Compare Shelter Island Cottage Rentals

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Featured Shelter Island Cottages

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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

    Montauk Yacht Club

    Montauk Yacht Club

    32 Star Island Rd, Montauk, NY
    The price is $296 per night from May 4 to May 5
    $296
    includes taxes & fees
    $259 per night
    May 4 - May 5
    8.4/10 Very Good! (999 reviews)
    Pier Blue Inn Old Saybrook - Essex

    Pier Blue Inn Old Saybrook - Essex

    1430 Boston Post Rd, Old Saybrook, CT
    The price is $102 per night from May 4 to May 5
    $102
    includes taxes & fees
    $89 per night
    May 4 - May 5
    7.6/10 Good! (952 reviews)
    Water's Edge Resort & Spa

    Water's Edge Resort & Spa

    1525 Boston Post Road, Westbrook, CT
    The price is $246 per night from May 4 to May 5
    $246
    includes taxes & fees
    $214 per night
    May 4 - May 5
    8.6/10 Excellent! (1,002 reviews)

Cottages

Book a cottage in Shelter Island
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Shelter Island. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Shelter Island better.

Cottage apartments in Shelter Island range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Shelter Island
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Shelter Island and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Shelter Island cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Shelter Island. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Shelter Island Cottages essential information

Accommodation
225 Cottages
Lowest Price
$102
Highest Price
$296
Popular accommodation
Charming 3-bedroom cottage in Old Saybrook with WiFi and AC, Charming 3-bedroom cottage short walk to Chalker Beach, 1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets, The gardners Cottage 1 mile from long Island Sound - pet friendly, Enchanted Waterfront Cottage, Orient Village — Historic Bayfront Cottage — 2025 Season, Hampton Cottage., 'The Gate House'on Beach front Estate with Dockage. Walk to Village ., Location and views! Located directly on Shinnecock Bay!