Compare Southold Cottage Rentals

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Featured Southold 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 Southold

    The Shoals Suites and Slips

    The Shoals Suites and Slips

    61600 Main Rd, Southold, NY
    The price is $240 per night from May 4 to May 5
    $240
    includes taxes & fees
    $213 per night
    May 4 - May 5
    9.4/10 Exceptional! (157 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! (1,001 reviews)

Cottages

Book a cottage in Southold
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Southold. 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 Southold better.

Cottage apartments in Southold 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 Southold
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 Southold 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 Southold 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 Southold. 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.

Southold Cottages essential information

Accommodation
215 Cottages
Lowest Price
$102
Highest Price
$246
Popular accommodation
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