Shelter Island Vacation Rentals from CA $104: Short-Term Rentals for 2025

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

Hamptons Retreat : 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. It has 4 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 balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

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Vacation Rentals in Shelter Island

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

"good times"

CA $1,602 total

includes taxes & fees

Jul 15 - Jul 16

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"

CA $634 total

includes taxes & fees

Jul 14 - Jul 15

Relax by the pool surrounded by lush greenery and flowering plants.

"We loved the simple « ranch » layout with an architectural twist and the beautiful swimming pool And we really appreciated all the little attentions and touches that made our stay feel like a real vacation! Thank you Dorothy!"

CA $2,921 total

includes taxes & fees

Aug 4 - Aug 5

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

"Great location and amenities. "

CA $4,778 total

includes taxes & fees

Jul 22 - Jul 23

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

CA $2,725 total

includes taxes & fees

Aug 2 - Aug 3

"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!"

CA $1,310 total

includes taxes & fees

Jul 24 - Jul 25

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!"

CA $824 total

includes taxes & fees

Jul 20 - Jul 21

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! "

CA $984 total

includes taxes & fees

Aug 5 - Aug 6

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

"Great place! Great communication with property owner!"

CA $716 total

includes taxes & fees

Jul 15 - Jul 16

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

CA $9,259 total

includes taxes & fees

Jul 17 - Jul 18

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

CA $8,535 total

includes taxes & fees

Jul 17 - Jul 18

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

"Everything was great!"

CA $554 total

includes taxes & fees

Jul 14 - Jul 15

"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!"

CA $1,677 total

includes taxes & fees

Jul 20 - Jul 21

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

CA $22,715 total

includes taxes & fees

Jul 14 - Jul 15

Relax by the pool surrounded by lush greenery and trees, perfect for a family-friendly outdoor retreat.

"Great location and comfortable home. Easy check in and check out."

CA $3,601 total

includes taxes & fees

Aug 1 - Aug 2

Relax in this stylish living area with a sofa, armchair, and coffee table, surrounded by a large window offering a view of the outdoors.

"Second year at this lovely house for the 4th of July extended weekend. The hosts are responsive and helpful, and the house is exactly what you need for 2-3 people. Very clean, nicely decorated, kitchen was nicely stocked. It is in a great location. Easily able to walk into town for shopping or dining."

CA $1,597 total

includes taxes & fees

Jul 27 - Jul 28

Cozy up by the fireplace, surrounded by abstract art and lush views.

"Great location, clean, easy checkin, slept 7 comfortably"

CA $2,619 total

includes taxes & fees

Jul 14 - Jul 15

Enjoy cooking in this well-lit kitchen with a central island and stainless steel range hood.

CA $2,002 total

includes taxes & fees

Jul 14 - Jul 15

Enjoy dining al fresco in a serene outdoor setting with lush greenery and ambient lighting.

"We thoroughly enjoyed our stay!"

CA $544 total

includes taxes & fees

Jul 14 - Jul 15

Relax in this inviting outdoor seating area with a sofa, wicker chair, and fire feature.

"Excellent one night stay."

CA $594 total

includes taxes & fees

Aug 4 - Aug 5

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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, 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 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 $104 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.

Recent reviews of Shelter Island properties

5/5 Excellent

"Great experience! Very clean felt upscale ! Staff was great! "

A verified traveller stayed at Offshore Montauk

Posted 1 day 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 2 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

5/5 Excellent

"Took a chance on a last minute two night family getaway and I am so glad we did. Check in could not have been faster and kinder, shout out to Daren you are a treasure of a human! It’s a really cute, updated motel/hotel, the grounds are beautiful and clean as are the rooms. Compared to other places like this, this was absolutely more spacious and had more amenities. Deck, and sand area were great to hangout on, we played some games and had a blast. Day one we hung around at the pool and did the generous $10 beach pass from the Bayview the 2nd day and spent a great day at the beach. You need a car here in order to go to local resturants, coffee places (although there is morning coffee in the communal lounge and a coffee maker in the room) Mini fridge and microwave was a huge help with young kids. They really make this place easy to be a guest at, are happy to give extra towels and everyone was super friendly. If anyone is complaining here I would not understand why. We will be back!"

A verified traveller stayed at Bayview Resort

Posted 4 days ago

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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?

Hamptons Retreat: 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. It has 4 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 balcony, a garden, and a selection of games 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 Shell Beach 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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Shelter Island Vacation Rentals

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Vacation Rentals in Shelter Island

Cozy quiet gem, private & fenced in backyard

Cozy quiet gem, private & fenced in backyard

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

East Hampton slice of heaven with heated pool and 3 minute drive to village.

East Hampton slice of heaven with heated pool and 3 minute drive to village.

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

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

east hampton getaway

east hampton getaway

Cheerful 3bd Cape yards from beach/ river access

Cheerful 3bd Cape yards from beach/ river access

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

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Sag Harbor Water View w Dock

Sag Harbor Water View w Dock

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.

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic

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

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

Stunning Southampton Village Modern Home

Stunning Southampton Village Modern Home

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Village gem walk to Main Street fenced in property

Village gem walk to Main Street fenced in property

Charming Village home in the heart of Southampton

Charming Village home in the heart of Southampton

Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7

American Beech - King Suite 2

American Beech - King Suite 2

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

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Explore a world of travel with Expedia

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