A pebbled beach with a sunset and a distant bridge.

Shelter Island Heights Vacation Rentals

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sep - 6 Sep
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Shelter Island Heights vacation rentals

Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (29 reviews)
"Great stay & great staff!"
United States
James
The price is SAR 1,237
SAR 1,414 total
includes taxes & fees
8 Jul - 9 Jul
North Fork Resort
Condo | Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (266 reviews)
"Beautiful property- we would definitely stay there again"
United States
Allison
The price is SAR 1,193
SAR 1,527 total
includes taxes & fees
23 Jul - 24 Jul
Cliffside Resort Condominiums
Individually decorated, individually furnished, iron/ironing board

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (319 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 SAR 1,596
SAR 1,925 total
includes taxes & fees
8 Jul - 9 Jul
Windward Shores Ocean Resort
Lobby

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,364 reviews)
"Had a wonderful stay"
United States
Meghan
The price is SAR 1,740
SAR 2,062 total
includes taxes & fees
23 Jul - 24 Jul
Montauk Manor
Apartment | Individually decorated, individually furnished, free WiFi, bed sheets

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (242 reviews)
"Very close to beach"
United States
Rabia
The price is SAR 1,258
SAR 1,560 total
includes taxes & fees
7 Jul - 8 Jul
Driftwood Resort
Apartment | Iron/ironing board, free WiFi

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (431 reviews)
"Clean. Great location to beach and town."
United States
Cheryl
The price is SAR 1,405
SAR 1,646 total
includes taxes & fees
14 Jul - 15 Jul
Montauk Oceanside Suites
Apartment | Living area

The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (287 reviews)
"Quiet, relaxing place to stay, great access to the beach and town!"
United States
Erica
The price is SAR 1,293
SAR 1,734 total
includes taxes & fees
7 Jul - 8 Jul
The Surf Club
One Bedroom Condo King with Ocean view | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

Offshore Spa & Residences

Offshore Spa & Residences
4.5 star property
Downtown Montauk
10.0 out of 10, Exceptional, (3 reviews)
"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...
United States
Frank
The price is SAR 3,830
SAR 4,805 total
includes taxes & fees
20 Jul - 21 Jul
Offshore Spa & Residences
Premium Apartment, 1 Bedroom, Ocean View | Living area

Atlantic Bluffs Club

Atlantic Bluffs Club
3.0 star property
Montauk
The price is SAR 33,789
SAR 38,698 total
includes taxes & fees
31 Jul - 1 Aug
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

Aqualina Inn Montauk

Aqualina Inn Montauk

10/10 Excellent
"absolutely the best stay !! close to all. Cleanest can be and the staff , Amazing . I usually stay at Driftwood but wanted to try in Town. Great choice !! cant wait to book again !"
josephine 2-night trip
Posted 1 hour ago
Aqualina Inn Montauk

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?

Exquisite New Hampton Home in a Perfect Location: You might want to consider this vacation home rental near Shelter Island Heights, which is located by the ocean and has a fireplace, a balcony, and a barbecue grill to put you at ease 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. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals are there in Shelter Island Heights?

With 31 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.