Southold Vacations from ￥380,768
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The Latest Southold Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Beacon
Manhattan
￥432,700
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
9.4/10 Exceptional! (1,506 reviews)
Great hotel and location. We came for the wiggles concert and it was right outside our door. Rooms are so quiet. I was worried right across from the elevator but I heard nothing ! Staff is ultra friendly. You can tell they care a lot about the hotel and appearance. The bed was a little soft for me but that’s a preference thing.
Reviewed on Aug 25, 2026
Find the Best Southold Vacation Packages
Southold Hotel Deals
The Shoals Suites and Slips
61600 Main Rd Southold NY
￥46,221
￥56,783 total
Sep 2 - Sep 3
includes taxes & fees
9.4/10 Exceptional! (326 reviews)
"Beautiful spacious rooms with great rocking chairs on the balcony with a water view. Property was immaculate. Lovely continental breakfast. Great outdoor food truck for a snack and adult beverage!"
Reviewed on Aug 25, 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
￥13,857
￥15,936 total
Aug 26 - Aug 27
includes taxes & fees
8/10 Very Good! (1,017 reviews)
"Needs to be updated badly. Would have spent more money to stay somewhere better."
Reviewed on Aug 23, 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
￥36,269
￥55,058 total
Sep 15 - Sep 16
includes taxes & fees
8.4/10 Very Good! (703 reviews)
"The property is well maintained and the location is perfect, however, there were some downsides during our stay. My fiancé, our dog, and I went to this hotel as it's a pet-friendly location, on their website they advertised amenities for pets (i.e, Yeti dog bowl(s), plush bed) but we never received ..."
Reviewed on Aug 24, 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.
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.
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.
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.
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.
What to do in Southold
Full Day Private Long Island Wine Tours from New York City
￥30,166
per adult
Frequently asked questions
How much does a Southold vacation package cost?
You can snap up a vacation package to this top destination from ￥380,768 on Expedia. However, how much your vacation 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 vacation 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 vacation 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 vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and hotels individually. Better still, you can personalize 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 vacation package to Southold?
If you're planning a spur-of-the-moment Southold vacation, 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 favorite 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 accommodations 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 customized Southold vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
