Title: Shelter Island Vacation Rentals from CA $231: Short-Term Rentals for 2025 | Expedia.ca

  

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Photo by tom owens

# Shelter Island Vacation Rentals

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## Check prices for these dates

Tonight

[Oct 24 - Oct 25](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-24&endDate=2025-10-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-25&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

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

Next weekend

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Vacation Rentals in Shelter Island

![Property grounds](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/7033cd48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/f2189685.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/312e44f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, in-room safe, desk, free WiFi](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/24362044.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### Work and Play Special! Extended Stay Discount

Shelter Island

10/10

Exceptional

(52)

"Really great property, had a relaxing lovely time!"

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

Nava S.

CA $1,007

CA $1,862 total

includes taxes & fees

Nov 5 - Nov 6

[](https://www.expedia.ca/Shelter-Island-Hotels-Work-And-Play-Special-Extended-Stay-Discount-At-A-Hideaway-With-Stellar-Wifi.h39934446.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)

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

![Lobby](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/4be91ce8.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)

### Montauk Manor

Montauk

9.2/10

Wonderful

(1257)

"Beautiful grounds, excellent staff"

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

Jess

CA $212

CA $269 total

includes taxes & fees

Nov 3 - Nov 4

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

![Apartment | Private kitchen](https://images.trvl-media.com/lodging/12000000/11070000/11062900/11062836/4604b12d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/12000000/11070000/11062900/11062836/de9e44d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | Private kitchen](https://images.trvl-media.com/lodging/12000000/11070000/11062900/11062836/e03ad839.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | Private kitchen](https://images.trvl-media.com/lodging/12000000/11070000/11062900/11062836/4c252ffa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Montauk Oceanside Suites

Downtown Montauk

8.6/10

Excellent

(415)

"We loved it, suite size was great! "

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

Patrick

CA $190

CA $233 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Montauk-Hotels-Born-Free-Suites-By-The-Sea.h11062836.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/1638a16b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Condo](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/fa408cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Condo | Living area](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/w1446h1293x1y0-077b519e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Condo](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/d9295239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cliffside Resort Condominiums

Greenport

9.0/10

Wonderful

(244)

"Nice location and good for staying with families. The rooms could have been a little cleaner and updated. Hotel communication was excellent for checking in. "

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

dean

CA $313

CA $419 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Greenport-Hotels-Cliffside-Resort-Condominiums.h10449005.Hotel-Information)

![Ocean View 2BD Corner King and Queen | Living area](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/23c43d21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/213ea8fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/27ca1ee9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Ocean View 2BD Corner King and Queen | Private kitchen](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/5974dc7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Windward Shores Ocean Resort

Amagansett

8.8/10

Excellent

(300)

"Quiet place, went off season, cooked all meals in the room, good home base to explore the area."

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

Jerry

[](https://www.expedia.ca/Amagansett-Hotels-Windward-Shores-Ocean-Resort.h4207136.Hotel-Information)

![Apartment, 1 Bedroom | Private kitchen](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207142/59e33701.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207142/9880dce6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 1 Bedroom | Private kitchen](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207142/6b2173cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207142/14ba9bab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Driftwood Resort

Montauk

9.0/10

Wonderful

(235)

"Great place to stay for small family "

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

DongHo

CA $201

CA $276 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Montauk-Hotels-Driftwood-Resort.h4207142.Hotel-Information)

![TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/27000000/26560000/26554100/26554014/20bccc6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/27000000/26560000/26554100/26554014/2c2582eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/27000000/26560000/26554100/26554014/95829c96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/27000000/26560000/26554100/26554014/9341740d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

Montauk

8.8/10

Excellent

(28)

"This adorable, cozy cottage was perfect for our family getaway to Montauk. We have tried various rentals and hotels each summer and Robert’s cottage was by far our favorite. It fit our family of 5 perfectly, with enough room that we didn’t feel on top of each other. The decor was light and airy and just what we were hoping to find. From the awesome location, just a walk to the ocean, to the indoor pool and back up to a comfortable stay, our entire family agree that we can’t wait to return!...

