Southold Holidays

  • Plan, book, travel with confidence
    • payments icon
    Better together
    Save up to €185 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

Top Flight + Hotel Deals in Southold

Price found within the past 48 hours. Click for updated prices.
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Save 100% on your flight
per person
25 Jan - 29 Jan
found 13 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8.8/10 Excellent! (1,123 reviews)
I received exceptional service and truly felt cared for and respected. The level of compassion shown by the staff at Lotte Palace was beyond anything I have experienced before. Thank you to the team for their remarkable dedication. With many staff members having 20 to 40 years of service, I can see why this place stands out.

Reviewed on 12 Nov 2024

The Dominick

The Dominick

5 out of 5
Manhattan
Save 100% on your flight
per person
10 Feb - 16 Feb
found 19 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (1,005 reviews)
Unfortunately we paid 50 dollars a day for hotel fee but we weren’t allowed to use the sauna

Reviewed on 17 Nov 2024

Maison Rouge NYC

Maison Rouge NYC

2 out of 5
Manhattan
Save 100% on your flight
per person
11 Feb - 14 Feb
found 23 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
No reviews
The New York EDITION

The New York EDITION

5 out of 5
Manhattan
per person
27 Dec - 31 Dec
found 18 hours ago
Return flight included
Shannon (SNN) to New York (JFK)
9/10 Wonderful! (414 reviews)
For the price I just cannot accept that you don’t get an in room coffee machine. They offer free coffee in lobby up to 10:30am, but I hate having to trek down first thing in the morning. Hat to also call to get shower gel as there were no extras in the room. Check in took 15 mins. Room was ok for the price. Service was good.

Reviewed on 20 Oct 2024

Life Hotel New York

Life Hotel New York

3.5 out of 5
Manhattan
per person
27 Dec - 31 Dec
found 18 hours ago
Return flight included
Shannon (SNN) to New York (JFK)
8.4/10 Very Good! (1,000 reviews)
Great place to stay. Room was clean. Convenient.

Reviewed on 24 Nov 2024

Top hotels in Southold

The Shoals Suites and Slips
The Shoals Suites and Slips
3.5 out of 5
61600 Main Rd, Southold, NY
The price is €198 per night from 22 Dec to 23 Dec
€198
includes taxes & fees
22 Dec - 23 Dec
9.4/10 Exceptional! (131 reviews)
"The Shoals is really such a cute place. The rooms are spacious and very clean. My sisters and I stayed here for the second time in November. Last time I stayed during the week and it was very quiet. However this time we had someone staying next to us and you can hear the TV like it’s in your room ..."

Reviewed on 21 Nov 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 €84 per night from 8 Dec to 9 Dec
€84
includes taxes & fees
8 Dec - 9 Dec
7.4/10 Good! (1,001 reviews)
"Kind staffs!"

Reviewed on 12 Nov 2024

Quality Inn Old Saybrook - Westbrook
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 €76 per night from 26 Nov to 27 Nov
€76
includes taxes & fees
26 Nov - 27 Nov
7.6/10 Good! (892 reviews)
"Everything was satisfactory"

Reviewed on 15 Nov 2024

Pier Blue Inn Old Saybrook - Essex
See all 4,262 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 €1,034. 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

Corey Creek Winery

You can enjoy a tasting or tour at Corey Creek Winery during your travels to Southold. Wander the beautiful beaches in this family-friendly area.

Corey Creek Winery

Mattebella Vineyards

You can enjoy a tasting or tour at Mattebella Vineyards during your travels to Southold. Wander the beautiful beaches in this family-friendly area.

Mattebella Vineyards

Horton Point Park

Explore the great outdoors at Horton Point Park, a lovely green space in Southold. Wander the beaches or discover the sunsets in this family-friendly area.

Horton Point Park

What to do in Southold

The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

€167
Per adult
76% of travellers recommend
The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC
See all activities in Southold
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.