Southold Holidays

Book a Hotel + Flight or Car together to unlock savings

Choose two or more items and save on your trip:
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to NZ$545 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Our pick of the best Southold Hotel Deals

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 NZ$210 per night from 2 May to 3 May
NZ$210
per night
2 May - 3 May
8.4/10 Very Good! (1,001 reviews)
"The room was clean and the location of the hotel was convenient."

Reviewed on 24 Apr. 2024

Hilton Garden Inn Riverhead
The Shoals Suites and Slips
The Shoals Suites and Slips
3.5 out of 5
61600 Main Rd, Southold, NY
The price is NZ$496 per night from 28 Apr to 29 Apr
NZ$496
per night
28 Apr - 29 Apr
9.4/10 Exceptional! (71 reviews)
"Wonderful stay, clean, spacious room. Lobby area is lovely."

Reviewed on 18 Apr. 2024

The Shoals Suites and Slips
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 NZ$258 per night from 1 May to 2 May
NZ$258
per night
1 May - 2 May
9/10 Wonderful! (758 reviews)
"Staff is Great!! lovely area and one of the best hotels."

Reviewed on 24 Apr. 2024

Residence Inn by Marriott New York Long Island East End
See all 4,311 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?
From just . 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 holiday package. It’s as easy as that! From flights and hotels to tours and rental cars, Expedia makes travelling 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 holiday?
Smart travellers 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 holiday 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 holiday 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

Image for Sparkling Pointe

Sparkling Pointe

You can enjoy a tasting or tour at Sparkling Pointe during your travels to Southold. Discover the sunsets and wineries in this family-friendly area.

Sparkling Pointe
Image for Croteaux Vineyards

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
Image for Sannino's Bella Vita Vineyard

Sannino's Bella Vita Vineyard

You can enjoy a tasting or tour at Sannino's Bella Vita Vineyard during your travels to Southold. Wander the beaches or discover the sunsets in this family-friendly area.

Sannino's Bella Vita Vineyard

What to do in Southold

Image for Sagaponack Sunset Electric Bike Tour

Sagaponack Sunset Electric Bike Tour

NZ$243
Per adult
Sagaponack Sunset Electric Bike Tour
Image for Private Hamptons Tour with Outlet Center Shopping

Private Hamptons Tour with Outlet Center Shopping

NZ$1,945
Per adult
Private Hamptons Tour with Outlet Center Shopping
See all activities in Southold

More holiday ideas

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