Title: Shelter Island Chalets from CA $108 | Expedia.ca

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# Search Chalets in Shelter Island from CA $108

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## Check prices for these dates

In two weeks

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Feb 27 - Mar 1](https://www.expedia.ca/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 four months

[Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Shelter Island Chalets

No exact matches found, but these alternatives could be just right

## Recommended hotels in Shelter Island

![Ocean View 2 Queens](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/6944012d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/69b11154.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Ocean View 2 Queens with Kitchenette | Private kitchen](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/294d9a91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/6f247566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Offshore Montauk

9.2/10

Wonderful

(74)

"Excellent stay! Gorgeous views, very clean rooms, helpful staff and beautifully done. Will stay again!"

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

Erica

CA $162

CA $265 total

includes taxes & fees

Jan 1 - Jan 2, 2026

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

![Exterior](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/11d8806e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/e77eab74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/04aa4e82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/d096a355.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Motel in Southampton

8.6/10

Excellent

(439)

"Great weekend stay! staff was super kind and property was beautiful! "

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

Chyanne

CA $143

CA $185 total

includes taxes & fees

Dec 6 - Dec 7

[](https://www.expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/afdef753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a48f4b96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/72f65e39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pier Blue Inn Old Saybrook - Essex

8.0/10

Very good

(1000)

"A welcoming place with some nice touches."

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

Leslie

[](https://www.expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information)

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/176892a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/35541bfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Room, 1 King Bed](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/8fa06225.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/78e3666a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Motel in Culloden Shores

8.4/10

Very good

(878)

"Really clean and nice location"

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

Tiara

[](https://www.expedia.ca/Montauk-Hotels-Kennys-Tipperary-Inn.h8474914.Hotel-Information)

![Front of property - evening/night](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/96463a2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/8f0a0367.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)

![Suite, 2 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/37cdbc57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Montauk

9.2/10

Wonderful

(1265)

"Great ambience. Very kind and friendly service. Wonderful luxe suite. Very homey and cozy. I really enjoyed my stay here. Just lovely. "

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

Violet

CA $193

CA $248 total

includes taxes & fees

Dec 11 - Dec 12

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

![Exterior](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/a27d78bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/b026cb5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast area](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/39934cf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/db00678f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Motel in Old Saybrook

7.2/10

Good

(460)

"🙂"

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

Jared

CA $94

CA $108 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Old-Saybrook-Hotels-Econo-Lodge-Inn-Suites-Old-Saybrook-Westbrook.h1177328.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/9371eb14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/691fdd98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/5b4c06e7.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)

### Apartment in Old Lyme

10/10

Exceptional

(3)

"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 $106

CA $270 total

includes taxes & fees

Dec 7 - Dec 8

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

![Property entrance](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/a3a48a86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/2d17124a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Suite, 2 Double Beds, Non Smoking, Kitchenette](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/a4c86ff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Suite, Private Bathroom | Private kitchen](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/c0e14dbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Niantic Inn

9.2/10

Wonderful

(126)

"Easy parking. Walkable dining and to boardwalk. Quaint shopping."

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

Kerry

CA $123

CA $142 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Niantic-Hotels-The-Niantic-Inn.h15001889.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/334e85c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/1bfd9996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/ec2d268d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![55-inch Smart TV with cable channels, TV](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/cbe6e5e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Bentley Hotel Southampton

9.6/10

Exceptional

(390)

"great cost-effective option; room was very spacious and clean."

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

Isadora

CA $154

CA $177 total

includes taxes & fees

Dec 22 - Dec 23

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

![Free self parking](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/7836a152.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free self parking](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/5e85d188.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/7bb1af0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Double Beds](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/d45c604d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Motel in Clinton

8.6/10

Excellent

(296)

"Great staff and clean rooms"

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

Tyler

CA $109

CA $125 total

includes taxes & fees

Dec 8 - Dec 9

[](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.Hotel-Information)

![One Bedroom Harbor View Terrace Suite | View from room](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/a8d80546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/4e8534b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Balcony view](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/64ea9871.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Harbor Front Inn

8.8/10

Excellent

(540)

"Awesome stay!!! Great Location "

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

Bryan

CA $183

CA $277 total

includes taxes & fees

Dec 29 - Dec 30

[](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/8d844436.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, open 9:00 AM to 9:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, Multiple Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/0b15e4f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/8ffa2c0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn Old Saybrook - Westbrook

7.8/10

Good

(1001)

"Staff was kind. Easy, comfortable stay."

