Southold Holidays

Photo by Benny Goh

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Top Flight + Hotel Deals in Southold

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

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was €1,513, price is now €919 per person
€919
per person
31 Oct - 3 Nov
found 11 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (3,368 reviews)
One block from Times Square busy yet so centrally located to all we wanted to see! We enjoyed the hotel and we could walk or use the subway system just on the corner. Many nearby restaurants and stores. Great service and clean rooms! Wifi is an additional charge.

Reviewed on 18 Aug 2025

Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
Save 100% on your flight
Price was €1,772, price is now €950 per person
€950
per person
7 Oct - 13 Oct
found 1 day ago
Return flight included
Toronto (YYZ) to New York (JFK)
8/10 Very Good! (2,135 reviews)
I really enjoyed the hotel. It was perfect for me and my partner. It was just the two of us. I did search a lot for a hotel with a balcony and I finally found this one. I will definitely recommend it. I will definitely come back again.

Reviewed on 19 Aug 2025

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Price was €2,297, price is now €1,295 per person
€1,295
per person
9 Oct - 14 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (1,582 reviews)
Mattress was very uncomfortable.

Reviewed on 18 Aug 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was €2,000, price is now €1,171 per person
€1,171
per person
9 Oct - 14 Oct
found 24 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.8/10 Exceptional! (1,271 reviews)
Great location. Nice set up. Write in Little Italy.

Reviewed on 19 Aug 2025

Pestana Park Avenue

Pestana Park Avenue

4 out of 5
Manhattan
Save 100% on your flight
Price was €2,095, price is now €1,242 per person
€1,242
per person
30 Oct - 5 Nov
found 1 hour ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (688 reviews)
The front desk staff were very friendly, the room was clean and spacious.

Reviewed on 15 Aug 2025

Top hotels in Southold

The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd, Southold, NY
The price is €385 per night from 26 Aug to 27 Aug
€385
26 Aug - 27 Aug
includes taxes & fees
9.4/10 Exceptional! (192 reviews)
"The hotel was lovely"

Reviewed on 9 Aug 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 23 Jul 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
7.2/10 Good! (699 reviews)
"Nice"

Reviewed on 18 Aug 2025

Get rates
Greenview Inn Riverhead
See all 4,307 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.

Popular places to visit

Corey Creek Winery

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.

Corey Creek Winery

Horton Point Park

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.

Horton Point Park

Mattebella Vineyards

You can enjoy a tasting or tour at Mattebella Vineyards during your travels to Southold. Wander the beautiful beaches in this family-friendly area.

Mattebella Vineyards

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

€128
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

€120
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 holiday package cost?
You can snap up a holiday package to this top destination from €919 on Expedia. However, how much your holiday 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 holiday 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 holiday 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 holiday as a package?
An Expedia holiday package could score you significant savings when compared to booking flights and hotels individually. Better still, you can personalise 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 holiday package to Southold?
If you're planning a spur-of-the-moment Southold holiday, 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 favourite 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 accommodation 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 customised Southold holiday package.

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