Southold Vacations from AED3,557
Book a Hotel + Flight together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to AED 5,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Southold Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Log Comfort 3
Lower Vailsburg
AED3,557
per person
Nov 22 - Nov 29
found 15 hours ago
Roundtrip non-stop flight included
Manchester (MAN) to New York (JFK)
8/10 Very Good! (1 review)
The host was wonderful and very responsive. She even offers extended check out which was great. The listing could be a bit more detailed on the apartment. It appears to be a place to rent rooms but the whole apartment was offered. There is a camera IN the apartment which was very uncomfortable as I felt like I could not get comfortable for the time I was there and being watched I could not enjoy the living room. Other than that I have no complaints.
Reviewed on 3 August 2026
Ink 48 Hotel
Manhattan
AED5,447
per person
Nov 22 - Nov 29
found 15 hours ago
Roundtrip non-stop flight included
Manchester (MAN) to New York (JFK)
8.4/10 Very Good! (1,768 reviews)
Hotel was great, quick and rather safe walk to Time square or a Subway station. Would absolutely stay again.
Reviewed on 29 September 2026
Find the Best Southold Vacation Packages
Southold Hotel Deals
The Shoals Suites and Slips
61600 Main Rd Southold NY
AED 741
AED 939 total
1 Oct - 2 Oct
includes taxes & fees
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
AED 287
AED 330 total
1 Oct - 2 Oct
includes taxes & fees
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
AED 658
AED 821 total
4 Oct - 5 Oct
includes taxes & fees
8.8/10 Excellent! (1,012 reviews)
"Front desk helpful! Indoor bar area nice area for single traveler plenty of space."
Reviewed on 28 September 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. Savor 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. Savor 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 personalized 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 personalized 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 artifacts. 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.
Frequently asked questions
How much does a Southold vacation package cost?
Offering great value package deals from AED3,557 on Expedia, you'll be pleasantly surprised at how much a vacation to Southold costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Southold?
January, February and March are great times to look for cheap Southold vacation packages. Choosing to travel in less busy periods means you can generally find reduced prices on flights and hotels.
How to find the best Southold package deals?
Begin your search for a Southold package deal by entering your destination and preferred trip dates under our "Packages" tab. Then select some filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Southold package deal straight away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Southold getaway off to a flying start.
Is it cheaper to book a Southold vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll generally land a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Southold vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Southold?
If you've got your Southold travel dates locked in, book early to bag some unbeatable deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Southold?
- Choose the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Southold.
- Set a budget: Consider expenses such as flights, food and transportation when calculating how much to save for your trip to Southold. Then, pick a property that works with your budget, whether that's an affordable stay or a more upscale getaway.
- Set the duration of your trip: Start by listing all the attractions and activities you'd like to get to in Southold. Then, estimate how long you'll need at each, along with any travel time.
- Bundle your accommodations and airfare: Once you've settled on your trip dates and duration, book the perfect Southold vacation package for you.
