Southold Holidays from AU$1,417

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Your Southold Holiday

The coastal scenery and rich history are just the beginning of the things Southold has to offer. Discover the best of this captivating city your way with a personalised Southold holiday package. If taking in sights is part of the programme during your trip to Southold, swing by leading attractions like 67 Steps Beach, Pindar Vineyards and Kontokosta Winery. Don't put off your visit to this city any longer. Your dream Southold holiday is just a few clicks away with Expedia.

The Latest Southold Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Arlo SoHo

Arlo SoHo

4 out of 5
Manhattan
Save 100% on your flight
per person
23 Jul - 29 Jul
found 10 hours ago
Return direct flight included
Toronto (YYZ) to New York (JFK)
8.8/10 Excellent! (1,308 reviews)
This property was extremely nice. All staff was very helpful and gave great recommendations for dining. The rooftop var was a real treat as well!

Reviewed on 12 Jun. 2024

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Save 100% on your flight
per person
23 Jul - 29 Jul
found 10 hours ago
Return direct flight included
Toronto (YYZ) to New York (JFK)
8.8/10 Excellent! (1,007 reviews)
Great service-middle of action

Reviewed on 13 Jun. 2024

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
per person
18 Aug - 25 Aug
found 8 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.2/10 Wonderful! (547 reviews)
Smart hotel superbly located

Reviewed on 12 Jun. 2024

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
per person
31 Jul - 7 Aug
found 12 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.8/10 Exceptional! (1,011 reviews)
The staff went above and beyond when my flight was cxld. due to weather, helping with arrangements for cars, luggage and other items needed

Reviewed on 12 Jun. 2024

Holiday Inn Express - New York City Chelsea, an IHG Hotel

Holiday Inn Express - New York City Chelsea, an IHG Hotel

3 out of 5
Manhattan
Save 100% on your flight
per person
23 Jul - 29 Jul
found 10 hours ago
Return direct flight included
Toronto (YYZ) to New York (JFK)
8/10 Very Good! (1,004 reviews)
Property was walking distance from many of the train stations. We walked to time square and it was not bad. The breakfast was okay. I wished they would’ve changed it up from day to day. They have bikes you can rent but the deposit is kinda high so we walked most of the time. Quite a distance from the airport tho. About 40 mins with light traffic. Overall, I would stay here again..

Reviewed on 14 Jun. 2024

Southold Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)
Population
5,700
Max Temp Winter
4ºC
Max Temp Summer
24ºC
Top Sights
67 Steps Beach, Macari Vineyards and Pindar Vineyards

Our pick of the best Southold Hotel Deals

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 AU$178 per night from 30 Jun to 1 Jul
AU$178
per night
30 Jun - 1 Jul
5.8/10 (368 reviews)
"We arrived before check in time, staff worked with us to get room ready. They were very nice"

Reviewed on 10 Jun. 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 AU$572 per night from 25 Jun to 26 Jun
AU$572
per night
25 Jun - 26 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 AU$409 per night from 15 Jul to 16 Jul
AU$409
per night
15 Jul - 16 Jul
9.2/10 Wonderful! (82 reviews)
"Beautiful hotel, everything brand new everything clean staff very friendly and accommodating close to everything"

Reviewed on 11 Jun. 2024

The Bentley Hotel Southampton
See all 4,371 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Southold holiday package cost?
From just AU$1,417. 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 Long Island Full Day Wine and Food Tasting Vineyard Tour from NYC

Long Island Full Day Wine and Food Tasting Vineyard Tour from NYC

AU$233
Per adult
Long Island Full Day Wine and Food Tasting Vineyard Tour from NYC
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.