Southold Vacations from $758
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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.
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.
Corey Creek Winery
9.6/10 (5 reviews)
This boutique North Fork vineyard crafts innovative wines like White Cabernet Franc using indigenous yeasts. Savor sustainable vintages on their elevated deck with bay views while enjoying live music and lawn games.
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.
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.
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
$345 nightly
$391 total
Sep 9 - Sep 10
Total with taxes and fees
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
$83 nightly
$95 total
Aug 27 - Aug 28
Total with taxes and fees
8/10 Very Good! (1,001 reviews)
"Spider in my bed . Key didn’t work couldn’t get my things and refrigerator was full of my food"
Reviewed on Aug 25, 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
$323 nightly
$369 total
Sep 15 - Sep 16
Total with taxes and fees
8.4/10 Very Good! (705 reviews)
"The hotel was lovely and right on the Long Island Sound. The view was great. The room was comfortable. For the price you will pay per night, there should have been more added touches. They should provide robes and extra towels, etc. Upon check in, no one greeted us warmly or assisted in telling us ..."
Reviewed on Aug 26, 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.
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
How much does a Southold vacation package cost?
You can snap up a vacation package to this top destination from $758 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, October and December are the best times to look for cheap Southold vacation packages. Traveling in quieter months means you can usually find lower prices on accommodations and flights.
How many days is enough for Southold?
Dedicate around 3 days for your Southold vacation to discover everything that makes this place special. Explore key areas, including Greenport West and Pipes Cove. Then make a beeline for top attractions like Sannino's Bella Vita Vineyard and Corey Creek Winery. With a well-organized itinerary, you can keep busy with room for some me-time too. Want to travel beyond Southold? Consider squeezing in 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 travel dates: The things you'd like to do in Southold and your favorite season can help you decide when to go.
- Set a budget: Consider expenses like flights, meals and transportation when working out how much to save for your trip to Southold. Then, pick a hotel that fits your budget, whether that's an affordable stay or a deluxe getaway.
- Organize your Southold getaway with our trip planning tool: Search for and book hotels and things to do all in one place. You can also collaborate with friends and family to plan an unforgettable trip to Southold together.
- Decide how many days away: Start by making a list of all the attractions you want to get to in Southold. Then, estimate how long you'll need at each, including any travel time.
- Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to pick a Southold vacation package that brings all your bookings together.
- Book any day trips or activities: Now to the fun part — organizing everything you want to do and see. Check out some of the incredible things to do in Southold in Southold and book your tickets early to save time (and maybe some cash too!).
Does Expedia offer Book Now, Pay Later Southold vacation packages?
Your Southold trip should be an escape from your daily routine, not a reason for money worries. So to give you more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.
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- Raphael Winery
- Shinnecock Nation Cultural Center and Museum
- Noyac Golf Club
- Mattebella Vineyards
- Pugliese Vineyards
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- Visit Sag Harbor
- Elizabeth A. Morton National Wildlife Refuge
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- Where to stay in Southold
- Shelter Island Vacations
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- Wolffer Estates Vineyard
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- Cooper's Beach
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
