Southold Vacations from $863
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Your Southold Vacation
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 customized Southold vacation 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 vacation on Expedia.
The Latest Southold vacation packages
Price found within the past 48 hours. Click for updated prices.
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.
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.
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.
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.
What to do in Southold
Full Day Private Long Island Wine Tours from New York City
$189
per adult
Southold Hotel Deals
The Shoals Suites and Slips
61600 Main Rd Southold NY
$267 nightly
$302 total
Nov 1 - Nov 2
Total with taxes and 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 Sep 30, 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
$217 nightly
$249 total
Nov 10 - Nov 11
Total with taxes and fees
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundable
$86 nightly
$99 total
Oct 20 - Oct 21
Total with taxes and 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.
Find the Best Southold Vacation Packages
Southold Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Tweed - New Haven Regional Airport (HVN) |
Population | 5,700 |
Max Temp Winter | 40ºF |
Max Temp Summer | 75ºF |
Top Sights | Wolffer Estates Vineyard, 67 Steps Beach and Macari Vineyards |
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Frequently asked questions
What's included in a Southold vacation package?
A Southold vacation package typically bundles round-trip flights, your hotel stay, and often a rental car. As a beach destination, the area's many hotels offer convenient access to the coast, and about half of package hotels feature ocean views. Many properties also provide amenities like free breakfast and free WiFi, and you can often add airport transfers to and from New York, NY (JFK-John F. Kennedy Intl.) to your booking.
How can I save money on a Southold vacation package?
When you bundle, you can save up to 30%*. To save money on a Southold package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What's the best vacation package for Southold?
For couples seeking the best vacation packages in Southold, a stay at Vine & Sand is a strong choice. Rated 9.4 out of 10, this property offers an outdoor pool and free breakfast, and travelers frequently highlight its well-maintained grounds, lovely rooms, and beautiful breakfast.Families planning a Southold vacation package might consider The Shoals Suites and Slips. This 3.5-star property, rated 9.5 out of 10, features family rooms, free breakfast, and a restaurant, and travelers praise its super clean rooms and excellent overall experience.
Is Southold better suited for a beach vacation or a cultural trip?
Southold is primarily a beach destination, making it ideal for a relaxing coastal escape. About half of the package hotels in Southold offer ocean views, enhancing the beach experience. Travelers can enjoy the sands of The Hamptons Beaches about 7 miles from central Southold, or the more local Horton Lane Beach about 3 miles away.While a Southold vacation focuses on its scenic coastline, the area also has a rich history. It was the first English settlement in New York State, founded by Puritans in 1640. Visitors can explore the Southold Historic District, which features many older structures added to the National Register of Historic Places in 1997. The region is also known for its numerous wineries, such as Peconic Bay Winery about 6 miles from central Southold, offering a different kind of cultural experience. This blend allows for a beach-focused trip with opportunities to delve into local history and wine culture.
What's included in a Southold beach vacation package?
Southold beach vacation packages combine flights with a hotel stay, providing a convenient way to experience this beach destination. Many hotels, such as The Shoals Suites and Slips, a 3.5-star property rated 9.5 out of 10, offer amenities like a restaurant and family rooms, providing a comfortable base for your trip. Another excellent choice is Vine & Sand, rated 9.4 out of 10, which features an outdoor pool and free breakfast. About half of the package hotels in Southold also provide ocean views, enhancing your coastal getaway. These Southold vacation packages allow you to customize your trip around the area's beaches and local attractions.
What are the top things to do in Southold?
A Southold vacation offers a variety of experiences, from relaxing on the sand to exploring local vineyards:Browse and book things to do in Southold on Expedia.
Do you need to rent a car in Southold, or is public transport enough?
For a Southold vacation package, renting a car offers the most flexibility to explore the area. While some hotels are centrally located, many of Southold's attractions, including its numerous wineries like Sparkling Pointe about 2 miles from central Southold and Raphael Winery about 4 miles away, are spread out.A car is also practical for reaching the destination from major airports like New York, NY (JFK-John F. Kennedy Intl.), which is about 75 miles from central Southold. For Southold vacation packages with flights, having your own vehicle allows you to easily visit different beaches, vineyards, and other points of interest, making it ideal for a Southold beach vacation package.
Are Southold vacation package hotels conveniently located?
Southold vacation package hotels are generally conveniently located, with many properties situated close to the town center.For example, Vine & Sand is about 1 mile from central Southold, offering easy access to local attractions. Similarly, The Shoals Suites and Slips, a 3.5-star property, is also about 1 mile from central Southold.Staying in these central locations allows travelers to explore Southold's charm and nearby points of interest with ease.
Can I change or cancel my Southold vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Southold vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Southold vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Southold vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Southold?
To find last-minute vacation packages to Southold, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Southold vacation packages?
Free cancellation on a Southold vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Southold vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Southold getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Southold vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.
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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.
