Southold Vacations from ₩1,745,646

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The Latest Southold Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Now Now NoHo

Now Now NoHo

2 out of 5
Manhattan
per person
Sep 21 - Sep 26
found 14 hours ago
Roundtrip non-stop flight included
Seoul (ICN) to New York (JFK)
8.2/10 Very Good! (232 reviews)
The room was tiny. 5’ X 8’ but really inexpensive and very clean and comfortable

Reviewed on Aug 13, 2025

Hotel 27 by LuxUrban

Hotel 27 by LuxUrban

2.5 out of 5
Manhattan
Save 100% on your flight
per person
Sep 21 - Sep 26
found 14 hours ago
Roundtrip non-stop flight included
Seoul (ICN) to New York (JFK)
7.6/10 Good! (852 reviews)
Their phone hasn't worked so I couldn't call down to the desk. Also they claimed that they never received payment from Expedia so everyone who registered that way had to give them a credit card again even if we paid in full already. I got the payment taken off, but not sure if they were trying to scam us

Reviewed on Aug 11, 2025

Millennium Hotel Broadway Times Square

Millennium Hotel Broadway Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
Sep 21 - Sep 26
found 14 hours ago
Roundtrip non-stop flight included
Seoul (ICN) to New York (JFK)
7.6/10 Good! (5,496 reviews)
It was clean and well located

Reviewed on Aug 14, 2025

Candlewood Suites New York City-Times Square by IHG

Candlewood Suites New York City-Times Square by IHG

2.5 out of 5
Manhattan
per person
Sep 21 - Sep 26
found 14 hours ago
Roundtrip non-stop flight included
Seoul (ICN) to New York (JFK)
8.4/10 Very Good! (1,404 reviews)
Friendly staff. Room was big enough for the two of us

Reviewed on Aug 12, 2025

Romer Hell's Kitchen

Romer Hell's Kitchen

4 out of 5
Manhattan
per person
Sep 21 - Sep 26
found 14 hours ago
Roundtrip non-stop flight included
Seoul (ICN) to New York (JFK)
9.4/10 Exceptional! (1,924 reviews)
Great hotel, sweet staff, very clean!

Reviewed on Aug 12, 2025

Find the Best Southold Vacation Packages

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 ₩512,717 per night from Aug 27 to Aug 28
₩512,717
₩620,257 total
Aug 27 - Aug 28
includes taxes & fees
9.4/10 Exceptional! (191 reviews)
"The hotel was lovely"

Reviewed on Aug 9, 2025

The Shoals Suites and Slips
Vine & Sand

Vine & Sand

3 out of 5
47100 New York 25, Southold, NY
10/10 Exceptional! (9 reviews)
"Beautiful house and trip to stay in the North Fork. Hosts are incredible. Highly recommend!!"

Reviewed on Jul 23, 2025

Get rates
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 ₩129,576 per night from Aug 17 to Aug 18
₩129,576
₩148,040 total
Aug 17 - Aug 18
includes taxes & fees
7.2/10 Good! (682 reviews)
"Nicely renovated."

Reviewed on Aug 10, 2025

Greenview Inn Riverhead
See all 4,326 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.

Frequently asked questions

How much does a Southold vacation package cost?
You can snap up a vacation package to this top destination from ₩1,745,646 on Expedia. However, how much your vacation to Southold costs will depend on the length of stay, hotel choice and season.
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 quieter months means you can generally find better prices on flights and hotels.
How many days is enough for Southold?
Dedicate at least 3 days for your Southold vacation to immerse yourself in everything that makes this place unique. Explore popular areas, including Greenport West and Pipes Cove. Then head to the major sights like Osprey's Dominion and Croteaux Vineyards. With a good itinerary, you can keep busy with room for some me-time too. Want to travel beyond Southold? Consider an excursion or two.
How to find the best Southold package deals?
Bagging a cheap Southold package deal is a cinch with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can tweak your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Southold package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Southold vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and hotels individually. Better still, you can personalize your Southold escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Southold?
If you're planning a spur-of-the-moment Southold vacation, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Southold?

  1. Choose your dates: The things you'd like to do in Southold and your favorite season can help you decide when to travel.
  2. Work out your budget: Ensure you have enough money to pay for everything from transportation and meals to flights and experiences. Your accommodations will likely be the largest expense during your trip to Southold.
  3. Decide how long to go for: Now that you know more about Southold, you can work out the perfect length of your break. Put together a rough itinerary and allocate enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a customized Southold vacation package.

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