Compare Shelter Island Resorts

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Featured Resorts in Shelter Island

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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.

Hotel Options in Shelter Island

    Gurney's Montauk Resort & Seawater Spa

    Gurney's Montauk Resort & Seawater Spa

    290 Old Montauk Highway Montauk NY
    $418 nightly
    The price is $478 total per night from Jan 25 to Jan 26
    $478 total
    Jan 25 - Jan 26
    Total with taxes and fees
    8.2/10 Very Good! (707 reviews)
    Water's Edge Resort & Spa

    Water's Edge Resort & Spa

    1525 Boston Post Road Westbrook CT
    $244 nightly
    The price is $281 total per night from Jan 4 to Jan 5
    $281 total
    Jan 4 - Jan 5
    Total with taxes and fees
    8.8/10 Excellent! (1,001 reviews)
    Montauk Blue Hotel

    Montauk Blue Hotel

    108 South Emerson Avenue Montauk NY
    9.2/10 Wonderful! (187 reviews)

Resort Hotels

Resort hotels in Shelter Island
Find your next great getaway when you book at a resort hotel in Shelter Island. Resorts are great for families or couples, or even solo travelers looking for a piece of paradise. Sure, you can leave your hotel and explore Shelter Island at your leisure…but with everything these sorts of hotels offer, you may never want to. From food and shopping to entertainment and organized tours, a resort hotel in Shelter Island is a great way to score an amazing vacation—and Orbitz can help you get there.

Resort hotels for everyone in Shelter Island
If you’re traveling with the kids, you know how hard it is to keep them entertained. Let them have some fun on their own: some resorts have clubs for the kiddos, including kid-friendly pools and adventure camps where they can explore, do some crafts and even take part in learning activities. (Don’t worry, no one will tell them this vacation is actually educational.) Of course, there’s plenty for adults to do at Shelter Island resorts as well. Take a yoga class, book a few treatments at the spa, or do a little shopping. Go ahead, charge it to the room. You’re on vacation!

Ready to wow your special someone? Plan a romantic getaway complete with luxury accommodations. Surprise your partner with a couples massage, followed by a candlelit dinner at the 5-star on-site hotel. Some of these luxury hotels even have adults-only pools with swim-up bars so you can float about with a couple of cocktails, watching the sunset and enjoying your time together.

Shelter Island Resorts essential information

Accommodation
14 Resorts
Lowest Price
$281
Highest Price
$478
Popular accommodation
Gurney's Montauk Resort & Seawater Spa, Water's Edge Resort & Spa, Brand New Waterfront - Chic & Sophisticated Unit # 702, Brand New Waterfront - Chic & Sophisticated, Duryea's Sunset Cottages, Brand New Waterfront - Chic & Sophisticated Unit # 703, Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6, Water's Edge Resort & Spa May 23, 2025 - May 30, 2025, Brand New Waterfront - Chic & Sophisticated Unit # 704

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