Southold Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Southold Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Chelsea Pines Inn

Chelsea Pines Inn

2.5 out of 5
Manhattan
per person
4 Jun - 8 Jun
found 1 day ago
Return direct flight included
Madison (MSN) to New York (JFK)
8.2/10 Very good! (958 reviews)
nice place, room is elementary, small, very noisy

Reviewed on 25 Mar,2025

Park Lane New York

Park Lane New York

5 out of 5
Manhattan
Save 100% on your flight
per person
4 Jun - 8 Jun
found 1 day ago
Return direct flight included
Madison (MSN) to New York (JFK)
8.6/10 Excellent! (1,401 reviews)
Would like coffee maker in room.

Reviewed on 25 Mar,2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
per person
4 Jun - 8 Jun
found 1 day ago
Return direct flight included
Madison (MSN) to New York (JFK)
9.8/10 Exceptional! (1,133 reviews)
We loved the location between Chinatown and little Italy. It was only a few blocks to SoHo shopping and the subway station. The staff was very nice and the room was small but perfect for me and my daughter. The lobby had a coffee and ice machine and there was a little fridge with soda and sparkling water for a couple bucks. Nothing Wow but it was a great stay. I will definitely book there again when we return to NYC

Reviewed on 24 Mar,2025

PUBLIC, an Ian Schrager hotel

PUBLIC, an Ian Schrager hotel

4 out of 5
Manhattan
Save 100% on your flight
per person
4 Jun - 8 Jun
found 1 day ago
Return direct flight included
Madison (MSN) to New York (JFK)
8.2/10 Very good! (2,806 reviews)
Always happy to return

Reviewed on 25 Mar,2025

Dream Downtown, by Hyatt

Dream Downtown, by Hyatt

4.5 out of 5
Manhattan
Save 100% on your flight
per person
4 Jun - 8 Jun
found 1 day ago
Return direct flight included
Madison (MSN) to New York (JFK)
7.8/10 Good! (1,358 reviews)
Great location to walk to restaurants, shopping & outdoor activities. Definitely would recommend it to anyone.

Reviewed on 26 Mar,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 S$292 per night from 9 Apr to 10 Apr
S$292
includes taxes & fees
9 Apr - 10 Apr
9.4/10 Exceptional! (154 reviews)
"great location and view"

Reviewed on 19 Mar,2025

The Shoals Suites and Slips
Water's Edge Resort & Spa
Water's Edge Resort & Spa
3.5 out of 5
1525 Boston Post Road, Westbrook, CT
Fully refundableReserve now, pay when you stay
The price is S$313 per night from 31 Mar to 1 Apr
S$313
includes taxes & fees
31 Mar - 1 Apr
8.6/10 Excellent! (1,000 reviews)
"Everything was excellent, especially the beach and walking areas. The only downside was that the walls were thin so if the adjacent rooms are full you can hear everything going on next door. Other than that, very happy with everything."

Reviewed on 24 Mar,2025

Water's Edge Resort & Spa
Hyatt Place Long Island East End
Hyatt Place Long Island East End
3 out of 5
451 East Main Street, Riverhead, NY
Fully refundableReserve now, pay when you stay
The price is S$194 per night from 1 Apr to 2 Apr
S$194
includes taxes & fees
1 Apr - 2 Apr
9/10 Wonderful! (1,000 reviews)
"Fabulous stay! Clean room, great staff! In the middle of a sweet town! Next door to the aquarium ."

Reviewed on 17 Mar,2025

Hyatt Place Long Island East End
See all 4,267 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 holiday package cost?
You can snap up a holiday package to this top destination from S$1,243 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.

Popular places to visit

Croteaux Vineyards

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

Croteaux Vineyards

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

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.