Compare Southold Resorts

Start date: Check-in selected.
To Date
End date: Check-out

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Resorts in Southold

Don't see what you're looking for?
See all available properties in Southold
View all properties
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
    $160 nightly
    The price is $183 total per night from Jan 14 to Jan 15
    $183 total
    Jan 14 - Jan 15
    Total with taxes and fees
    9.4/10 Exceptional! (234 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 11 to Jan 12
    $281 total
    Jan 11 - Jan 12
    Total with taxes and fees
    8.8/10 Excellent! (1,006 reviews)
    Pier Blue Inn Old Saybrook - Essex

    Pier Blue Inn Old Saybrook - Essex

    1430 Boston Post Rd Old Saybrook CT
    $74 nightly
    The price is $85 total per night from Jan 11 to Jan 12
    $85 total
    Jan 11 - Jan 12
    Total with taxes and fees
    7.8/10 Good! (1,001 reviews)

Resort Hotels

Resort hotels in Southold
Find your next great getaway when you book at a resort hotel in Southold. 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 Southold 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 Southold is a great way to score an amazing vacation—and Orbitz can help you get there.

Resort hotels for everyone in Southold
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 Southold 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.

Southold Resorts essential information

Accommodation
8 Resorts
Lowest Price
$85
Highest Price
$281
Popular accommodation
Water's Edge Resort & Spa, 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, Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6, Ocean Colony Beach and Tennis Club, Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6, Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6, Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 4