Shelter Island Holiday Rentals from NZ$323: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Shelter Island has to offer?

Hamptons Retreat : This holiday home rental outside of Shelter Island offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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Holiday Rentals in Shelter Island

Enjoy cooking in this kitchen with a central island, herringbone tile backsplash, and stainless steel appliances.

"Open concept home beautiful with private yard space. It was perfect for our stay"

includes taxes & fees

15 July - 16 July

Relax in this spacious living space with a large sofa, comfortable bench, and flat-screen TV.

includes taxes & fees

15 July - 16 July

Relax by the serene pool surrounded by tall trees and a well-maintained lawn.

"Great place! Great communication with property owner!"

includes taxes & fees

15 July - 16 July

Enjoy cooking in this well-equipped kitchen with sleek cabinetry, a wooden countertop, and stainless steel appliances.

"Everything was great!"

includes taxes & fees

23 July - 24 July

Stroll through the lush garden, surrounded by tall trees and vibrant greenery, and enjoy a meal at the covered grill.

"My family and I came for an 8 day event from a different state and wanted a clean and comfortable place to stay with our at the time 9 month old daughter. And this place did exactly that. Comfortable and CLEAN. The owner did a great job with details. Even when we had unexpected check out delays the owner showed human empathy. Great place!"

includes taxes & fees

16 July - 17 July

Relax in this serene room with a large bed, nightstand, and stunning water view.

includes taxes & fees

17 July - 18 July

Relax in a serene space with a sofa, armchair, and floor lamp, offering a view of lush greenery through large windows.

includes taxes & fees

15 July - 16 July

Enjoy a peaceful evening by the water with a fire pit and serene views of the surrounding area.

"We stayed at this wonderful property for 3 nights and it had everything we were looking and more! Looking forward to our next visit!"

includes taxes & fees

20 July - 21 July

Relax in this serene bedroom with a large bed, chandelier, and window offering a view of lush greenery.

"We had a fantastic stay! The home was exactly as described — clean and very comfortable. The location was perfect. We loved being close to town. Communication was smooth and easy — Frank was quick to respond. We’d absolutely stay here again and recommend it to anyone visiting the area! "

includes taxes & fees

5 Aug - 6 Aug

Enjoy a serene beach experience with a pebbly shore and a wooden pier extending into the water.

includes taxes & fees

18 July - 19 July

"Nicely decorated house. Close to Mystic, Mohegan Sun and multiple beaches and state parks. My son loved the house as well. Very accommodating and had a lot of things that were helpful (beach chairs, bikes, blankets, shades/curtains, suggestions on where to eat). Overall a great place to stay!"

includes taxes & fees

24 July - 25 July

Enjoy the outdoor space with a swimming pool, hot tub, and deck seating.

"Great location and amenities. "

includes taxes & fees

22 July - 23 July

Enjoy breathtaking sea views from this balcony with wicker chairs and a potted plant.

"Beautiful sunrise, sunsets and scenery. Beautiful property"

includes taxes & fees

29 July - 30 July

Stroll up to this charming colonial-style house, featuring a welcoming front porch with a bench and a beautiful garden.

"So the listing said house number 26 but it's really 25. So we circled the block a few times. Then the key was not in the key safe. Called the owner who apologized profusely. Had to wait a half hour for the key. Not ideal. Otherwise ok. "

includes taxes & fees

15 July - 16 July

Prepare meals in the central island kitchen with a stove and ample counter space, offering a view of the outdoors.

includes taxes & fees

2 Aug - 3 Aug

Enjoy ocean views from the large windows in this room, which features a dining table and comfortable seating.

"We came for a girls trip and this property was perfect, had beautiful views and was close to everything...we very much enjoyed our stay!"

includes taxes & fees

27 July - 28 July

Enjoy cooking in this well-equipped kitchen with a large island, bar stools, and stainless steel appliances.

"good times"

includes taxes & fees

15 July - 16 July

Relax on the deck with a clear view of the water, featuring lounge chairs and a picnic table.

"Quick stay after a day at the wineries. Location is is set in a beautiful quiet area and the view is just amazing. The staff could truly not be any better, any request or issue was dealt with in literally a minute. Room was perfect, clean and made you feel at home with anything you needed. Will definitely be back!"

includes taxes & fees

28 July - 29 July

"The property was exactly as posted. The host was great, super helpful and responsive. The pool was awesome for the kids. It was private and a wonderful stay in Sag Harbor. The town was cute and close. We would definitely stay again ! Thanks so much!"

includes taxes & fees

20 July - 21 July

Walk along the beach on a paved path, bordered by grass and rocky shoreline, with the ocean stretching out to the horizon.

"Close to the shore and the heart of Old Saybrook. The house is very comfortable."

includes taxes & fees

2 Aug - 3 Aug

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Find out more about Shelter Island

Everything you need to know about Shelter Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Shelter Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Shelter Island holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Shelter Island holiday rentals we have selected for you start as low as NZ$323 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 holiday 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 holiday.

