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Shelter Island Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Shelter Island vacation rentals

Condo | Terrace/patio

1. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (293 reviews)
"Great place!"
United States
Christine
The price is AED 1,067
AED 1,627 total
includes taxes & fees
28 Sep - 29 Sep
Cliffside Resort Condominiums
Flat-screen TV

2. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (57 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is AED 1,040
AED 1,188 total
includes taxes & fees
18 Oct - 19 Oct
North Fork Resort
Iron/ironing board, WiFi (free), individually decorated

3. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (323 reviews)
"Easy access to the beach. Perfect weather. Nicely furnished and updated rooms and bathrooms. The gym is tiny- not much equipment. The location is perfect for Montauk and Amagansett. The staff were very nice and hard working."
United States
Gaurang J
The price is AED 437
AED 599 total
includes taxes & fees
12 Oct - 13 Oct
Windward Shores Ocean Resort
Apartment | WiFi (free), individually decorated, individually furnished, bed sheets

4. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
8.8 out of 10, Excellent, (251 reviews)
"Best value and bang for your buck in Montauk other than Wavecrest in Amagansett."
United States
William
The price is AED 601
AED 806 total
includes taxes & fees
4 Oct - 5 Oct
Driftwood Resort
Lobby

5. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,406 reviews)
"Excellent service, beautiful property, accommodating staff."
United States
Maria
The price is AED 474
AED 613 total
includes taxes & fees
12 Oct - 13 Oct
Montauk Manor
Apartment | Iron/ironing board, WiFi (free)

6. Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (452 reviews)
"The room was very clean and spacious."
United States
Jadana
The price is AED 434
AED 536 total
includes taxes & fees
20 Oct - 21 Oct
Montauk Oceanside Suites
Apartment | Living area

7. The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (297 reviews)
"Found mold under the pull-out couch"
United States
Anna
The price is AED 702
AED 1,030 total
includes taxes & fees
23 Sep - 24 Sep
The Surf Club
One Bedroom Residence King with Ocean View | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

8. Offshore Spa & Residences

Offshore Spa & Residences
4.5 star property
Downtown Montauk
8.4 out of 10, Very good, (5 reviews)
"⭐⭐⭐⭐⭐ We had such a wonderful stay at Offshore Montauk! The hotel is beautifully designed, incredibly clean, and the location couldn’t be better—just steps from the beach and an easy walk to Montauk’s restaurants and shops. The rooms are stylish, comfortable, and so peaceful. We especially loved the pool, sauna, and cold plunge—they were the perfect way to relax and recharge after a day at the beach. Most importantly, the staff was genuinely welcoming and made us feel at home from the moment we...
United States
Iryna
The price is AED 2,046
AED 2,757 total
includes taxes & fees
4 Oct - 5 Oct
Offshore Spa & 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

Ocean Vista Resort

Ocean Vista Resort

10/10 Excellent
"Awesome location by the beach and friendly staff. Great place to stay for a beach getaway!"
Dan 2-night trip
Posted 1 hour ago
Ocean Vista Resort

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.

What are some of the best vacation home rentals that Shelter Island has to offer?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : This vacation home rental near Shelter Island is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a patio and a garden.

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 Mashomack Preserve are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Shelter Island Whale's Tail. Shelter Island Historical Society and Crescent Beach 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.