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Shelter Island Vacation Rentals

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Aug 12 - Aug 13
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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, (1230)
"I had the best time and highly recommend this hotel!"
The price is P16,944
P20,475 total
includes taxes & fees
Sep 1 - Sep 2
Montauk Manor
Montauk Oceanside Suites
Private kitchen

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (404)
"great place to stay"
The price is P11,321
P13,555 total
includes taxes & fees
Sep 3 - Sep 4
Montauk Oceanside Suites
The Surf Club
On the beach, white sand

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (270)
"The front desk was great !!"
The price is P19,190
P25,027 total
includes taxes & fees
Sep 3 - Sep 4
The Surf Club
Windward Shores Ocean Resort
Living area

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (290)
"Easy checking in and out Easy access few steps to beach from first floor unit "
The price is P10,992
P13,800 total
includes taxes & fees
Sep 7 - Sep 8
Windward Shores Ocean Resort
Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (234)
"Great location, great views. Walls are a little thin."
The price is P19,303
P24,532 total
includes taxes & fees
Sep 11 - Sep 12
Cliffside Resort Condominiums
Driftwood Resort
Private kitchen

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (227)
"Phenomenal property and our room had a private sand patio. Service was extremely attentive and friendly. The beach was very spacious and pretty clean."
The price is P17,686
P22,064 total
includes taxes & fees
Sep 8 - Sep 9
Driftwood Resort
Canoe Place Waterfront Residences
Front of property

Canoe Place Waterfront Residences

4.0 star property
10.0 out of 10, Exceptional, (1)
Canoe Place Waterfront 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
"Super charming and clean and the beach is right there. Couldn't ask for more!"
Deborah 1-night trip
Posted 1 day ago
Offshore Montauk

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. Wades Beach 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.