Southold Holidays from NZ$2,735
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The Latest Southold Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Park Ave NYC
Manhattan
NZ$2,735
per person
22 Nov - 29 Nov
found 9 hours ago
Return direct flight included
London (LGW) to New York (JFK)
9/10 Wonderful! (1,778 reviews)
Great hotel experience overall. The location was perfect for a tourist and not too hectic like other parts of NYC. The hotel has a very cool bar and terrace. The rooms were clean and included thoughtful complimentary things. Staff were super nice and helpful. Will definitely stay there again!
Reviewed on 29 Sept 2026
Ink 48 Hotel
Manhattan
NZ$3,753
per person
9 Nov - 15 Nov
found 8 hours ago
Return flight included
Auckland (AKL) to New York (JFK)
8.4/10 Very good! (1,768 reviews)
We had a great stay at Ink 48 in New York City. The hotel has a really cool, modern atmosphere, and the staff was friendly and helpful throughout our stay. Our room was comfortable, clean, and spacious, especially for a New York City hotel.
One of the best things about Ink 48 is the location. It's close enough to everything we wanted to do in Manhattan while being just far enough away from the busiest areas to feel a little more relaxed. The rooftop views are also fantastic—you get an incredible view of the Manhattan skyline and the Hudson River.
Overall, we really enjoyed our stay and would definitely consider staying at Ink 48 again. Great location, comfortable rooms, friendly service, and some of the best views in the city. Highly recommended!
Reviewed on 2 Oct 2026
Southold Holiday
Our pick of the best Southold Hotel Deals
The Shoals Suites and Slips
61600 Main Rd Southold NY
NZ$456
1 Nov - 2 Nov
includes taxes & fees
9.4/10 Exceptional! (344 reviews)
"The staff were all great, the food from food truck was delicious, check in was quick!"
Reviewed on 30 Sept 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
NZ$160
5 Oct - 6 Oct
includes taxes & fees
8/10 Very good! (1,002 reviews)
"Nice place !"
Reviewed on 1 Oct 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
NZ$351
4 Oct - 5 Oct
includes taxes & fees
8.8/10 Excellent! (1,014 reviews)
"They upgraded us to a balcony and there was a lot to do there. The pool and hot tub were nice too!"
Reviewed on 1 Oct 2026
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.
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.
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.
What to do in Southold
Full Day Private Long Island Wine Tours from New York City
NZ$330
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 NZ$2,735 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.
