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.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
per person
Oct 20 - Oct 23
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,004 reviews)
One of the nicest stays we've stayed And we stay at least in 20-25 hotels a year

Reviewed on Jul. 18, 2025

Outsite Chelsea

Outsite Chelsea

2 out of 5
Manhattan
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (8 reviews)
The place and amenities were really nice. The only bad thing was the bathroom got nasty really quick so for me the shared bathrooms won’t work. But they do have private bathroom rooms. Other than the dirty bathrooms not getting cleaned enough everything was great, location and space.

Reviewed on Jun. 25, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Oct 24 - Oct 26
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)
This place was amazing, from the bartender Josh to Seiki and Selina, and also JD the concierge, I know I’m leaving people out but the entire staff made our stay perfection, it was first class all the way and I would never stay anywhere else when we go back, just truly a first rate experience

Reviewed on Aug. 3, 2025

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (2,273 reviews)
Right across from the subway entrance, a Starbucks, and next to a Walgreens. Down the street, McD’s, Subway, Panda, CVS. Blocks away from Rockefeller Center. A block away from police and fire, felt safe the whole time. The property was modern and clean. We used the microwave in the lobby, our room had a fridge. Normal room size and not NY size, bed was comfortable and room was quiet! Definitely want to stay here again on the next trip.

Reviewed on Aug. 3, 2025

Omni Berkshire Place

Omni Berkshire Place

4 out of 5
Manhattan
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,897 reviews)
A reliable, comfortable, and convenient hotel in Manhattan. This is our third stay and we will be back.

Reviewed on Aug. 3, 2025

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Southold Hotel Deals

The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd, Southold, NY
The price is CA $513 per night from Aug 4 to Aug 5
CA $513
CA $620 total
Aug 4 - Aug 5
includes taxes & fees
9.4/10 Exceptional! (187 reviews)
Already Want to Return
"The property is beautiful- was nice to relax in the Adirondack chairs near the marina in the evenings. We stayed in the Grand Suite and everything was spotless and comfortable. As others have said, it is a bit easy to hear your neighbors through the walls at night, but nothing earplugs can’t fix ..."

Reviewed on Jul. 31, 2025

The Shoals Suites and Slips
Vine & Sand

Vine & Sand

3 out of 5
47100 New York 25, Southold, NY
10/10 Exceptional! (8 reviews)
"Beautiful house and trip to stay in the North Fork. Hosts are incredible. Highly recommend!!"

Reviewed on Jul. 23, 2025

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Vine & Sand
Greenview Inn Riverhead

Greenview Inn Riverhead

2 out of 5
1433 W Main St, Riverhead, NY
Fully refundableReserve now, pay when you stay
The price is CA $123 per night from Aug 4 to Aug 5
CA $123
CA $140 total
Aug 4 - Aug 5
includes taxes & fees
7/10 Good! (667 reviews)
"New clean room"

Reviewed on Aug. 2, 2025

Greenview Inn Riverhead
See all 4,338 properties in Southold
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.
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What to do in Southold

Join a small group full-day wine tour with a certified Sommelier host

Long Island Wine and Food Day Trip with Sommelier host from NYC

CA $203
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting

From Mattituck: North Fork Area Bike Tour with Food Tasting

CA $190
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
See all activities in Southold

Frequently asked questions

How much does a Southold vacation package cost?
Offering great value package deals from CA $768 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.