Southold Holidays from £1,127

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Your Southold Holiday

The coastal scenery and rich history are just the beginning of the things Southold has going for it. Experience the very best of this interesting city your way with a customised Southold holiday package. 67 Steps Beach, Raphael Winery and Railroad Museum of Long Island are just some of the many sights worth checking out during your trip to Southold. A few quick clicks is all it takes to put together your ideal Southold holiday on Expedia.

Top Southold Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
per person
14 Sept - 21 Sept
found 22 hours ago
Return flight included
London (LGW) to New York (JFK)
8.4/10 Very Good! (532 reviews)
We stayed here for an overnight for a girls trip with my 8yr old daughter, we had the best time. We will be back!

Reviewed on 30 Jul 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
3 Sept - 10 Sept
found 4 hours ago
Return flight included
London (LGW) to New York (JFK)
8.8/10 Excellent! (1,006 reviews)
Nice views.. but food at restaurant left a lot to be desired. Also staff presentation was terrible. They need uniforms and a dress code. Booty shorts, wrinkled clothing... its all a part of the experience and everyone looked like they got up out of bed and came to work. Take pride. Its managements fault ..

Reviewed on 30 Jul 2025

The Pierre, A Taj Hotel, New York

The Pierre, A Taj Hotel, New York

5 out of 5
Manhattan
Save 100% on your flight
per person
9 Sept - 14 Sept
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
9.2/10 Wonderful! (1,000 reviews)
Staff went out of their way to be courteous and polite

Reviewed on 30 Jul 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
per person
10 Oct - 14 Oct
found 1 day ago
Return flight included
London (LGW) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
Exceedingly above my expectations

Reviewed on 31 Jul 2025

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Save 100% on your flight
per person
17 Oct - 21 Oct
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
9.2/10 Wonderful! (617 reviews)
We loved our stay at the Lotte Towers! The rooms were very spacious for our family of 4. We were provided a fridge on request. The views were amazing. The lifts were quick to get us to the 58th floor! Our rooms were serviced twice daily. Cannot fault anything at Lotte would love to return one day!!

Reviewed on 15 Apr 2025

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 Kontokosta Winery

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 £331 per night from 3 Aug to 4 Aug
£331
3 Aug - 4 Aug
includes taxes & fees
9.4/10 Exceptional! (187 reviews)
Already Want to Return
"The property is beautiful- was nice to relax in the Adirondack chairs near the marina in the evenings. We stayed in the Grand Suite and everything was spotless and comfortable. As others have said, it is a bit easy to hear your neighbors through the walls at night, but nothing earplugs can’t fix ..."

Reviewed on 31 Jul 2025

The Shoals Suites and Slips
Vine & Sand

Vine & Sand

3 out of 5
47100 New York 25, Southold, NY
10/10 Exceptional! (8 reviews)
"Beautiful house and trip to stay in the North Fork. Hosts are incredible. Highly recommend!!"

Reviewed on 23 Jul 2025

Get rates
Vine & Sand
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 £96 per night from 10 Aug to 11 Aug
£96
10 Aug - 11 Aug
includes taxes & fees
7.6/10 Good! (1,015 reviews)
"This hotel is modern and provides as close to a full breakfast as you could get under the heading of "continental". The room was spacious and clean. My one complain was the overall design of the building. First, like us, everyone had to drive around both sides of the building to find the office which ..."

Reviewed on 27 Jul 2025

Quality Inn Old Saybrook - Westbrook
See all 4,346 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
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

What to do in Southold

Join a small group full-day wine tour with a certified Sommelier host

Long Island Wine and Food Day Trip with Sommelier host from NYC

£117
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting

From Mattituck: North Fork Area Bike Tour with Food Tasting

£101
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
See all activities in Southold

Frequently asked questions

Why should I book my Southold holiday with Expedia?
Expedia has your back for every aspect of your Southold getaway. You'll always land the best prices, but when you bundle your accommodation, flights and/or car hire into a holiday package, you'll score even bigger savings. Looking to really make the most of your escape? Add a few fun activities and tours to your package. We offer flexible cancellation policies on most bookings, so you won't need to worry if you have to change your plans. Visit our Customer Service Portal link to learn more.
When is the best time of year to holiday in Southold?
May, June and July are the busiest months in Southold, while January, October and December are generally a lot quieter. Plan your visit to Southold according to what style of adventure you're looking for. January is the coolest time of year, when daytime temperatures average 1ºC. In August, the warmest month, you will experience averages of 23ºC during the day.
What is the top hotel for my holiday in Southold?
Shorewood Inn is the perfect base for a memorable adventure in Southold, offering all the conveniences you need.
How do I get a cheap holiday to Southold?
Combine your bookings with Expedia to save on your next trip. With more than 400 partner airlines and 321,000 hotel options across the world, your Southold holiday can be tailored exactly to suit your budget. With all that extra money, why not throw in one or more fun tours and experiences? It's an easy way to unlock even more bargains. Your dream holiday in Southold is closer than you thought! Learn more about how you can save money on your holiday when you book a flight and hotel together with Expedia.
What should I do on my Southold holiday?
Ensure your holiday in Southold is a memorable one by exploring its major attractions. 67 Steps Beach, Macari Vineyards, Pindar Vineyards and Kontokosta Winery are just a few of the things to put on your itinerary while you're in the area.
Do I need a visa for my Southold holiday?
Official government websites have all the information you need on visa requirements, application procedures and any supporting documentation. Your nationality and the purpose of your visit, whether it be for holidays or business, will determine if you need a visa for Southold. Also be sure that your passport is up to date and has at least six months validity remaining after your intended return date. Do all your travel planning ahead of time to avoid any last-minute surprises.
What should I wear on my Southold holiday?
Do a little research into the sorts of clothing people in Southold wear, and consider browsing social media fashion pages for inspiration. Whatever your look, try to create a versatile wardrobe full of pieces that suit your destination and show off your personal style.
What does an Expedia Southold holiday include?
It's up to you! Simply choose from a variety of Southold bundles, such as a hotel, hire car and flight. You can also book a flight and a hotel, or a car hire and a flight. Once you've made your booking, add on the fun stuff like experiences and activities. Whatever your Southold holiday looks like, you'll save! Discover an excellent range of property types and pick one that matches the size of your group. The most popular rentals here are private holiday homes and cottages. With Expedia, you can easily tailor your Southold escape any way you like.
Does Expedia offer Book Now, Pay Later Southold holidays?
Expedia has teamed up with online lender Klarna to make booking your next trip easier on your wallet. Paying in instalments means you can spread the costs of your next adventure, leaving you with more cash to play with while you're away. Klarna has several payment plans to choose from, so you're sure to find one that fits your budget. Browse these flexible payment options:

  • Pay monthly holidays: If paying across multiple transactions sounds right for you, Klarna offers just that! Paying in convenient monthly instalments will make your holiday dreams possible.
  • No-deposit holidays: Hitting the "book now" button is much easier with this payment option. With no deposit required for your escape, you can Book Now, Pay Later and start working on your travel itinerary.

Can I choose my airline with a Southold Expedia holiday?
With a holiday package, you're always in charge. Whether you want to fly to Southold in first class or coach, simply pick from the available airline options. Expedia has access to over 400 airline partners worldwide.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.