Travel to Southold

Photo by Benny Goh

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Southold Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Shoreham Hotel

The Shoreham Hotel

4 out of 5
Manhattan
per person
15 Sept - 18 Sept
found 22 hours ago
Return direct flight included
Kuala Lumpur (KUL) to New York (JFK)
7.6/10 Good! (1,219 reviews)
Great location, staff, and room cleanliness

Reviewed on 14 Jul 2025

The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Manhattan
per person
15 Sept - 18 Sept
found 22 hours ago
Return direct flight included
Kuala Lumpur (KUL) to New York (JFK)
8.8/10 Excellent! (1,653 reviews)
I stayed here because my daughter was in Langone Hospital and it was very convenient to walk there, and to restaurants. The room was quiet and comfortable.

Reviewed on 19 Jul 2025

Millennium Premier New York Times Square

Millennium Premier New York Times Square

4 out of 5
Manhattan
per person
15 Sept - 18 Sept
found 22 hours ago
Return direct flight included
Kuala Lumpur (KUL) to New York (JFK)
7.8/10 Good! (1,005 reviews)
Nice place And I encourage people go over there

Reviewed on 17 Jul 2025

Hampton Inn Manhattan/Times Square South

Hampton Inn Manhattan/Times Square South

2.5 out of 5
Manhattan
per person
15 Sept - 18 Sept
found 22 hours ago
Return direct flight included
Kuala Lumpur (KUL) to New York (JFK)
7.4/10 Good! (1,688 reviews)
Room are too tight, no room for luggage’s

Reviewed on 19 Jul 2025

Warwick New York

Warwick New York

4 out of 5
Manhattan
per person
15 Sept - 18 Sept
found 22 hours ago
Return direct flight included
Kuala Lumpur (KUL) to New York (JFK)
9/10 Wonderful! (1,600 reviews)
Our mother-daughter 5 night stay could not have been any better! Thank you to every member of the staff.

Reviewed on 20 Jul 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
9.4/10 Exceptional! (181 reviews)
Great Stay. Loved it.
"Such a great stay. We were so disappointed we were only staying for one night. We will be definitely staying here again."

Reviewed on 16 Jul 2025

Get rates
The Shoals Suites and Slips
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd, Old Saybrook, CT
The price is RM469 per night from 3 Aug to 4 Aug
RM469
RM539 total
3 Aug - 4 Aug
includes taxes & fees
7.6/10 Good! (1,004 reviews)
Swimming pool is the best
"The pool was the best part of the hotel. Warm and deep enough, long enough to actually swim some 1/2 laps"

Reviewed on 14 Jul 2025

Quality Inn Old Saybrook - Westbrook
Greenview Inn Riverhead

Greenview Inn Riverhead

2 out of 5
1433 W Main St, Riverhead, NY
7/10 Good! (644 reviews)
"Super clean and renovated rooms. Staff was very nice and professional."

Reviewed on 20 Jul 2025

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Greenview Inn Riverhead
See all 4,417 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

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

RM676
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

RM583
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 RM5,802 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.