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.

Recent reviews of Shelter Island properties

5/5 Excellent

"Brand new, clean and friendly hotel. Would 1000% come back."

A verified traveller stayed at Offshore Montauk

Posted 2 days ago

5/5 Excellent

"Right on the water. Private beach with chair and umbrellas.they will serve you right on the beach bye getting you food and drinks also has a outdoor swimming pool..nice staff..nothing special about the continental breakfast..bagels, fruit, small croissants, small danish and some hard boiled eggs..coffee and oj..i was pleased with my stay. King deluxe room..small table with chairs on the shared deck..could sit outside til about 2pm and the sun starts to beat on you but no biggy..was very humid out when my wife and i was there..a/ c really could not cool the room as much as we would have liked. Nothing wrong with the a/c it just because the sun beating on the hotel all day..luckily i brought a couple of small usb fans to help keep cool at night while we slept did the trick..overall i enjoy my stay and you could not ask for anything more when it comes to the scenery.. "

A verified traveller stayed at Sound View Greenport

Posted 3 days ago

5/5 Excellent

Excellent Place to Stay!!!...5 Stars & More!!

"We stayed 5 days! Customer service was great ;) Housekeeping was great, the cafe in the morning was excellent! Lounge area if you wanted to go out in the evening they had Pool, Darts, & Karaoke If you didn't want to go to the Beach, they had a Pool/Gym Right near the Highway & Route 1 We had a wonderful Stay!!...Will definitely go back!!! Gave them 5 Stars ;)"

A verified traveller stayed at Quality Inn Old Saybrook - Westbrook

Posted 3 days ago

5/5 Excellent

"We loved our stay at Marram! The property is a little slice of beach magic. The location was absolutely perfect, and the private beach was exactly what we were hoping for. Tranquil and beautiful, they have effortlessly blended luxury into the unpretentious surf town vibes that Montauk is known for. The staff is attentive, friendly, and helpful. The common areas were family friendly and we loved the fire pits, covered patio deck, and lounge area. Our beds were insanely comfortable and the room decor simple and elegant. A few things could have improved our stay: Our room had very limited storage, so with no closet to stow things away the minimalist aesthetic quickly went out the window. Our room had the sink/vanity area outside the bathroom, and only the shower and toilet inside. This was awkward for us to navigate as a family. We loved the smell of the Le Labo bath products, but I am always hesitant to use communal products in hotels as you never know if it has been tampered with. I would have preferred individually sized recyclable bottles to enjoy that amenity. Overall, we adored it and would recommend it 10/10! "

A verified traveller stayed at Marram

Posted 3 days ago

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Frequently asked questions

Can I find holiday rentals in Shelter Island?

Yes, there are holiday rentals in Shelter Island close to Shelter Island Whale's Tail, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Shelter Island has to offer?

Hamptons Retreat: This holiday home rental outside of Shelter Island offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Shelter Island?

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

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 Shell Beach are other places to visit while you're in town.

What are holiday rentals like in Shelter Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Shelter Island. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for a small group gathering.

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Shelter Island Holiday Rentals

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Holiday Rentals in Shelter Island

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Stunning Southampton Village Modern Home

Stunning Southampton Village Modern Home

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic

Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA

Sag Harbor Water View w Dock

Sag Harbor Water View w Dock

Charming 1-bedroom private suite in exclusive neighborhood house in Amagansett

Charming 1-bedroom private suite in exclusive neighborhood house in Amagansett

2BED GUESTHOUSE WITH PRIVATE BEACH ACCESS

2BED GUESTHOUSE WITH PRIVATE BEACH ACCESS

Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi

Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi

Spacious 5-bedroom house with water views and 2 houses from the bay.

Spacious 5-bedroom house with water views and 2 houses from the bay.

Cheerful 3bd Cape yards from beach/ river access

Cheerful 3bd Cape yards from beach/ river access

Stylish Modern Retreat in the Heart of the Hamptons: Your Perfect Getaway!

Stylish Modern Retreat in the Heart of the Hamptons: Your Perfect Getaway!

Private beach on a fenced in property sunset views

Private beach on a fenced in property sunset views

Shoreline Oasis

Shoreline Oasis

east hampton getaway

east hampton getaway

Gorgeous Greenport Beach House right on the Sound! Breathtaking views

Gorgeous Greenport Beach House right on the Sound! Breathtaking views

Cozy quiet gem, private & fenced in backyard

Cozy quiet gem, private & fenced in backyard

Aqua by American Beech - Rooftop Suite

Aqua by American Beech - Rooftop Suite

Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach

Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach

adorable ranch in beach community

adorable ranch in beach community

Find out more about Shelter Island

Find out more about Shelter Island

Recent reviews of Shelter Island properties

Recent reviews of Shelter Island properties

Offshore Montauk

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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Frequently asked questions