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

Allie G.

[](https://www.expedia.ca/Montauk-Hotels-Oceanfront.h26554014.Hotel-Information)

![On the beach, white sand](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207128/1ba7bf71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Courtside Two Bedroom](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207128/1c56664c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, Ocean View](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207128/f8e91815.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207128/c514c91d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Surf Club

Montauk

8.6/10

Excellent

(280)

"Very close walk to the beach great for little ones "

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

Cara Ann

[](https://www.expedia.ca/Montauk-Hotels-The-Surf-Club.h4207128.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/106000000/105960000/105954000/105953994/c1c14546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sun loungers, beach towels](https://images.trvl-media.com/lodging/106000000/105960000/105954000/105953994/618fa7d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105960000/105954000/105953994/b0e8e3c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/106000000/105960000/105954000/105953994/9a2f74fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Bridgehampton

9.6/10

Exceptional

(15)

"We had a one-night stay at this location. It was perfect for us from many perspectives and we enjoyed staying there. Very nice place!Thanks! "

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

James S.

CA $220

CA $523 total

includes taxes & fees

Oct 28 - Oct 29

[](https://www.expedia.ca/Bridgehampton-Hotels-Cozy-Bungalow-Available-Nearby-Bridgehampton-And-Sag-Harbor.h105953994.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/33000000/32530000/32523000/32522969/4c400fa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32530000/32523000/32522969/270-800f5613.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, sun loungers](https://images.trvl-media.com/lodging/33000000/32530000/32523000/32522969/bf812e72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/33000000/32530000/32523000/32522969/c5a193ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### MONTAUK MANOR-DELUXE STUDIO APARTMENT

MONTAUK

9.8/10

Exceptional

(76)

"Our stay was excellent however the bed in our room was as firm as bricks, needed to use the mattress from the pull out couch to put on top of the bed, tried to sleep on the pull out first but you can feel the springs."

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

Dietmar S.

[](https://www.expedia.ca/Montauk-Hotels-MONTAUK-MANOR-DELUXE-STUDIO-APARTMENT.h32522969.Hotel-Information)

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

![Property grounds](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/14ad38a9.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, 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)

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

Clinton

9.2/10

Wonderful

(33)

"Cottage itself clean, but sewage smell in bathroom. Surrounding property derelict motel with ongoing consruction. "

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

michelle

CA $96

CA $246 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Clinton-Hotels-Shalom-Cottage-With-Private-Beach-Rights.h90991445.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/67000000/66960000/66955300/66955225/0611344e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/67000000/66960000/66955300/66955225/d9324980.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66960000/66955300/66955225/e305ffa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/67000000/66960000/66955300/66955225/cffe2e62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

Madison

10/10

Exceptional

(33)

"Very much enjoyed our stay!"

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

Barb D.

CA $434

CA $555 total

includes taxes & fees

Oct 29 - Oct 30

[](https://www.expedia.ca/Madison-Hotels-Newly-Renovated-Carriage-House-Near-Town-Beaches.h66955225.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/68000000/67410000/67408600/67408597/8db1b1e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/68000000/67410000/67408600/67408597/59786c41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/68000000/67410000/67408600/67408597/248b2170.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/68000000/67410000/67408600/67408597/9db89f13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Old Saybrook

10/10

Exceptional

(34)

"Enjoyed our stay"

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

Nicole L.

[](https://www.expedia.ca/Old-Saybrook-Hotels-Oceanfront-Oasis-Spacious-3-Bedroom.h67408597.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33570000/33561600/33561503/ca104a55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33570000/33561600/33561503/850fe737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33570000/33561600/33561503/a543eee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/34000000/33570000/33561600/33561503/ae5634ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Hampton Bays

9.6/10

Exceptional

(141)

"Perfect property to hangout and stay entertained for hours"

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

Ryder I.

