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.
Hudson Yards Hotel

Hudson Yards Hotel

2 out of 5
Manhattan
per person
24 Mar - 29 Mar
found 14 hours ago
Return direct flight included
Los Angeles (LAX) to New York (JFK)
6.6/10 (434 reviews)
The hotel was great for the 3 day stay. The outline of the hotel was pretty strange but it was nice otherwise. Close to time square.

Reviewed on 13 Jan,2025

Oracle of New York Suites

Oracle of New York Suites

2 out of 5
Manhattan
Save 100% on your flight
per person
24 Mar - 29 Mar
found 14 hours ago
Return direct flight included
Los Angeles (LAX) to New York (JFK)
10/10 Exceptional! (1 review)
Great host mixed with great house which results in reasonable price. All in all, great experience.

Reviewed on 16 Dec,2024

The Herald by LuxUrban

The Herald by LuxUrban

2.5 out of 5
Manhattan
Save 100% on your flight
per person
24 Mar - 29 Mar
found 14 hours ago
Return direct flight included
Los Angeles (LAX) to New York (JFK)
7.8/10 Good! (312 reviews)
Would recommend property to friends and would definitely book again. Jon who checked us in was very welcoming and accommodating. Thanks for a wonderful stay.

Reviewed on 11 Jan,2025

Tuscany by LuxUrban

Tuscany by LuxUrban

3 out of 5
Manhattan
per person
24 Mar - 29 Mar
found 14 hours ago
Return direct flight included
Los Angeles (LAX) to New York (JFK)
8.2/10 Very Good! (1,009 reviews)
The property is in walking distance to Grand Central Station, the room was clean and a very nice size. The front desk staff are amiable and willing to assist. Because it is a hotel in the centers in the city the hotel has limited onsite activities and if you are there to sleep in you may not get maid service as it appear’s as if they only come around once. I enjoyed my stay overall and would return and or recommend.

Reviewed on 13 Jan,2025

Hyatt Herald Square New York

Hyatt Herald Square New York

4 out of 5
Manhattan
per person
24 Mar - 29 Mar
found 14 hours ago
Return direct flight included
Los Angeles (LAX) to New York (JFK)
8.6/10 Excellent! (1,005 reviews)
Relatively good location. Close enough yet far enough from time square. Average rooms. Not the greatest surrounding area but overall okay. Again average.

Reviewed on 14 Jan,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$264 per night from 10 Feb to 11 Feb
S$264
includes taxes & fees
10 Feb - 11 Feb
9.4/10 Exceptional! (145 reviews)
"I can’t say enough great things about this place. Absolutely wonderful !"

Reviewed on 4 Jan,2025

The Shoals Suites and Slips
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$184 per night from 27 Jan to 28 Jan
S$184
includes taxes & fees
27 Jan - 28 Jan
9/10 Wonderful! (1,002 reviews)
"Just Great!"

Reviewed on 8 Jan,2025

Hyatt Place Long Island East End
Quality Inn Old Saybrook - Westbrook
Quality Inn Old Saybrook - Westbrook
2.5 out of 5
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is S$134 per night from 2 Feb to 3 Feb
S$134
includes taxes & fees
2 Feb - 3 Feb
7.4/10 Good! (1,002 reviews)
"Friendly and helpful staff and the breakfast was good. The only issue was one of the beds in our room (212) literally fell off the frame on one side when sat on.We were tired and had already settled in, so we didn’t request a new room and made it work."

Reviewed on 8 Jan,2025

Quality Inn Old Saybrook - Westbrook
See all 4,238 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$1,154 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.