Shelter Island Vacation Rentals

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Check prices for these dates

In two weeks
Dec 5 - Dec 7
In two months
Jan 16 - Jan 18
In three months
Feb 13 - Feb 15
In four months
Mar 13 - Mar 15

Vacation Rentals in Shelter Island

Front of property - evening/night
Montauk Manor

Montauk Manor

3.5 star property
Montauk
9.2 out of 10, Wonderful, (1262)
"Always excellent, even suring my eleventh stay."
United States
Daryl
The price is NT$4,320
NT$5,545 total
includes taxes & fees
Dec 1 - Dec 2
Montauk Manor
Beach nearby
Cliffside Resort Condominiums

Cliffside Resort Condominiums

3.0 star property
Greenport
9.0 out of 10, Wonderful, (248)
"Great stay - beautiful place"
United States
Rebecca
Cliffside Resort Condominiums
Apartment | Private kitchen | Fridge, microwave, stovetop
Montauk Oceanside Suites

Montauk Oceanside Suites

3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (417)
"We loved it, suite size was great! "
United States
Patrick
Montauk Oceanside Suites
Apartment, 1 Bedroom | Private kitchen | Fridge, microwave, cookware/dishes/utensils
Driftwood Resort

Driftwood Resort

3.5 star property
Montauk
9.0 out of 10, Wonderful, (236)
"Great place to stay for small family "
United States
DongHo
Driftwood Resort
One Bedroom Condo King with Ocean view | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu
Offshore Residences

Offshore Residences

4.5 star property
Downtown Montauk
The price is NT$14,929
NT$20,617 total
includes taxes & fees
Nov 30 - Dec 1
Offshore Residences
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 Hotel Reviews

The Sagaponack

The Sagaponack

10/10 Excellent
"Beautiful room, loved the treats at the galley."
Andrew 1-night trip
Posted 15 hours ago
The Sagaponack

Find out more about Shelter Island

Search for holiday rentals in Shelter Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Shelter Island using one of the methods below:

  • View our selection of featured holiday rentals in Shelter Island
  • Use the map to find apartments and other holiday homes in the Shelter Island neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Shelter Island while they last

Look no further and take a look at our great range of rental properties in Shelter Island!

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.

How many vacation rentals are there in Shelter Island?

Choose from 84 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.