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

Jake

CA $141

CA $162 total

includes taxes & fees

Dec 14 - Dec 15

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

![Terrace/patio](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/7564e116.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/f90ba663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/65f0ee8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/509e7634.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Motel in Riverhead

8.4/10

Very good

(707)

"Bed was very comfortable.. staff was very friendly.. loud traffic in AM.. good water pressure.. would stay here again. "

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

Shelly

[](https://www.expedia.ca/Riverhead-Hotels-Shorewood-Inn.h15241380.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/22f2b7c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden Suite King](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/968755d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace King](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/efe41897.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/81035eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Shoals Suites and Slips

9.6/10

Exceptional

(225)

"Beautiful"

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

Linda

CA $238

CA $272 total

includes taxes & fees

Dec 11 - Dec 12

[](https://www.expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information)

![BBQ/picnic area](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/df127760.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bars/lounges, poolside bar](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/1bf554ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/9bf973cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sports facility](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/003f8776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Place Long Island East End

9.2/10

Wonderful

(1001)

"Our room had a great view of the river and marina. we also loved the seating area in the room. Very comfortable"

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

Helen

CA $162

CA $185 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

### Cottage in Hampton Bays

10/10

Exceptional

(1)

CA $77

CA $638 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](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/2000000/1510000/1506700/1506634/e1630145.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/2000000/1510000/1506700/1506634/dc0e4dcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1510000/1506700/1506634/4139664c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/2000000/1510000/1506700/1506634/08b482c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bed & Breakfast in Niantic

9.4/10

Exceptional

(1003)

"Clean great staff great breakfast quiet guests beautiful scenery 10/10"

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

Trey

CA $222

CA $255 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Niantic-Hotels-Inn-At-Harbor-Hill-Marina.h1506634.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/c0b20841.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/ec09d195.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/41a9fc7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Waterford

10/10

Exceptional

(14)

"The property was amazing. The house was very clean and the game room was really fun. It was a very cute place and the backyard was perfect for sitting outside in the afternoon. The beds were really soft and comfortable as well."

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

Jorie M.

CA $199

CA $420 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Waterford-Hotels-Charming-3-Bedroom-Cottage-With-WiFi.h108765994.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/4000000/3010000/3004600/3004551/7e8d204d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/4000000/3010000/3004600/3004551/8ac8989f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/4000000/3010000/3004600/3004551/ad4e87dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast area](https://images.trvl-media.com/lodging/4000000/3010000/3004600/3004551/f50958a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Liberty Inn

7.4/10

Good

(640)

"Great little place to stay with friendly staff and clean room"

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

Carolan

CA $105

CA $121 total

includes taxes & fees

Dec 6 - Dec 7

[](https://www.expedia.ca/Old-Saybrook-Hotels-Liberty-Inn.h3004551.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/5860a5b4.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)

![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)

### Vacation Home in Waterford

10/10

Exceptional

(10)

"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 $131

CA $503 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Waterford-Hotels-Shore-Drive-2-Bedroom2-BathBunkQueen-Oasis.h78355230.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=2025-12-19&endDate=2025-12-20&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

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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=2026-03-05&d1=2026-03-05&endDate=2026-03-08&d2=2026-03-08&lodging=APART_HOTEL)

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=2026-03-05&d1=2026-03-05&endDate=2026-03-08&d2=2026-03-08&lodging=APARTMENT)

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=2026-03-05&d1=2026-03-05&endDate=2026-03-08&d2=2026-03-08&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=2026-03-05&d1=2026-03-05&endDate=2026-03-08&d2=2026-03-08&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=2026-03-05&d1=2026-03-05&endDate=2026-03-08&d2=2026-03-08&lodging=HOUSE_BOAT)

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## Top Shelter Island Hotel Reviews

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

### The Sagaponack

10/10 Excellent

"Clean & amenities, staff friendly Thank you "

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

![Pier Blue Inn Old Saybrook - Essex](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg)

### Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"A welcoming place with some nice touches."

[](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.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

"Lovely rooms and loved the fireplace. Great stay. Awesome few days away from real life!"

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

"Clean and quiet."

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

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

### Montauk Manor

10/10 Excellent

"Great ambience. Very kind and friendly service. Wonderful luxe suite. Very homey and cozy. I really enjoyed my stay here. Just lovely. "

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

"Staff"

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

"The pool was very clean. "

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

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

### Sound View Greenport

10/10 Excellent

"Great room with amazing views! Staff was fantastic and the food was great too"

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

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

### The Atlantic Hotel

10/10 Excellent

"Great hotel for a quick stay - very friendly staff"

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

## Find out more about Shelter Island

## Shelter Island Chalets information

| Number of reviews | 9,540     |
| ----------------- | --------- |
| Accommodation     | 1 Chalets |
| Lowest Price      | CA $108   |
| Highest Price     | CA $638   |

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