Southold Vacation Packages

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    Save up to CA $775 when you book a flight and hotel together*
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Top Southold Vacation Deals

The Westin New York Grand Central
The Towers at Lotte New York Palace
Lotte New York Palace
Hotel Riu Plaza New York Times Square
1 Hotel Brooklyn Bridge
Prices and availability subject to change. Additional terms may apply.

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 CA $270 per night from Mar. 31 to Apr. 1
CA $270
CA $342 total
includes taxes & fees
Mar 31 - Apr 1
9.4/10 Exceptional! (65 reviews)
"We try and come here every year we love it staff is so friendly and nice. I had to check out early while the office was closed and they accommodated me. Love this place"

Reviewed on Feb. 25, 2024

The Shoals Suites and Slips
Hilton Garden Inn Riverhead
Hilton Garden Inn Riverhead
3 out of 5
2038 Old Country Rd, Riverhead, NY
Fully refundableReserve now, pay when you stay
The price is CA $149 per night from Apr. 3 to Apr. 4
CA $149
CA $170 total
includes taxes & fees
Apr 3 - Apr 4
8.6/10 Excellent! (1,004 reviews)
"Convenient to wedding venue. Clean and in good condition"

Reviewed on Mar. 26, 2024

Hilton Garden Inn Riverhead
Residence Inn by Marriott New York Long Island East End
Residence Inn by Marriott New York Long Island East End
3 out of 5
2012 Old Country Road, Riverhead, NY
Fully refundableReserve now, pay when you stay
The price is CA $170 per night from Apr. 1 to Apr. 2
CA $170
CA $194 total
includes taxes & fees
Apr 1 - Apr 2
9/10 Wonderful! (744 reviews)
"The staff and hotel was excellent. I wii out old highly recommend staying here."

Reviewed on Mar. 24, 2024

Residence Inn by Marriott New York Long Island East End
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.

Explore other types of vacation packages

Frequently asked questions

How much does a Southold vacation package cost?
From just CA $859. Yes, you read that correctly. Our Southold packages are a simple way to make your budget go further. Combine your preferred flights, hotels and rental car and explore this popular destination.
How do I get a cheap travel package to Southold?
Search for flights that suit your busy schedule, add a hotel room to your booking and see how much you save with a Southold vacation package. It’s as easy as that! From flights and hotels to tours and rental cars, Expedia makes traveling cheap and easy. And with more than 550 air carriers and 1,000,000 properties worldwide to pick from, you’ll never be short of choice.
How far in advance should I book my Southold vacation?
Smart travelers will likely want to reserve their seats as early as possible. You can usually start comparing international airfares on Expedia up to 12 months before your flight. If you’re late to book, don’t stress. Cheap prices occasionally occur just weeks prior to departure.
What does an Expedia Southold travel package include?
Hotels, flights and car rentals — we bring you the very best deals. All you have to do is figure out your ideal combination. After you’ve made your booking, you can add on the fun stuff like sightseeing activities. Our travel packages make it easy to put together an awesome Southold escape.
What should I know before booking a Southold travel package?
So many places to wander around, so many things to see and do. With a package, you’ll be able to afford more of them. Bundle your hotels, flights and rental cars and see how much you save.
Can I choose my airline with a Southold Expedia vacation package?
Yes — and it’s easy too. Expedia has access to more than 550 partner airlines throughout the world. Our packages give you the freedom to take your pick of available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Southold vacation package?
If your travel plans in Southold have changed, it’s good to know that it is possible to cancel your booking. If you booked in the last 24 hours, you may be able to get a refund. If your booking is older than that, your hotel, airline or car rental company may charge a fee. To learn more, check our Customer Service Portal.

Discover the most popular places to visit in Southold

What to do in Southold

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