Southold Holidays from AU$2,678

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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.
Truss Hotel Times Square

Truss Hotel Times Square

4 out of 5
Manhattan
per person
9 Jul - 16 Jul
found 13 hours ago
Return flight included
Sydney (SYD) to New York (JFK)
8.2/10 Very Good! (1,451 reviews)
Clean rooms, friendly front desk staff. Thin walls, very noisy neighbors. Parking is not affiliated with the hotel.

Reviewed on 5 Jun. 2024

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
per person
16 Aug - 23 Aug
found 9 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
8.8/10 Excellent! (3,679 reviews)
I asked the front desk for ice at 10:30pm. They told me it was too late and that I needed to go to the bar to get some. Later I found out that there was an ice machine in the lounge in my floor (26th)! I notified the front desk that I had trouble charging my devices because there was only one available outlet in the room. There was an USB outlet by the bed, but it was controlled by the light switch, so when I shut the light, it stopped charging. I told them to send someone to take a look the next day while we were out. When we got to the room at 11pm,a technician was already working on it, so we could not go to sleep! He was not able to fix it. The next day it seemed like someone came to fix it. It worked for a little while only...

Reviewed on 5 Jun. 2024

Kimpton Hotel Eventi, an IHG Hotel

Kimpton Hotel Eventi, an IHG Hotel

4 out of 5
Manhattan
per person
16 Aug - 23 Aug
found 9 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9/10 Wonderful! (1,003 reviews)
The room is not clean properly. A lot of dust.

Reviewed on 2 Jun. 2024

Hyatt Herald Square New York

Hyatt Herald Square New York

4 out of 5
Manhattan
per person
16 Aug - 23 Aug
found 9 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
8.4/10 Very Good! (1,000 reviews)
Great visit and very close to MSG

Reviewed on 3 Jun. 2024

Hilton Garden Inn New York/Tribeca

Hilton Garden Inn New York/Tribeca

3 out of 5
Manhattan
per person
9 Jul - 16 Jul
found 13 hours ago
Return flight included
Sydney (SYD) to New York (JFK)
8.4/10 Very Good! (1,011 reviews)
This location just steps from the ACE trains. My only criticism was I was on the sixth floor and had to go all the way down to the third floor to find an ice machine that was working.

Reviewed on 3 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

Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex
2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is AU$136 per night from 10 Jun to 11 Jun
AU$136
per night
10 Jun - 11 Jun
7.6/10 Good! (789 reviews)
"Most of these reviews give less than 5 stars because it’s outdated, which it is, but other than that I love my stay. I had no issues. Front desk staff were super friendly. Coffee machine in the room which was nice. Great area and location too, a lot of restaurants in walking distance. They are in ..."

Reviewed on 5 Jun. 2024

Pier Blue Inn Old Saybrook - Essex
The Shoals Suites and Slips
The Shoals Suites and Slips
3.5 out of 5
61600 Main Rd, Southold, NY
The price is AU$634 per night from 23 Jun to 24 Jun
AU$634
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
Quality Inn Old Saybrook - Westbrook
Quality Inn Old Saybrook - Westbrook
2.5 out of 5
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is AU$174 per night from 12 Jun to 13 Jun
AU$174
per night
12 Jun - 13 Jun
7.4/10 Good! (966 reviews)
"Great hotel for the money, though it's a little off the beaten path (I had no idea where to find Old Saybrook from the hotel location). Still, it was perfect for my needs. They had a nice (free) continental breakfast and the pool area was great."

Reviewed on 28 May 2024

Quality Inn Old Saybrook - Westbrook
See all 4,362 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$2,678. 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
Image for Private Hamptons Tour with Outlet Center Shopping

Private Hamptons Tour with Outlet Center Shopping

AU$1,812
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.