Southold Vacation Packages
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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.
OYO Times Square
Manhattan
CA $1,506
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
6.8/10 (2,082 reviews)
I was really disappointed with our stay here. The staff was hardly helpful. A couple were pleasant to talk to but made hardly any effort to help us. Most of the seating downstairs had large stains on them. The room was super basic and either someone left some travel size products in the shower that weren’t cleaned out or they just had random brands left in the shower. It all just felt unprofessional. We will not be staying here again.
Reviewed on Sep 25, 2026
Ready to book your vacation to Southold?
Southold Hotel Deals
The Shoals Suites and Slips
61600 Main Rd Southold NY
CA $285
CA $361 total
Oct 1 - Oct 2
includes taxes & fees
9.4/10 Exceptional! (342 reviews)
"This place is awesome! It is very well appointed and very comfortable beds. It's a beautiful space with lots of outdoor space and lovely views of the small marina next door. We were in town for just one night, wish we could have stayed longer. I'd go back in a heartbeat!"
Reviewed on Sep 22, 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
CA $115
CA $133 total
Sep 29 - Sep 30
includes taxes & fees
8/10 Very good! (1,011 reviews)
"If wasn’t great at all. Staff was fine but room was just depressing."
Reviewed on Sep 25, 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
CA $253
CA $316 total
Oct 4 - Oct 5
includes taxes & fees
8.8/10 Excellent! (1,009 reviews)
"The staff at the Bistro Bar weren't very good. Also the drinks sub par. I ordered a gin and tonic, they served me soda water twice."
Reviewed on Sep 23, 2026
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.
Stay near popular Southold attractions
Sparkling Pointe
8.8/10 (11 reviews)
You can enjoy a tasting or tour at Sparkling Pointe during your travels to Southold. Discover the sunsets and wineries in this family-friendly area.
Croteaux Vineyards
10.0/10 (12 reviews)
You can enjoy a tasting or tour at Croteaux Vineyards during your travels to Southold. Wander the beautiful beaches in this family-friendly area.
Sannino's Bella Vita Vineyard
9.6/10 (4 reviews)
You can enjoy a tasting or tour at Sannino's Bella Vita Vineyard during your travels to Southold. Wander the beaches or discover the sunsets in this family-friendly area.
Horton Point Park
9.4/10 (3 reviews)
Explore the great outdoors at Horton Point Park, a lovely green space in Southold. Wander the beaches or discover the sunsets in this family-friendly area.
Osprey's Dominion
9.6/10 (5 reviews)
You can enjoy a tasting or tour at Osprey's Dominion during your travels to Southold. Wander the beautiful beaches in this family-friendly area.
Horton Lane Beach
9.0/10 (4 reviews)
Why not spend a lazy afternoon at Horton Lane Beach during your trip to Southold? Stroll along the beaches or discover the area's sunsets.
Mattebella Vineyards
8.0/10 (4 reviews)
You can enjoy a tasting or tour at Mattebella Vineyards during your travels to Southold. Wander the beautiful beaches in this family-friendly area.
Corey Creek Winery
9.6/10 (5 reviews)
You can enjoy a tasting or tour at Corey Creek Winery during your travels to Southold. Wander the beautiful beaches in this family-friendly area.
What to do in Southold
Full Day Private Long Island Wine Tours from New York City
CA $264
per adult
Frequently asked questions
How much does a Southold vacation package cost?
Offering great value package deals from CA $1,126 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?
- 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.
- 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.
- 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.
- 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.
