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
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Shelter Island Heights vacation rentals

Condo | Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (274 reviews)
"Comfortable and clean, and the beach location is amazing. The sunset was spectacular. We will definitely come back again!"
United States
Suzanne
$501 nightly
The price is $572
Jul 29 - Jul 30
Total with taxes and fees
Cliffside Resort Condominiums
Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (34 reviews)
"Great stay & great staff!"
United States
James
$372 nightly
The price is $425
Jul 28 - Jul 29
Total with taxes and fees
North Fork Resort
Iron/ironing board, WiFi (free), individually decorated

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
$419 nightly
The price is $479
Jul 23 - Jul 24
Total with taxes and fees
Windward Shores Ocean Resort
Apartment | WiFi (free), individually decorated, individually furnished, 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
$650 nightly
The price is $742
Jul 26 - Jul 27
Total with taxes and fees
Driftwood Resort
Premium Apartment, 1 Bedroom, Ocean View | Living area

Atlantic Bluffs Club

Atlantic Bluffs Club
3.0 star property
Montauk
$10,024 nightly
The price is $11,449
Jul 31 - Aug 1
Total with taxes and fees
Atlantic Bluffs Club
Lobby

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,371 reviews)
"Property and room very clean Friendly staff and plenty of parking"
United States
Amelia
$481 nightly
The price is $549
Aug 5 - Aug 6
Total with taxes and fees
Montauk Manor
Cottage (3 Bedrooms) | Interior

Hamptons Vacation Rental w/ Saltwater Pool

Hamptons Vacation Rental w/ Saltwater Pool
3.0 star property
Hampton Bays
$1,495 nightly
The price is $1,708
Aug 5 - Aug 6
Total with taxes and fees
Hamptons Vacation Rental w/ Saltwater Pool
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
$1,018 nightly
The price is $1,163
Aug 18 - Aug 19
Total with taxes and fees
Offshore Spa & Residences
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
$900 nightly
The price is $1,028
Aug 13 - Aug 14
Total with taxes and fees
The Surf Club
Apartment | Iron/ironing board, WiFi (free)

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (435 reviews)
"The location is amazing, and the customer service is excellent. Unfortunately, the mattress and the air conditioning were the worst I’ve ever experienced, which made my stay much less comfortable."
United States
Carlos
$412 nightly
The price is $471
Aug 10 - Aug 11
Total with taxes and fees
Montauk Oceanside Suites
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

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"The only thing negative was my wife's fish and chips at dinner. The fish had an ammonia taste but the server graciously removed it from the bill. The Resort and amenities were top notch. I will definitely stay again in the future"
William 1-night trip
Posted 11 hours ago
Saybrook Point Resort & Marina

Find out more about Shelter Island Heights

Everything you need to know about Shelter Island Heights 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 Heights 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 Heights vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Shelter Island Heights vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shelter Island Heights. 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 Heights 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 $238 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 Heights rentals

At Expedia, we put the best Shelter Island Heights 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 Heights 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 Heights 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 Heights. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

The Hampton Sack a cheerful relaxing beach cottage: Visitors like this Shelter Island Heights vacation home rental. It 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 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.