Shelter Island Heights Vacation Rentals

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Our top choices for Shelter Island Heights vacation rentals

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (314 reviews)
"We always stay at the Windward Shores when we go to Montauk. It is a beautiful, clean and comfortable place, and the price is great!"
United States
Joseph
The price is CA $331
CA $416 total
includes taxes & fees
Jun 9 - Jun 10
Windward Shores Ocean Resort

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,356 reviews)
"Had a wonderful stay"
United States
Meghan
The price is CA $528
CA $630 total
includes taxes & fees
Jun 28 - Jun 29
Montauk Manor

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (426 reviews)
"Awesome room!!! Wish I could come back in the summer"
United States
Nicki
The price is CA $299
CA $357 total
includes taxes & fees
Jun 22 - Jun 23
Montauk Oceanside Suites

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (20 reviews)
"Great stay & great staff!"
United States
James
The price is CA $380
CA $434 total
includes taxes & fees
Jun 7 - Jun 8
North Fork Resort

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (254 reviews)
"Beautiful property- we would definitely stay there again"
United States
Allison
The price is CA $311
CA $416 total
includes taxes & fees
Jun 23 - Jun 24
Cliffside Resort Condominiums

The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (282 reviews)
"Quiet, relaxing place to stay, great access to the beach and town!"
United States
Erica
The price is CA $390
CA $521 total
includes taxes & fees
Jun 10 - Jun 11
The Surf Club

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (240 reviews)
"Very close to beach"
United States
Rabia
The price is CA $341
CA $435 total
includes taxes & fees
Jun 7 - Jun 8
Driftwood Resort

Offshore Spa & Residences

Offshore Spa & Residences
4.5 star property
Downtown Montauk
10.0 out of 10, Exceptional, (1 review)
The price is CA $915
CA $1,205 total
includes taxes & fees
Jun 23 - Jun 24
Offshore Spa & Residences

Atlantic Bluffs Club

Atlantic Bluffs Club
3.0 star property
Montauk
Atlantic Bluffs Club
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 Heights Hotel Reviews

Find out more about Shelter Island Heights

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Shelter Island Heights. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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Frequently asked questions

Are there vacation rentals in Shelter Island Heights?

Yes, you can find vacation rentals close to the most popular attractions in Shelter Island Heights, or you can select a more remote option if you'd like a relaxing place to stay. Nature enthusiasts will enjoy the beaches in Shelter Island Heights. Make sure you have time to check out the golf courses and entertainment choices during your trip.

What's the top vacation rental that Shelter Island Heights has to offer?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : You might want to consider this vacation rental near Shelter Island Heights, which is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a patio and a garden.

How many vacation rentals are there in Shelter Island Heights?

With 30 Expedia vacation rentals, you're sure to find just the right place for your Shelter Island Heights stay.

What’s there to see and do in Shelter Island Heights?

Sunset Beach and Crescent Beach are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Shelter Island Country Club and Sylvester Manor.

What’s a vacation rental in Shelter Island Heights like?

Vacation rentals are privately owned properties where you can stay for a long or short time in Shelter Island Heights. Vacation rentals feature amenities such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family getaway.