Southold 2024 Holidays

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Top hotels in Southold

Greenview Inn Riverhead
Greenview Inn Riverhead
2 out of 5
1433 W Main St, Riverhead, NY
Fully refundableReserve now, pay when you stay
The price is €108 per night from 16 Jun to 17 Jun
€108
per night
16 Jun - 17 Jun
5.8/10 (361 reviews)
Satisfied couple
"The inn was a great deal compared to other hotels in the area and room was updated and very clean and comfy."

Reviewed on 28 May 2024

Greenview 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 €331 per night from 23 Jun to 24 Jun
€331
per night
23 Jun - 24 Jun
9.4/10 Exceptional! (82 reviews)
"Lovely spot. Beautiful rooms and helpful staff. We will come again"

Reviewed on 31 May 2024

The Shoals Suites and Slips
The Bentley Hotel Southampton
The Bentley Hotel Southampton
2 out of 5
161 Hills Station Rd, Southampton, NY
Fully refundableReserve now, pay when you stay
The price is €194 per night from 23 Jun to 24 Jun
€194
per night
23 Jun - 24 Jun
9.2/10 Wonderful! (76 reviews)
"Large room recently updated, didn’t hear other guests"

Reviewed on 29 May 2024

The Bentley Hotel Southampton
See all 4,364 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.

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

More trip options

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