Southold Holidays from £1,015
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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.
LGA AIRPORT
Queens
£3,990
per person
21 Oct - 26 Oct
found 23 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
10/10 Exceptional! (2 reviews)
The best airbnb Ive stayed at in New York with the best price for our family of 6. The place was so clean, amenities looked brand new. It had a homey feel to it, my kids didnt want to leave. We will definently be booking again in the future.
Reviewed on 24 Dec 2025
Hotel St. James
Manhattan
£1,076
per person
21 Oct - 26 Oct
found 23 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
8.8/10 Excellent! (7,930 reviews)
Great location. Budget hotel. Noisy air conditioning. Son’s room had broken blind. No tea or coffee making facilities. Hotel in need of TLC. However, comfy beds and pillows so if you are looking for bed in great location, hotel is fine. If you want hotel with amenities, this is not the one.
Reviewed on 18 Sept 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
61600 Main Rd Southold NY
£191
1 Oct - 2 Oct
includes taxes & fees
9.4/10 Exceptional! (339 reviews)
"Our stay was filled with quietness set in a backdrop of beautiful blue skies enveloping the peconic bay. What a great place to come apart and forget about the stress of the week, relax and unwind. My husband and I were pleased with our stay. Everyone was ao friendly and helpful Mario was very attentive ..."
Reviewed on 14 Sept 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
£70
22 Sept - 23 Sept
includes taxes & fees
8/10 Very good! (1,003 reviews)
"Staff was helpful and professional. Room was clean, basic, nice. The TV was a little sketchy-some stations were static. The bathroom shower was great: good flow, hot and soothing. Overall, very good for the price."
Reviewed on 17 Sept 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
£230
5 Oct - 6 Oct
includes taxes & fees
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.
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.
Croteaux Vineyards
10.0/10 (12 reviews)
America's only all-rosé vineyard offers a taste of Provence in New York's North Fork. Savour wine flights in the picturesque garden setting, complete with rustic barn and seaside charm.
Sannino's Bella Vita Vineyard
9.6/10 (4 reviews)
This intimate vineyard offers personalised expert-guided wine tastings amid sustainable vineyards. Experience their unique White Merlot overlooking scenic North Fork landscapes or stay at their on-site B&B.
Horton Point Park
9.4/10 (3 reviews)
This 1857 lighthouse stands sentinel over Long Island Sound, housing a nautical museum filled with maritime artefacts. Climb to the top for panoramic views, then follow the nature trail to the peaceful rocky beach below.
Horton Lane Beach
9.0/10 (4 reviews)
This rocky shoreline along Long Island Sound offers peaceful views beside the historic Horton Point Lighthouse. Explore maritime heritage at the adjacent Nautical Museum, open seasonally.
Osprey's Dominion
9.6/10 (5 reviews)
This award-winning North Fork winery showcases sustainable viticulture through distinctive Sauvignon Blanc and Merlot offerings. Enjoy tastings on their spacious lawn with weekend live music and picnic areas.
Mattebella Vineyards
8.0/10 (4 reviews)
This family-run vineyard crafts sustainable wines in an intimate North Fork setting. Enjoy personalised tastings with garden-to-table pairings on the patio overlooking lush vines.
Corey Creek Winery
9.6/10 (5 reviews)
This boutique North Fork vineyard crafts innovative wines like White Cabernet Franc using indigenous yeasts. Savour sustainable vintages on their elevated deck with bay views while enjoying live music and lawn games.
What to do in Southold
Full Day Private Long Island Wine Tours from New York City
£139
per adult
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.
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* 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.
