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Shelter Island Holiday Rentals

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Check prices for these dates

Tonight
17 Sept - 18 Sept
Tomorrow
18 Sept - 19 Sept
This weekend
19 Sept - 21 Sept
Next weekend
26 Sept - 28 Sept

Holiday Rentals in Shelter Island

Our top choices for Shelter Island holiday rentals

Montauk Manor
Front of property – evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1248)
"Clean spacious room. Friendly staff. Excellent onsite restaurant "
The price is S$727
includes taxes & fees
12 Oct - 13 Oct
Montauk Manor
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 S$254
includes taxes & fees
29 Sept - 30 Sept
Montauk Oceanside Suites
Windward Shores Ocean Resort
Living area

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (293)
"Very nice & affordable "
The price is S$220
includes taxes & fees
13 Oct - 14 Oct
Windward Shores Ocean Resort
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 S$463
includes taxes & fees
1 Oct - 2 Oct
The Surf Club
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 S$539
includes taxes & fees
6 Oct - 7 Oct
Cliffside Resort Condominiums
Driftwood Resort
Private kitchen

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (231)
"Great place to stay for small family "
The price is S$264
includes taxes & fees
12 Oct - 13 Oct
Driftwood Resort
Offshore Residences
Living area

Offshore Residences

4.0 star property
The price is S$1,179
includes taxes & fees
1 Oct - 2 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

The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"Loved it"
Pelinsu 2-night trip
Posted 2 days ago
The Atlantic Hotel

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.