Southold Vacations from AED4,496

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The Latest Southold Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was AED6,439, price is now AED4,496 per person
AED4,496
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Dubai (DXB) to New York (JFK)
8.8/10 Excellent! (8,157 reviews)

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was AED7,045, price is now AED5,064 per person
AED5,064
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Dubai (DXB) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)
The bar cafe in the lobby was amazing! Quick check in, clean property and very spacious rooms for this price point in NYC

Reviewed on 13 November 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was AED7,042, price is now AED5,062 per person
AED5,062
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Dubai (DXB) to New York (JFK)
9/10 Wonderful! (3,435 reviews)

Sofitel New York

Sofitel New York

4.5 out of 5
Manhattan
Price was AED7,588, price is now AED5,868 per person
AED5,868
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Dubai (DXB) to New York (JFK)
9/10 Wonderful! (1,203 reviews)

PUBLIC, an Ian Schrager hotel

PUBLIC, an Ian Schrager hotel

4 out of 5
Manhattan
Price was AED7,879, price is now AED6,128 per person
AED6,128
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Dubai (DXB) to New York (JFK)
8.8/10 Excellent! (4,078 reviews)

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
The price is AEDĀ 681 per night from Nov 15 to Nov 16
AEDĀ 681
AEDĀ 870 total
15 Nov - 16 Nov
includes taxes & fees
9.4/10 Exceptional! (351 reviews)
"The shoals was a perfect place for our north fork adventures. The staff was very friendly and extremely accommodating! The location was beautiful and very relaxing."

Reviewed on 12 November 2026

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
Fully refundableReserve now, pay when you stay
The price is AEDĀ 285 per night from Nov 15 to Nov 16
AEDĀ 285
AEDĀ 328 total
15 Nov - 16 Nov
includes taxes & fees
Pier Blue Inn Old Saybrook - Essex
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 AEDĀ 489 per night from Nov 23 to Nov 24
AEDĀ 489
AEDĀ 626 total
23 Nov - 24 Nov
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"It was a lovely property and close to stores and places to eat."

Reviewed on 13 November 2026

Water's Edge Resort & Spa
See all 4,213 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.

Stay near popular Southold attractions

Sparkling Pointe

8.8/10 (11 reviews)
Sparkling Pointe crafts exquisite sparkling wines using traditional MĆ©thode Champenoise in their Southold vineyard. Savor their diverse bubblies in an elegant tasting room with vineyard views.
See properties

Frequently asked questions

How much does a Southold vacation package cost?
Offering great value package deals from AED4,496 on Expedia, you'll be pleasantly surprised at how much a vacation to Southold costs! Our packages mean less travel planning for you and greater savings.
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 less busy periods means you can generally find reduced prices on flights and hotels.
How to find the best Southold package deals?
Begin your search for a Southold package deal by entering your destination and preferred trip dates under our "Packages" tab. Then select some filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Southold package deal straight away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Southold getaway off to a flying start.
Is it cheaper to book a Southold vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll generally land a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Southold vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Southold?
If you've got your Southold travel dates locked in, book early to bag some unbeatable deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Southold?

  1. Choose the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Southold.
  2. Set a budget: Consider expenses such as flights, food and transportation when calculating how much to save for your trip to Southold. Then, pick a property that works with your budget, whether that's an affordable stay or a more upscale getaway.
  3. Set the duration of your trip: Start by listing all the attractions and activities you'd like to get to in Southold. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your accommodations and airfare: Once you've settled on your trip dates and duration, book the perfect Southold vacation package for you.