Title: Shelter Island Guest Houses from CA $202 | 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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# Search Guest Houses in Shelter Island from CA $202

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## Check prices for these dates

Next weekend

[Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Shelter Island Guest Houses

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/5a24caee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/3da43463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/a79f88d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/f1ad96fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### New and Modern Bridgehampton Accommodations

Bridgehampton

9.6/10

Exceptional

(15)

"Had a great stay here with a small group. Host was very accommodating and responsive. "

CA $246

CA $614 total

includes taxes & fees

Oct 13 - Oct 14

[](https://www.expedia.ca/Bridgehampton-Hotels-New-And-Modern-Bridgehampton-Accommodations.h105953388.Hotel-Information)

![Apartment, 2 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/4e100a77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/6142ad8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/ae2cccbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's activities](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/949a0d23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton's Vacation Inn

Hampton Bays

9.0/10

Wonderful

(317)

"A great Hampton location that's less than a thirty minutes drive from Coopers Beach and South Hampton main street."

CA $176

CA $202 total

includes taxes & fees

Oct 13 - Oct 14

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

![View from property](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/51be5ca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/fdb9f048.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/ae8f0ca6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/d7311f73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### House on Chase Creek

The Heights

9.4/10

Exceptional

(77)

" This was my husband and my first time visiting Shelter Island and I feel lucky that my stay was at the House of ChaseCreek. Bill was excellent in helping us navigate our stay on the Island which made for an enjoyable experience. The house was charming , very clean , and had easy access to the town restaurant s, and Ferry. Highly recommend ! "

CA $259

CA $296 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Shelter-Island-Heights-Hotels-House-On-Chase-Creek.h12610909.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.

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## Top Shelter Island Hotel Reviews

![Montauk Yacht Club](//images.trvl-media.com/lodging/1000000/10000/7000/6970/fcfc464f_y.jpg)

### Montauk Yacht Club

10/10 Excellent

"Staffs were so kind. The place was peaceful and it is really a relaxing place to stay especially it is beach front"

[](https://expedia.ca/Montauk-Hotels-Gurneys-Star-Island-Resort-Marina.h6970.Hotel-Information)

![Sea Crest Resort](//images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/5e6d6769_y.jpg)

### Sea Crest Resort

10/10 Excellent

"Perfect oceanfront with straight on view. Room newly renovated and exceptionally clean. "

[](https://expedia.ca/Amagansett-Hotels-Sea-Crest-Resort.h5232838.Hotel-Information)

![Beachcomber Resort at Montauk](//images.trvl-media.com/lodging/3000000/2220000/2212000/2211971/d4cb08d2_y.jpg)

### Beachcomber Resort at Montauk

10/10 Excellent

"Exceptional in every way"

[](https://expedia.ca/Montauk-Hotels-Beachcomber-At-Montauk.h2211971.Hotel-Information)

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

### The Sagaponack

10/10 Excellent

"Clean and cute"

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

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

### The Bentley Hotel Southampton

10/10 Excellent

"Clean room!!"

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

"Beautiful views"

[](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

"Relaxing wonderful staff!"

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

![Offshore Montauk](//images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/69b11154_y.jpg)

### Offshore Montauk

10/10 Excellent

"Great place."

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

![Sound View Greenport](//images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg)

### Sound View Greenport

10/10 Excellent

"Nice views on sunset"

[](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information)

## Find out more about Shelter Island

## Shelter Island Guest Houses information

| Number of reviews | 408 |
| --- | --- |
| Accommodation | 6 Guest Houses |
| Lowest Price | CA $202 |
| Highest Price | CA $614 |

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-   [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 Guest Houses in Shelter Island on Expedia.com](https://www.expedia.com/Shelter-Island-Guest-Houses.d157359-aaGuestHouses.Travel-Guide-Accommodation)