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Shelter Island Vacation Rentals

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Check prices for these dates

In two weeks
10 Oct - 12 Oct
In one month
24 Oct - 26 Oct
In two months
21 Nov - 23 Nov
In three months
19 Dec - 21 Dec

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 RM1,178
RM1,428 total
includes taxes & fees
23 Oct - 24 Oct
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 RM553
RM724 total
includes taxes & fees
15 Oct - 16 Oct
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 RM571
RM699 total
includes taxes & fees
20 Oct - 21 Oct
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 RM1,303
RM1,671 total
includes taxes & fees
2 Oct - 3 Oct
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 RM940
RM1,302 total
includes taxes & fees
25 Sept - 26 Sept
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 RM581
RM800 total
includes taxes & fees
29 Sept - 30 Sept
Driftwood Resort
Offshore Residences
Living area

Offshore Residences

4.0 star property
The price is RM2,221
RM3,018 total
includes taxes & fees
19 Oct - 20 Oct
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

Offshore Montauk

Offshore Montauk

10/10 Excellent
"Amazing hotel and location. Pet friendly and newly renovated - loved everything about the hotel and staff "
Amandip 2-night trip
Posted 11 hours ago
Offshore Montauk

Find out more about Shelter Island

Find out more about Shelter Island

Search for holiday rentals in Shelter Island on Expedia.co.uk! 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 86 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. Gardiner's Bay Country Club and Shelter Island Historical Society 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.