Southold Holidays from AU$2,971
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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.
NobleDEN Hotel
Manhattan
AU$3,759
per person
19 Nov - 26 Nov
found 1 day ago
Return direct flight included
Melbourne (MEL) to New York (JFK)
9.6/10 Exceptional! (1,661 reviews)
Comfortable, clean hotel in Little Italy. Nothing special, but does the job for solo and business travelers. It does have a rooftop deck with great views of the city, especially at night.
Reviewed on 14 Oct 2026
Southold Holiday
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
The Shoals Suites and Slips
61600 Main Rd Southold NY
AU$340
3 Nov - 4 Nov
includes taxes & fees
9.4/10 Exceptional! (345 reviews)
"Very clean property, beautiful view, and quiet."
Reviewed on 11 Oct 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
AU$319
2 Nov - 3 Nov
includes taxes & fees
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundable
AU$127
19 Oct - 20 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.
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.
The Old Field Vineyards
9.6/10 (5 reviews)
This family-owned vineyard, Long Island's oldest continuously operated winery, offers handcrafted wines in a rustic setting. Enjoy tastings on expansive lawns overlooking Southold Bay.
Custer Institute and Observatory
Long Island's oldest public observatory invites you to explore the cosmos through powerful telescopes every Saturday night. Enjoy guided stargazing at this historic astronomical sanctuary established in 1927.
McCabe's Beach
Why not spend a lazy afternoon at McCabe's Beach during your trip to Southold? Stroll along the beaches or discover the area's sunsets.
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.
What to do in Southold
Full Day Private Long Island Wine Tours from New York City
AU$265
per adult
Frequently asked questions
How much does a Southold holiday package cost?
You can snap up a holiday package to this top destination from AU$2,971 on Expedia. However, how much your holiday to Southold costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Southold?
January, February and March are great times to look for cheap Southold holiday packages. Choosing to travel in quieter months means you can generally find better prices on flights and hotels.
How many days is enough for Southold?
Dedicate at least 3 days for your Southold holiday to immerse yourself in everything that makes this place unique. Explore popular areas, including Greenport West and Pipes Cove. Then head to the major sights like Osprey's Dominion and Croteaux Vineyards. With a good itinerary, you can keep busy with room for some me-time too. Want to travel beyond Southold? Consider an excursion or two.
How to find the best Southold package deals?
Bagging a cheap Southold package deal is a cinch with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can tweak your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Southold package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Southold holiday as a package?
An Expedia holiday package could score you significant savings when compared to booking flights and hotels individually. Better still, you can personalise your Southold escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Southold?
If you're planning a spur-of-the-moment Southold holiday, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Southold?
- Choose your dates: The things you'd like to do in Southold and your favourite season can help you decide when to travel.
- Work out your budget: Ensure you have enough money to pay for everything from transportation and meals to flights and experiences. Your accommodation will likely be the largest expense during your trip to Southold.
- Decide how long to go for: Now that you know more about Southold, you can work out the perfect length of your break. Put together a rough itinerary and allocate enough time to cover everything you want to do.
- Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a customised Southold holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
