Title: Shelter Island, NY Condos for Rent | Expedia.com

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

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## Check prices for these dates

In two weeks

[Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=157359&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=157359&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=157359&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=157359&startDate=2026-06-05&endDate=2026-06-07&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 condo rentals

![One Bedroom Condo King with Ocean view | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/fd0f941b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/804eaa5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![One Bedroom Condo King with Steam Shower | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/a9bb02b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room dining](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/0ca01820.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Offshore Residences

[](https://www.expedia.com/Montauk-Hotels-Offshore-Residences.h118940366.Hotel-Information)

Downtown Montauk

$579 nightly

$662 total

Feb 15 - Feb 16

Total with taxes and fees

[](https://www.expedia.com/Montauk-Hotels-Offshore-Residences.h118940366.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.com/Hotel-Search?startDate=2026-02-26&endDate=2026-02-27&regionId=157359&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Find vacation rentals that suit your style

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=COTTAGE)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=CONDO)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=APARTMENT)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=APART_HOTEL)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=VILLA)

Houseboats

[](https://www.expedia.com/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=HOUSE_BOAT)

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## Top Shelter Island Hotel Reviews

![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

"Clean cozy always enjoy our stay "

[](https://expedia.com/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

"Lovely hotel with great location in town. Great free breakfast and wonderful staff. We will return! "

[](https://expedia.com/Greenport-Hotels-The-Harborfront-Inn.h43532300.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

"Staff was amazing during the snow storm when everything in the town was closed. Also the hotel restaurant was closed so the GM prepared a salad, pasta with chick and stated veg for my husband and me. "

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

"Very comfortable and enjoyable place to stay."

[](https://expedia.com/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.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

"Room was spotless, staff were great and the resort is top notch!!"

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

![Offshore Montauk](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/6944012d_y.jpg)

### Offshore Montauk

10/10 Excellent

"was great."

[](https://expedia.com/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information)

![Montauk Manor](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/96463a2a_y.jpg)

### Montauk Manor

10/10 Excellent

"The room was lovely, the little kitchenette is great. Very quiet and I love the balcony. The staff are great and the restaurant staff at Montis are fantastic "

[](https://expedia.com/Montauk-Hotels-Montauk-Manor.h12694044.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

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

[](https://expedia.com/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

"Adorable room"

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

## Find out more about Shelter Island

## Shelter Island Condo Rentals information

| Number of reviews |                  |
| ----------------- | ---------------- |
| Accommodation     | 43 Condo Rentals |
| Lowest Price      | $662             |
| Highest Price     | $662             |

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- [Flights to Shelter Island Heights ](https://www.expedia.com/Cheap-Flights-To-Shelter-Island-Heights.d183716.Travel-Guide-Flights)
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- [Shelter Island Historical Society ](https://www.expedia.com/Shelter-Island-Historical-Society-Shelter-Island.d553248635961235094.Vacation-Attraction)
- [Havens House ](https://www.expedia.com/Havens-House-Shelter-Island.d6232745.Vacation-Attraction)
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- [Gardiner's Bay Country Club ](https://www.expedia.com/Gardiners-Bay-Country-Club-Shelter-Island.d6282173.Vacation-Attraction)
- [Railroad Museum of Long Island ](https://www.expedia.com/Railroad-Museum-Of-Long-Island-Pipes-Cove.d6327144.Vacation-Attraction)
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- [Shelter Island Heights Vacation Rentals ](https://www.expedia.com/Shelter-Island-Heights-Vacation-Rentals.d183716.Travel-Guide-VacationRentals)
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- [Things to do in Greenport ](https://www.expedia.com/Things-To-Do-In-Greenport.d110728.Travel-Guide-Activities)