Southold Holidays from £1,087

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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.
Archer Hotel Florham Park/Morristown

Archer Hotel Florham Park/Morristown

4 out of 5
Price was £1,777, price is now £1,087 per person
£1,087
per person
22 Dec - 26 Dec
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
9.4/10 Exceptional! (1,006 reviews)

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Save 100% on your flight
Price was £3,621, price is now £1,925 per person
£1,925
per person
12 Jan - 17 Jan
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (293 reviews)

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was £2,825, price is now £1,611 per person
£1,611
per person
14 Jan - 21 Jan
found 6 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (1,004 reviews)

Le Meridien New York, Central Park by Marriott

Le Meridien New York, Central Park by Marriott

4 out of 5
Manhattan
Price was £2,194, price is now £1,323 per person
£1,323
per person
22 Dec - 26 Dec
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
8/10 Very good! (1,001 reviews)
The hotel was great and will stay there again. The staff was friendly and the rooms were clean. The location was great to get to Central Park and an easy walk to the theater distract and Times Square. The roof top bar/restuarant is beautiful and a great spot to end the evening. On the downside, the rooms are small but enough room for 2 people and the drawer space is limited.

Reviewed on 23 Oct 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was £2,501, price is now £1,518 per person
£1,518
per person
23 Dec - 28 Dec
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)
A beautiful hotel in a prime location with an excellent helpful staff...

Reviewed on 2 Nov 2026

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 £159 per night from 10 Nov to 11 Nov
£159
10 Nov - 11 Nov
includes taxes & fees
The Shoals Suites and Slips
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is £163 per night from 3 Dec to 4 Dec
£163
3 Dec - 4 Dec
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"NA"

Reviewed on 2 Nov 2026

Water's Edge Resort & Spa
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 £67 per night from 17 Nov to 18 Nov
£67
17 Nov - 18 Nov
includes taxes & fees
Pier Blue Inn Old Saybrook - Essex
See all 4,290 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

Stay near popular Southold attractions

Sparkling Pointe

8.8/10 (11 reviews)
Sparkling Pointe crafts exquisite sparkling wines using traditional Méthode Champenoise in their Southold vineyard. Savour their diverse bubblies in an elegant tasting room with vineyard views.
See properties

What to do in Southold

great fun with friends

Full Day Private Long Island Wine Tours from New York City

£141
per adult
Full Day Private Long Island Wine Tours from New York City
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.

Explore a world of travel with Expedia

* 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.