Southold Vacations from ₩1,626,754

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The Latest Southold Vacation Packages

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

Outsite Chelsea

2 out of 5
Manhattan
Save 100% on your flight
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Seoul (ICN) to New York (JFK)
9.8/10 Exceptional! (6 reviews)
The place and amenities were really nice. The only bad thing was the bathroom got nasty really quick so for me the shared bathrooms won’t work. But they do have private bathroom rooms. Other than the dirty bathrooms not getting cleaned enough everything was great, location and space.

Reviewed on Jun 25, 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Seoul (ICN) to New York (JFK)
9.8/10 Exceptional! (1,232 reviews)
I’ve returned from a 5 days mother/son trip to NYC with my 14 yrs old..The experience was fantastic and staying at NobleDen made it even more special…Property was clean and quiet and the area was very safe even for late night walks…we will definitely be back ..

Reviewed on Jul 14, 2025

The Lexington Hotel, Autograph Collection

The Lexington Hotel, Autograph Collection

4 out of 5
Manhattan
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Seoul (ICN) to New York (JFK)
8.2/10 Very Good! (1,275 reviews)
Would hinge on being a five star property except for restaurant and bar which are open a few a few hours a day and have the menu and quality consistent with such. Mandatory $35.00 daily fee per room will cover one drink when bar is open.

Reviewed on Jul 14, 2025

The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Manhattan
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Seoul (ICN) to New York (JFK)
8.8/10 Excellent! (1,653 reviews)
Another great stay at the Shelburne (3rd time). Excellent service, large room (for NYC), and convenient location.

Reviewed on Jul 14, 2025

Millennium Hilton New York One UN Plaza

Millennium Hilton New York One UN Plaza

4 out of 5
Manhattan
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Seoul (ICN) to New York (JFK)
8.2/10 Very Good! (1,864 reviews)
The hotel was in a quiet area but easily accessible by car, public transport or by walking. Staff are polite and accessible and always see them with a smile

Reviewed on Jul 13, 2025

Find the Best Southold Vacation Packages

Southold Hotel Deals

The Shoals Suites and Slips
The Shoals Suites and Slips
3.5 out of 5
61600 Main Rd, Southold, NY
9.4/10 Exceptional! (180 reviews)
"Great property"

Reviewed on Jul 10, 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
Fully refundableReserve now, pay when you stay
The price is ₩152,176 per night from Aug 3 to Aug 4
₩152,176
₩175,002 total
Aug 3 - Aug 4
includes taxes & fees
7.6/10 Good! (1,008 reviews)
Excellent Place to Stay!!!...5 Stars & More!!
"We stayed 5 days! Customer service was great ;) Housekeeping was great, the cafe in the morning was excellent! Lounge area if you wanted to go out in the evening they had Pool, Darts, & Karaoke If you didn't want to go to the Beach, they had a Pool/Gym Right near the Highway & Route 1 We had a wonderful ..."

Reviewed on Jul 10, 2025

Quality Inn Old Saybrook - Westbrook
Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex
2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is ₩110,310 per night from Jul 15 to Jul 16
₩110,310
₩126,856 total
Jul 15 - Jul 16
includes taxes & fees
7.6/10 Good! (989 reviews)
"The roadside in exceeded my expectations in all areas"

Reviewed on Jul 9, 2025

Pier Blue Inn Old Saybrook - Essex
See all 4,409 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 vacation package cost?
You can snap up a vacation package to this top destination from ₩1,626,754 on Expedia. However, how much your vacation 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 vacation 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 vacation 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 vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and hotels individually. Better still, you can personalize 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 vacation package to Southold?
If you're planning a spur-of-the-moment Southold vacation, 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 favorite 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 accommodations 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 customized Southold vacation package.

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