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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sep - 20 Sep

Our top choices for Shelter Island holiday rentals

Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (19 reviews)
"Great stay & great staff!"
United States
James
The price is ฿9,671
฿11,049 total
includes taxes & fees
17 Jun - 18 Jun
North Fork Resort
Condo | Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (253 reviews)
"Beautiful property- we would definitely stay there again"
United States
Allison
The price is ฿6,334
฿8,651 total
includes taxes & fees
31 May - 1 Jun
Cliffside Resort Condominiums
Lobby

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,354 reviews)
"Had a wonderful stay"
United States
Meghan
The price is ฿11,869
฿14,198 total
includes taxes & fees
21 Jun - 22 Jun
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, (240 reviews)
"Very close to beach"
United States
Rabia
The price is ฿6,180
฿8,124 total
includes taxes & fees
2 Jun - 3 Jun
Driftwood Resort
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

Ocean Surf Resort

Ocean Surf Resort

2/10 Terrible
"Sketchy. The room was clean & beautiful view. BUT, no one was on-staff to check me in when I arrived around 7pm. Keys were left in mailbox, ok. Not the worst part. Only 1 car there other than me when I arrived. Door only had a chain lock, no peephole to hallway, sliding door to ocean balcony didn’t lock & was only “secured” by a thin 1”w x .25” d piece of wood. 1 guy pulled up & sat in his vehicle for hours at night & best part, I found a CAMERA IN THE AC UNIT!!!! Definitely unsafe for females!!! Non-refundable of course so they can keep my $440 but I did not stay there. Went back the next night just to check & that same guy was in his car again! I paid for another hotel! BEWARE! Just a heads up."
Michelle 2-night trip
Posted 4 hours ago
Ocean Surf Resort

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 holiday rentals in Shelter Island?

Yes, there are holiday rentals in Shelter Island close to Shelter Island Whale's Tail, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals are there in Shelter Island?

Choose from 90 Expedia holiday rentals in Shelter Island for a memorable holiday.

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 holiday rentals like in Shelter Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Shelter Island. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for a small group gathering.