Southold Holidays

Photo by Benny Goh

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Southold Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Manhattan
per person
22 Jul - 25 Jul
found 1 day ago
Return flight included
San Francisco (SFO) to New York (JFK)
8.8/10 Excellent! (1,614 reviews)
Although we were to be offered an upgrade if available which did not happen and the room adjacent to ours was where families with babies were put with the attendant noise issues.

Reviewed on 17 Jun, 2025

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
per person
22 Jul - 25 Jul
found 1 day ago
Return flight included
San Francisco (SFO) to New York (JFK)
9/10 Wonderful! (2,729 reviews)
Great clean neat facility!!!!

Reviewed on 16 Jun, 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
per person
22 Jul - 25 Jul
found 1 day ago
Return flight included
San Francisco (SFO) to New York (JFK)
9.8/10 Exceptional! (1,199 reviews)
We enjoyed the location and the staff at this property. This is the second time we stayed there.

Reviewed on 16 Jun, 2025

Club Quarters Hotel, Grand Central

Club Quarters Hotel, Grand Central

4 out of 5
Manhattan
per person
22 Jul - 25 Jul
found 1 day ago
Return flight included
San Francisco (SFO) to New York (JFK)
9/10 Wonderful! (2,491 reviews)
Everything was wonderful. From the check-in to check-out and everything in between was great. I’ll be back in a couple of months!

Reviewed on 16 Jun, 2025

Hotel Seville Nomad, in the Unbound Collection by Hyatt

Hotel Seville Nomad, in the Unbound Collection by Hyatt

4.5 out of 5
Manhattan
per person
22 Jul - 25 Jul
found 1 day ago
Return flight included
San Francisco (SFO) to New York (JFK)
8.6/10 Excellent! (1,051 reviews)
Great Location, friendly staff, room was clean!

Reviewed on 17 Jun, 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$457 per night from 22 Jun to 23 Jun
S$457
22 Jun - 23 Jun
includes taxes & fees
9.4/10 Exceptional! (171 reviews)
"Amazing"

Reviewed on 15 Jun, 2025

The Shoals Suites and Slips
Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex
2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
The price is S$128 per night from 2 Jul to 3 Jul
S$128
2 Jul - 3 Jul
includes taxes & fees
7.6/10 Good! (974 reviews)
Not bad
"The location was great- cute town. The room was clean and pretty basic. Beds could have been more comfy. Overall, it was fine given the amount paid."

Reviewed on 13 Jun, 2025

Pier Blue Inn Old Saybrook - Essex
Baron's Cove
Baron's Cove
4 out of 5
31 West Water Street, Sag Harbor, NY
9/10 Wonderful! (251 reviews)
"Great location in the heart of town Walk to everything Amazing breakfast too"

Reviewed on 11 Jun, 2025

Get rates
Baron's Cove
See all 4,335 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$813 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

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

S$204
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
See all activities in Southold

* 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.