[](https://www.expedia.ca/Hampton-Bays-Hotels-Beautiful-Waterfront.h33561503.Hotel-Information)

![One Bedroom Condo King with Steam Shower | Living area](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/fa3ad3aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![One Bedroom Condo King with Steam Shower](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/80b0c655.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![One Bedroom Condo King with Steam Shower | Terrace/patio](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/8db6a5b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Offshore Residences

Downtown Montauk

CA $740

CA $1,005 total

includes taxes & fees

Oct 26 - Oct 27

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

![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)

![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)

![Interior](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/5b4c06e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

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 $72

CA $231 total

includes taxes & fees

Nov 19 - Nov 20

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

![On the beach](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147909/7879bd22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147909/6410aa9b.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/107000000/106150000/106148000/106147909/a8147226.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147909/94eada8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Freeboard at Soundview · Beach+Ocean+Sunrise

Old Lyme

9.4/10

Exceptional

(6)

"It was very close to the beach , quiet, parking on property room had everything you would need i enjoyed my stay didnt want to leave so soon wouldve liked at least 1 more day maybe next year thank you. "

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

Dana

CA $72

CA $231 total

includes taxes & fees

Oct 28 - Oct 29

[](https://www.expedia.ca/Old-Lyme-Hotels-Freeboard-At-Soundview-BeachOceanViewSunrise.h106147909.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/102000000/101880000/101877700/101877657/05048f3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, table tennis, books, stereo](https://images.trvl-media.com/lodging/102000000/101880000/101877700/101877657/70e808a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101880000/101877700/101877657/dc64ecc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/102000000/101880000/101877700/101877657/aa35e14f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Southampton

9.8/10

Exceptional

(32)

"Wonderful outdoor space and great pool. Host was responsive and property was close to all things needed and wanted! Great rental for families."

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

Patricia Fox M.

[](https://www.expedia.ca/Southampton-Hotels-Delightful-Southampton-Retreat-With-Heated-Pool-Jacuzzi.h101877657.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/55000000/54250000/54242900/54242867/ec19dfea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Books](https://images.trvl-media.com/lodging/55000000/54250000/54242900/54242867/9f7825c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/55000000/54250000/54242900/54242867/de3f6f4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/55000000/54250000/54242900/54242867/930e309c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fairy Tale Guest Cottage in Magic Garden by Pool

Bridgehampton

10/10

Exceptional

(76)

"It was a beautiful cottage on a gorgeous property with gracious hosts. I recommend it!!!!"

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

Lisa

[](https://www.expedia.ca/Bridgehampton-Hotels-Fairy-Tale-Guest-Cottage-In-Magic-Garden-By-Pool.h54242867.Hotel-Information)

![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/34000000/33500000/33492900/33492827/1e7208b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/34000000/33500000/33492900/33492827/13c2a30a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33500000/33492900/33492827/19cc39dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33500000/33492900/33492827/572bf9da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready

Montauk

9.8/10

Exceptional

(107)

"Very walkable charming stay in beautiful area that supports larger group. Carter is very responsive and friendly. "

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

Kendall M.

[](https://www.expedia.ca/Montauk-Hotels-Private-Montauk-Setting-Walk-To-Beach-Town-Large-Pool-Jacuzzi-Kid-Friendly.h33492827.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

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

### The Sagaponack

10/10 Excellent

"Great place to spend a few days , clean and has everything you need for a comfortable stay ! Located great ! "

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

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

### Offshore Montauk

10/10 Excellent

"Beautifully renovated , super clean property. High quality sheets, towels, very comfortable bed. We enjoyed easy access to the beach and short distance to many dining options. Had wonderful stay and can't wait to come back."

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

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

### Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"Staff was very helpful and room was nice and clean."

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

"It was very spacious!"

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

![Greenporter Hotel](//images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/3c3df51f_y.jpg)

### Greenporter Hotel

10/10 Excellent

"Great location, great service, very clean."

