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Shelter Island Vacation Rentals

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Check prices for these dates

Tonight
7 Aug - 8 Aug
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8 Aug - 9 Aug
This weekend
8 Aug - 10 Aug
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15 Aug - 17 Aug

Vacation Rentals in Shelter Island

Montauk Manor
Stunning multi-story building with a traditional design, featuring balconies and a beautifully manicured lawn.

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1226)
"Nice historic place"
The price is RM1,255
RM1,517 total
includes taxes & fees
1 Sept - 2 Sept
Montauk Manor
The Surf Club
Relax on the beach with comfortable lounge chairs and umbrellas, surrounded by serene ocean views.

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (268)
"Quiet, relaxing place to stay, great access to the beach and town!"
The price is RM1,422
RM1,854 total
includes taxes & fees
3 Sept - 4 Sept
The Surf Club
Montauk Oceanside Suites
Cozy living space with a dining table, sofa, and kitchenette, complete with a stove and refrigerator.

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (400)
"great place to stay"
The price is RM935
RM1,114 total
includes taxes & fees
4 Sept - 5 Sept
Montauk Oceanside Suites
Windward Shores Ocean Resort
Enjoy a panoramic ocean view from the comfort of this room, featuring a dining table, seating area, and sliding glass doors to the outdoor patio.

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 RM913
RM1,135 total
includes taxes & fees
3 Sept - 4 Sept
Windward Shores Ocean Resort
Cliffside Resort Condominiums
Stunning beachfront residential area with multi-story buildings and a central park.

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (233)
"Great location, great views. Walls are a little thin."
The price is RM1,565
RM1,971 total
includes taxes & fees
1 Sept - 2 Sept
Cliffside Resort Condominiums
Driftwood Resort
Enjoy cooking in this well-equipped kitchen with a tiled backsplash and black refrigerator.

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 RM1,047
RM1,334 total
includes taxes & fees
3 Sept - 4 Sept
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
"The renovations were a total success!"
denise 1-night trip
Posted 15 hours ago
Offshore Montauk

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 84 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. Wades Beach and Gardiner's Bay Country Club 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.