Southold Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Benny Goh
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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Your Southold Vacation

The coastal scenery and rich history are just the beginning of the things Southold has going for it. Experience the very best of this interesting city your way with a customized Southold vacation package. 67 Steps Beach, Raphael Winery and Railroad Museum of Long Island are just some of the many sights worth checking out during your trip to Southold. A few quick clicks is all it takes to put together your ideal Southold vacation on Expedia.

Top Southold Vacation Deals

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham Secaucus Meadowlands
Sound View Greenport
1 Hotel Brooklyn Bridge
Hotel 27 by LuxUrban
Arthouse Hotel New York City

Ready to book your vacation to Southold?

 

Choose your dates

Southold Hotel Deals

The Shoals Suites and Slips
The Shoals Suites and Slips
3.5 out of 5
61600 Main Rd, Southold, NY
9.4/10 Exceptional! (178 reviews)
"Great property"

Reviewed on Jul. 10, 2025

The Shoals Suites and Slips
Quality Inn Old Saybrook - Westbrook
Quality Inn Old Saybrook - Westbrook
2.5 out of 5
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Aug 3 to Aug 4
CA $151
CA $174 total
Aug 3 - Aug 4
includes taxes & fees
7.6/10 Good! (1,005 reviews)
"Very satisfied"

Reviewed on Jul. 9, 2025

Quality Inn Old Saybrook - Westbrook
Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex
2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is CA $105 per night from Jul 15 to Jul 16
CA $105
CA $121 total
Jul 15 - Jul 16
includes taxes & fees
7.6/10 Good! (989 reviews)
"The roadside in exceeded my expectations in all areas"

Reviewed on Jul. 9, 2025

Pier Blue Inn Old Saybrook - Essex
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.

What to do in Southold

Frequently asked questions

How much does a Southold vacation package cost?
Offering great value package deals from CA $594 on Expedia, you'll be pleasantly surprised at how much a vacation to Southold costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Southold?
January, February and March are great times to look for cheap Southold vacation packages. Choosing to travel in less busy periods means you can generally find reduced prices on flights and hotels.
How many days is enough for Southold?
Dedicate around 3 days for your Southold vacation in order to enjoy all that makes this destination unique. Wander around key areas, including Greenport West and Pipes Cove. Then make a beeline for major sights such as Peconic Bay Winery and Sparkling Pointe. With a clever itinerary, you can keep busy with room for some me-time too. Want to venture beyond Southold? Consider a day trip or two.
How to find the best Southold package deals?
Begin your search for a Southold package deal by entering your destination and preferred trip dates under our "Packages" tab. Then select some filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Southold package deal straight away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Southold getaway off to a flying start.
Is it cheaper to book a Southold vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll generally land a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Southold vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Southold?
If you've got your Southold travel dates locked in, book early to bag some unbeatable deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Southold?

  1. Choose the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Southold.
  2. Set a budget: Consider expenses such as flights, food and transportation when calculating how much to save for your trip to Southold. Then, pick a property that works with your budget, whether that's an affordable stay or a more upscale getaway.
  3. Set the duration of your trip: Start by listing all the attractions and activities you'd like to get to in Southold. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your accommodations and airfare: Once you've settled on your trip dates and duration, book the perfect Southold vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.