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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 ₩413,281
₩499,416 total
includes taxes & fees
Sep 1 - Sep 2
Montauk Manor
Montauk Oceanside Suites
Apartment | Private kitchen | Fridge, microwave, stovetop

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (404)
"great place to stay"
The price is ₩276,147
₩330,625 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 ₩468,066
₩610,446 total
includes taxes & fees
Sep 3 - Sep 4
The Surf Club
Windward Shores Ocean Resort
Ocean View 2BD Corner King and Queen | Living area | TV

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 ₩268,118
₩336,608 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 ₩470,821
₩598,368 total
includes taxes & fees
Sep 11 - Sep 12
Cliffside Resort Condominiums
Driftwood Resort
Apartment, 1 Bedroom | Private kitchen | Fridge, microwave, cookware/dishes/utensils

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 ₩344,763
₩439,234 total
includes taxes & fees
Sep 3 - Sep 4
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

Baron's Cove

Baron's Cove

10/10 Excellent
"Barons Cove Inn is very well located i.e. walkable to pretty much everything. It’s also charming, somewhat quirky, clean, comfortable, has very nice room amenities and internet access, a friendly attentive staff, a nice bar and restaurant, a lovely pool, is waterfront and has a great front porch with rockers. What’s not to like? We’ll definitely be making return visits. "
Christine 3-night trip
Posted 2 days ago
Baron's Cove

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.