Southold Vacations from ￥264,764

Book a Hotel + Flight or Car together to unlock savings

Photo by Benny Goh

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ￥45,448 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

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

The Latest Southold Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
Oct 23 - Oct 28
found 21 hours ago
Roundtrip flight included
Tokyo (HND) to New York (JFK)
9/10 Wonderful! (2,714 reviews)
Our stay was amazing. Highly recommend. We'll be staying again.

Reviewed on Jul 31, 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
per person
Sep 19 - Sep 24
found 21 hours ago
Roundtrip flight included
Tokyo (TYO) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
Exceedingly above my expectations

Reviewed on Jul 31, 2025

Pendry Manhattan West

Pendry Manhattan West

5 out of 5
Manhattan
Save 100% on your flight
per person
Sep 19 - Sep 24
found 21 hours ago
Roundtrip flight included
Tokyo (TYO) to New York (JFK)
9.8/10 Exceptional! (427 reviews)
The architecture and interior design was first rate. One of the best rooms I’ve ever stayed in

Reviewed on Jul 28, 2025

Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
Save 100% on your flight
per person
Sep 19 - Sep 25
found 1 day ago
Roundtrip flight included
Tokyo (HND) to New York (JFK)
7.8/10 Good! (2,087 reviews)
friendly staff. very nice room quick check in

Reviewed on Aug 2, 2025

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Save 100% on your flight
per person
Sep 19 - Sep 24
found 21 hours ago
Roundtrip flight included
Tokyo (TYO) to New York (JFK)
9.6/10 Exceptional! (116 reviews)
The hotel was phenomenal! We were greeting so warmly on arrival and given great dining and neighborhood tips by Ben- who was wonderful. The rooms were beautiful and all aspects of the hotel and dining/ bar spaces were gorgeous and full of character. We enjoyed The Portrait Bar a couple of times and had such fun. We also had breakfast in the restaurant and a spectacular dinner at Cafe Carmellini. I wish I could remember our server’s name because she was top notch. I will go back to The Fifth Avenue Hotel. It was a wonderful experience.

Reviewed on Jul 28, 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 ￥54,644 per night from Aug 7 to Aug 8
￥54,644
￥66,200 total
Aug 7 - Aug 8
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

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 ￥12,210 per night from Sep 2 to Sep 3
￥12,210
￥13,950 total
Sep 2 - Sep 3
includes taxes & fees
7/10 Good! (659 reviews)
"Nice and clean."

Reviewed on Jul 28, 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.

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

￥21,858
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

￥20,529
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?
You can snap up a vacation package to this top destination from ￥264,764 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.