Shelter Island Vacation Rentals from $222: Search Short-Term Rentals

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

The Hampton Sack a cheerful relaxing beach cottage : This vacation home rental near Shelter Island is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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In two weeks

In two months

In three months

In four months

Our top choices for Shelter Island vacation rentals

1. Cliffside Resort Condominiums

Greenport

Christine

$385 nightly

Sep 7 - Sep 8

Total with taxes and fees

2. North Fork Resort

Greenport

Lisa

$275 nightly

Sep 13 - Sep 14

Total with taxes and fees

3. Windward Shores Ocean Resort

Napeague

Gaurang J

$249 nightly

Sep 20 - Sep 21

Total with taxes and fees

4. Driftwood Resort

Montauk

William

$195 nightly

Sep 20 - Sep 21

Total with taxes and fees

5. Montauk Manor

Montauk

Amelia

$314 nightly

Sep 7 - Sep 8

Total with taxes and fees

6. Montauk Oceanside Suites

Downtown Montauk

christopher

$214 nightly

Sep 8 - Sep 9

Total with taxes and fees

7. The Surf Club

Montauk

Anna

$359 nightly

Sep 9 - Sep 10

Total with taxes and fees

One Bedroom Residence King with Ocean View | Living area

8. Offshore Spa & Residences

Downtown Montauk

"What a memorable way to celebrate America’s 250th Anniversary and the Fourth of July at Offshore Montauk. The festive atmosphere, beautiful weather, beach days, and fireworks made for an unforgettable getaway. The property is beautifully designed with thoughtful room layouts, high-end appliances, and quality finishes that create a luxurious yet comfortable experience. The attention to detail throughout the property is impressive, and it's exciting to see the continued improvements being...

Frank

$932 nightly

Sep 20 - Sep 21

Total with taxes and fees

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Top Shelter Island Hotel Reviews

Montauk Blue Hotel

10/10 Excellent

"Great place to stay!! Walking distance to town. Love it!!"

The Shoals Suites and Slips

8/10 Good

"The location and the setting are great. Loved the layout of the spacious room with a little kitchenette. The bed was very comfortable and had nice linens. The whole place inside and out was very clean, and we loved walking and sitting down by the marina. The Lavazza coffee in room was delicious! We didn't get to try out the food truck, but the complimentary breakfast was underwelming. It included some rather dry pastries and coffee that needed to be refilled a couple times while I waited. The breakfast area and lobby / sitting area is beautiful so that part was enjoyable."

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"Absolute gem really cool giant picnic table in the middle of the room, which is great for kids are just getting work done. The staff is absolutely wonderful. The view is gorgeous. If you stay on the backside of the hotel cannot recommend this place enough. What a surprise incredible bargain."

Budget Host East End

8/10 Good

"We came for the pool and enjoyed every minute of a few relaxing days poolside. Lush green grounds provided some shady picnic tables when it was time to get out of the sun. If you are looking for an inexpensive stay not far from the Hamptons or North Fork this is your place. Staff, especially, front desk, very nice, friendly and informative. Rooms had a mini fridge and comfy bed. A/C worked great. Try to get a poolside room. Hotel includes continental breakfast on weekends. Multiple excellent restaurant options nearby on Main Street. We would recommend Olga's for breakfast, offers outdoor/indoor seating. For dinner there is Cliff's Rendezvous steak house. Call and go when they offer their steak special night. Jerry and the Mermaid for seafood, also has outdoor/indoor seating by the water. There is Tweed's where you can try Buffalo. And a few hidden gems with great water views and outdoor seating -Turkuaz (Turkish food ) and Country Farm Kitchen. There is Atlantis Aquarium nearby, that also offers boat tours of the Peconic by day and booze cruises weekend eves. Suffolk Theatre offers well known artists in concert on the weekends. There are at least 4 breweries a short drive away and homemade ice cream at Snowflake and homemade chocolate at North Fork Chocolate & Eatery. Polish Town is nearby if you want Polish food try the Birchwood Restaurant or groceries from the town's deli's."

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Shelter Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $222 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

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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?

The Hampton Sack a cheerful relaxing beach cottage: This vacation home rental near Shelter Island is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Shelter Island?

Choose from 90 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. Shelter Island Historical Society and Mashomack Preserve 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.

Room 1

Check prices for these dates

Our top choices for Shelter Island vacation rentals

1. Cliffside Resort Condominiums

2. North Fork Resort

3. Windward Shores Ocean Resort

4. Driftwood Resort

5. Montauk Manor

6. Montauk Oceanside Suites

7. The Surf Club

8. Offshore Spa & Residences

Find vacation rentals that suit your style

Top Shelter Island Hotel Reviews

Montauk Blue Hotel

The Shoals Suites and Slips

Sound View Greenport

Hampton's Vacation Inn

Pier Blue Inn Old Saybrook - Essex

Zey Hotel

Offshore Montauk

Budget Host East End

North Fork Resort

Find out more about Shelter Island

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Frequently asked questions

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