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Shelter Island Vacation Rentals

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Sep 28 - Sep 29
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Vacation Rentals in Shelter Island

Montauk Manor
Front of property - evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1250)
"I had the best time and highly recommend this hotel!"
The price is P17,270
P20,869 total
includes taxes & fees
Oct 24 - Oct 25
Montauk Manor
Windward Shores Ocean Resort
Living area

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (295)
"Very nice & affordable "
The price is P7,662
P10,018 total
includes taxes & fees
Oct 19 - Oct 20
Windward Shores Ocean Resort
Montauk Oceanside Suites
Private kitchen

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (414)
"We loved it, suite size was great! "
The price is P7,913
P9,672 total
includes taxes & fees
Oct 20 - Oct 21
Montauk Oceanside Suites
Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (240)
"Great view of the water and nice amenities with the beach and pool."
The price is P15,124
P19,806 total
includes taxes & fees
Oct 5 - Oct 6
Cliffside Resort Condominiums
The Surf Club
On the beach, white sand

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (277)
"Very close walk to the beach great for little ones "
The price is P15,700
P21,099 total
includes taxes & fees
Sep 29 - Sep 30
The Surf Club
Driftwood Resort
Private kitchen

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (232)
"Great place to stay for small family "
The price is P8,039
P11,079 total
includes taxes & fees
Sep 29 - Sep 30
Driftwood Resort
Offshore Residences
Living area

Offshore Residences

4.0 star property
The price is P30,760
P41,787 total
includes taxes & fees
Oct 19 - Oct 20
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

Montauk Blue Hotel

Montauk Blue Hotel

10/10 Excellent
"Great hotel, nice staff, clean and i loved the beach access. Only downfall was the 1 bathroom when not checked intoba room. Long line and humid"
Grazyna 1-night trip
Posted 5 days ago
Montauk Blue Hotel

Find out more about Shelter Island

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 86 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. Mashomack Preserve and Gardiner's Bay Country Club 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.