aaCabins.Travel-Guide-Accommodation)
- [Chalets in Shelter Island ](https://expedia.ca/Shelter-Island-Chalets.d157359-aaChalets.Travel-Guide-Accommodation)
- [Hostels in Shelter Island ](https://expedia.ca/Shelter-Island-Hostels.d157359-aaHostels.Travel-Guide-Accommodation)
- [Condo Resorts in Shelter Island ](https://expedia.ca/Shelter-Island-Condominium-Resort.d157359-aaCondominiumResort.Travel-Guide-Accommodation)
- [Residences in Shelter Island ](https://expedia.ca/Shelter-Island-Residences.d157359-aaResidences.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find vacation rentals in Shelter Island?

### What are some of the best vacation home rentals that Shelter Island has to offer?

### How many vacation rentals are there in Shelter Island?

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- [Beach Hotel in Plattsburgh](https://expedia.ca/Plattsburgh-Hotels-Beach-Hotel.0-0-d2816-tBeachHotel.Travel-Guide-Filter-Hotels)

Flights

- [Cheap Flights from Plattsburgh](https://expedia.ca/lp/flights/2816/flights-from-plattsburgh)
- [Cheap Flights from Syracuse](https://expedia.ca/lp/flights/601764/flights-from-syracuse)

Activities

- [Things to do in Albany](https://expedia.ca/Things-To-Do-In-Albany.d603260.Travel-Guide-Activities)
- [Things to do in Syracuse](https://expedia.ca/Things-To-Do-In-Syracuse.d601764.Travel-Guide-Activities)
- [Things to do in Niagara Falls](https://expedia.ca/Things-To-Do-In-Niagara-Falls.d602721.Travel-Guide-Activities)
- [Things to do in Alexandria Bay](https://expedia.ca/Things-To-Do-In-Alexandria-Bay.d10739.Travel-Guide-Activities)

Packages

- [Niagara Falls Vacations](https://expedia.ca/Niagara-Falls.d602721.Destination-Travel-Guides)

General

- [Visit Ellicottville](https://expedia.ca/Ellicottville.dx183669)
- [Visit Saratoga Springs](https://expedia.ca/Saratoga-Springs.dx9775)
- [Visit Niagara Falls](https://expedia.ca/Niagara-Falls.dx602721)
- [Visit Montauk](https://expedia.ca/Montauk.dx10637)
- [Visit Lake Placid](https://expedia.ca/Lake-Placid.dx6055989)

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