[](https://expedia.ca/Greenport-Hotels-Greenporter-Hotel.h90308554.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

"We love the stay everything was perfect"

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

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

### The Atlantic Hotel

10/10 Excellent

"Great stay overall. Only suggestion would be to put a light on the side of the building. "

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

![Marram](//images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/619dc6c0_y.jpg)

### Marram

10/10 Excellent

"We came during terrible weather and couldn’t enjoy the amenities but the view and overall property is beautiful. Johnny at the front desk was very friendly and helpful. "

[](https://expedia.ca/Montauk-Hotels-Marram.h15408228.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

"Beautiful property, we loved our room, friendly staff. "

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

## Find out more about Shelter Island

**Everything you need to know about** **Shelter Island** **vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Shelter Island vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Shelter Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Shelter Island vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Shelter Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Shelter Island vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Shelter Island vacation rentals we have selected for you start as low as CA $231 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Shelter Island rentals**

At Expedia, we put the best Shelter Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Shelter Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Shelter Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Shelter Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

## Explore a world of travel with Expedia

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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)
-   [Villas in Shelter Island](https://expedia.ca/Shelter-Island-Villas.d157359-aaVillas.Travel-Guide-Accommodation)
-   [B&B in Shelter Island](https://expedia.ca/Shelter-Island-Bed-And-Breakfast.d157359-aaBedAndBreakfast.Travel-Guide-Accommodation)
-   [Motels in Shelter Island](https://expedia.ca/Shelter-Island-Motels.d157359-aaMotels.Travel-Guide-Accommodation)
-   [Farmstay in Shelter Island](https://expedia.ca/Shelter-Island-Agritourism.d157359-aaAgritourism.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)
-   [Aparthotels in Shelter Island](https://expedia.ca/Shelter-Island-Apart-Hotels.d157359-aaApartHotels.Travel-Guide-Accommodation)
-   [Guest Houses in Shelter Island](https://expedia.ca/Shelter-Island-Guest-Houses.d157359-aaGuestHouses.Travel-Guide-Accommodation)
-   [Inns in Shelter Island](https://expedia.ca/Shelter-Island-Inns.d157359-aaInns.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)
-   [Condo Resorts in Shelter Island](https://expedia.ca/Shelter-Island-Condominium-Resort.d157359-aaCondominiumResort.Travel-Guide-Accommodation)
-   [Hostels in Shelter Island](https://expedia.ca/Shelter-Island-Hostels.d157359-aaHostels.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?

> Yes, we have vacation rentals in Shelter Island close to Shelter Island Whale's Tail, or you can select a more secluded option if you'd like a relaxing place to stay. Shelter Island is known for its parks and beaches. Make sure you have time to check out the museums while you're in the area.

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

> [Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor](https://www.expedia.ca/Bridgehampton-Hotels-Cozy-Bungalow-Available-Nearby-Bridgehampton-And-Sag-Harbor.h105953994.Hotel-Information) : This vacation home rental near Shelter Island offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a patio, a garden, and a hot tub so you can immerse yourself in your vacation.

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

> Choose from 85 Expedia vacation rentals in Shelter Island for a memorable vacation.

### What can I see and do in Shelter Island?

> Sunset Beach and Crescent Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Shelter Island Whale's Tail. Mashomack Preserve and Gardiner's Bay Country Club are other places to visit while you're in town.

### What are vacation rentals like in Shelter Island?

> Vacation rentals are private properties you can reserve for a couple days or more in Shelter Island. Vacation rentals offer extras such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for family trips.

