Title: Shelter Island Vacation Rentals from CA $229: Short-Term Rentals for 2025 | Expedia.ca

  

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# Shelter Island Vacation Rentals

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## Check prices for these dates

Tonight

[Oct 11 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-11&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-12&endDate=2025-10-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

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

## Vacation Rentals in Shelter Island

![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)

![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)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/700cd038.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Windward Shores Ocean Resort

Amagansett

8.8/10

Excellent

(296)

"Very nice & affordable "

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

![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)

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

### Montauk Manor

Montauk

9.2/10

Wonderful

(1253)

"Beautiful grounds, excellent staff"

CA $176

CA $229 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)

![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)

![Porch](https://images.trvl-media.com/lodging/12000000/11070000/11062900/11062836/026ba813.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)

### Montauk Oceanside Suites

Downtown Montauk

8.6/10

Excellent

(414)

"We loved it, suite size was great! "

CA $191

CA $233 total

includes taxes & fees

Oct 20 - Oct 21

[](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/d9295239.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/fa408cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cliffside Resort Condominiums

Greenport

9.0/10

Wonderful

(242)

"Great view of the water and nice amenities with the beach and pool."

CA $314

CA $419 total

includes taxes & fees

Nov 2 - Nov 3

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

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207128/5f3d4968.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

(278)

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

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

![Apartment](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207142/14ba9bab.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)

![Exterior](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207142/d8406ee7.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 "

CA $202

CA $276 total

includes taxes & fees

Oct 13 - Oct 14

[](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)

![On the beach](https://images.trvl-media.com/lodging/27000000/26560000/26554100/26554014/ca35c4da.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!...

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

![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101880000/101877700/101877657/67d18d47.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)

![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)

"Our trip was amazing, the pool was in perfect condition and the house had everything we needed. Would definitely stay here again!!"

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

![Interior](https://images.trvl-media.com/lodging/106000000/105960000/105954000/105953994/200490ea.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)

 

### 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! "

CA $246

CA $569 total

includes taxes & fees

Oct 15 - Oct 16

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

![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/ec09d195.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/c0b20841.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)

![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

Waterford

10/10

Exceptional

(9)

"This listing was perfect for our stay. Close to the water, beautifully styled, and plenty of items to cook and clean.Thanks so much, Erin!"

CA $210

CA $453 total

includes taxes & fees

Nov 5 - Nov 6

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

![Exterior](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/728215df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/ea540de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/38c1ca05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/1f01f033.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Shoreline Oasis

Clinton

9.2/10

Wonderful

(7)

"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"

CA $251

CA $368 total

includes taxes & fees

Oct 13 - Oct 14

[](https://www.expedia.ca/Clinton-Hotels-Shoreline-Oasis.h113308197.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104810000/104804300/104804253/69c78126.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/105000000/104810000/104804300/104804253/46ba0f9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, coffee/tea maker, electric kettle, toaster](https://images.trvl-media.com/lodging/105000000/104810000/104804300/104804253/3a51fa39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/105000000/104810000/104804300/104804253/c8232312.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!

Old Lyme

10/10

Exceptional

(15)

"Such a fun, beautiful and unique stay. Would love to stay again!"

CA $273

CA $460 total

includes taxes & fees

Oct 14 - Oct 15

[](https://www.expedia.ca/Old-Lyme-Hotels-Cozy-Houseboat-Escape-Surrounded-By-Breath-Taking-Views-Across-From-Rocky-Neck.h104804253.Hotel-Information)

![On the beach](https://images.trvl-media.com/lodging/34000000/33090000/33088400/33088314/ee3ffaa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33090000/33088400/33088314/43458864.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/34000000/33090000/33088400/33088314/eb892682.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33090000/33088400/33088314/3676e074.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!

Montauk

9.8/10

Exceptional

(96)

"Very Nice stay there for business would go back for pleasure"

[](https://www.expedia.ca/Montauk-Hotels-Newly-Renovated-Montauk-Oceanfront-Condo-Steps-To-Beach.h33088314.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/71000000/70110000/70101200/70101127/d31ec06c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/71000000/70110000/70101200/70101127/57b353a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/71000000/70110000/70101200/70101127/358a7fae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/71000000/70110000/70101200/70101127/66e0afe2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!

Westbrook Center

10/10

Exceptional

(7)

"We enjoyed our time in Westbrook! Hosts were more than accomodating and helpful throughout our stay - thank you! House is cute, the perfect size for a small group, and in a good location (walking distance to many shops and restaurants). Private beach access is easy to get to (beach area is small, but it worked!)"

[](https://www.expedia.ca/Westbrook-Hotels-Perfect-Shoreline-Stay-Walk-To-Beach.h70101127.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)

![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)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/55000000/54250000/54242900/54242867/03847a16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Bridgehampton

10/10

Exceptional

(75)

"We had an AMAZING stay at Eunyoung and Mark's magical cottage. The property was exactly as described. Eunyoung and Mark are delightful people. Tranquil, quiet, peaceful. "

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

![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)

![Property grounds](https://images.trvl-media.com/lodging/33000000/32530000/32523000/32522969/ad085255.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)

### MONTAUK MANOR-DELUXE STUDIO APARTMENT

MONTAUK

9.8/10

Exceptional

(75)

"We were so excited to come back to this property after our lovely stay in february! We had an amazing time again and loved it! "

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

![Property grounds](https://images.trvl-media.com/lodging/34000000/33570000/33561600/33561503/b05e12cd.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)

![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)

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

Hampton Bays

9.6/10

Exceptional

(140)

"Perfect property to hangout and stay entertained for hours"

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

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

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/34000000/33500000/33492900/33492827/3c58e4b5.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)

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

Montauk

9.8/10

Exceptional

(106)

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

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

![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)

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

CA $72

CA $232 total

includes taxes & fees

Oct 14 - Oct 15

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

![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/35000000/34150000/34146700/34146658/w6016h4012x0y0-a337bac6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34150000/34146700/34146658/a9e385d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/35000000/34150000/34146700/34146658/14b2be2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/35000000/34150000/34146700/34146658/3adfb5a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

East Hampton

10/10

Exceptional

(95)

"We loved our stay - it was nice to be a short walk away from the bay and the pool was great. The home was very clean and comfortable."

[](https://www.expedia.ca/East-Hampton-Hotels-Mid-Century-Holiday-Retreat-Private-Beach.h34146658.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

**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 $229 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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-   All accommodation types in Shelter Island

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-   [Québec Vacation Rentals](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

-   [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?

> [Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping](https://www.expedia.ca/Southampton-Hotels-Delightful-Southampton-Retreat-With-Heated-Pool-Jacuzzi.h101877657.Hotel-Information): This vacation home rental near Shelter Island offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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

> Choose from 86 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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Flights

-   [Cheap Flights from Ogdensburg](https://expedia.ca/lp/flights/2648/flights-from-ogdensburg)
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Activities

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General

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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,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)