Southold Trips (flight + hotel)

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Top hotels in Southold

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 P7,403 per night from 22 May to 23 May
P7,403
per night
22 May - 23 May
8.4/10 Very Good! (1,001 reviews)
"comfortable and courteous. Enjoyed the goodie bag we received when checking in."

Reviewed on May 10, 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 P16,976 per night from 20 May to 21 May
P16,976
per night
20 May - 21 May
9.4/10 Exceptional! (75 reviews)
"Would go back in a heartbeat. The staff were so friendly and the rooms are gorgeous. Honestly it’s a best kept secret and I’m so glad we found it!"

Reviewed on Apr 29, 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 P8,277 per night from 21 May to 22 May
P8,277
per night
21 May - 22 May
9/10 Wonderful! (768 reviews)
"Room size was perfect"

Reviewed on May 13, 2024

Residence Inn by Marriott New York Long Island East End
See all 4,328 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?
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 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.

Popular places to visit

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 Private Hamptons Tour with Outlet Center Shopping

Private Hamptons Tour with Outlet Center Shopping

P66,336
Per adult
Private Hamptons Tour with Outlet Center Shopping
See all activities in Southold

More trip options

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