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Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app

![QR code to download the app](data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAyAAAAMgAQAAAADzCzvFAAAFP0lEQVR4Xu3cPXIbORBAYagcMNwjzFF0NMzR5ig8gkMGKsHqH6AxI0jlDrwB9V6iURPAxwykvLWl/Q+V6+BfBJIKJBVIKpBUIKlAUoGkAkkFkgokFUgqkFQgqUBSgaQCSQWSCiQVSCqQVCCpQFKBpAJJBZIKJBVIKpBUE/JWLm0yqvbiUW7y4y7z2n7bgo+RLx2jyDdKIBrIHEgfjUA0kDmQPho9K1LjtybIR/vH+hdBPnKklP9sycNGv+T5t6wanc8C0UAiEA0EpIGA+Avz7b3JdEam+on+q2yMVRuIzUcgIBIISAEB6YvicYHMoyIXuq+K/K00EBAQkL4oHkHsAQQkiczp92ld5V+xD1l1/ooNMgJpICAgICB/jUSO7Lbv9YScv2IHMgIBaSAg1xdALBCQdkXObbZWt+uF/v3oUo2TQRajSzVOBlmMLtU4GWQxulTjZJDF6FKNk0EWo0s1TgZZjC7VOHlC1u22Zb7jB1JkdLc7/rtAQNaBzIGArAOZe14ktvvtPbrJy3d71r9wN3MXI38rIxANBAQERH6AgLQT4i+8ny/0ZXriIU9jo747zd+dnNUn8QgCAqKBXAMB6Rt/IuLb7ZXT2qPcZFTs+7Sf+JDBJk970X9zHqsKCAgICAiIvwLyLfJ1eu1rd9se/5osw3grXwQC8nUgPRCQrwPpPSXia/uJfsfLta+jxzjRR8Uu9M1267Wvd/x4KyMQEBDbDQICAmKdEdk+pyPNkbt8xd5LfJ+eVr3Is68qICAgICCxCgREfq1xzGdEb29tk1G129u366rraO4xdtcYgoCAnAIBiSEISLPbu9favT++yIWubX3lu1/70i8ZuLsMBKSBgBSQZSAgfsdrun2Tp30aiRsnnl1HdJV/EhiBgIDYyyCbPIGAgFyQ2tdqeqIg73LYrc3/5qz5iU1W6ScBf3da9ZcaCAiIBQICAtI7IyM9sRii2w+bKzK/FRlp80ir/qtM4hHEHkBArOq/yiQeQewBBMSq/qtM4vHpEF3rt7eO9I5/1cV2olz7zV3b2jvk3fmHgymQBgISgYDMgbQfj2h+VT/kgE2edqNf5dlHkrrnVfHu7jKvfSkIiAcCAgIC4p0Rub37dlmrV3W48iOu/VJuMtATZaSpq1UbSCAgDQQEBASk2kCakDd7Qbdrm0zFjdTdS1zovsrfyiEuyAhkBGKvgGwyBQFpIBPSxvZDFp1P1JHko+KfBMbIPxxod5nWOBakgICAFBDtLtMax4KUH4/oHT9f1ZvNddTkxLF0/h9L64lz/u6mQOYTL4HID5AGAgLyY5FFb9cDtj6Kt6JVW3/0dTGSQEAWgUwjCQRkEcg0kp4SWZzYxlfsccfrKv+jd4zGh4Oo2hoJRAOZ22S6FxBbI4FoIHObTPcCYmukZ0Vq/NYE8VH/2/V5u97xUmxcjCSQtjxxMZJA2vLExUgCacsTFyMJpC1PXIwkkLY8cTGSQNryxMVIuiL+t+vbQCS942VxjPoq33geffMXbpDPIxBbDBKPIJ9HILYYJB6fGmnyFVu/Tx8y9e17UddHvlE7OlLGSAIBAQEBAQH5e8S396/YY3usGq7+59XXjR4ICAgIyHWjBwJyfkHXNtnuF7pu1+ZVZ/e1PcYngSmQCEQDAQHpgUQ/GDm32dy3a3d7Rb91NznRq00/CWjDHYFoIHObzUFsjQSigcxtNgexNdJTIv8ukFQgqUBSgaQCSQWSCiQVSCqQVCCpQFKBpAJJBZIKJBVIKpBUIKlAUoGkAkkFkgokFUgqkFQgqUBSgaR6HuQPqMqUlFy/Ak0AAAAASUVORK5CYII=)