Southold Vacations from $561

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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.
Ink 48 Hotel

Ink 48 Hotel

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $976, price is now $561 per person
$561
per person
Sep 17 - Sep 20
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (1,710 reviews)
.

Reviewed on Jul 10, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,842, price is now $1,000 per person
$1,000
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (3,130 reviews)
Excellent location near Times Square, and our family of five all loved the daily breakfast buffet!

Reviewed on Jul 11, 2026

Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,014, price is now $577 per person
$577
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.6/10 Excellent! (2,498 reviews)
We were very pleasantly surprised by how cool the hotel was! Entering, you realize that it is very stylish from the lobby area to the rooms. The room we rented was a large studio with a queen bed and a pull-out sofa. You could smell how clean it was upon entering the room. It is bare bones but that's exactly what we needed. It was so interesting that the shower was right there in the room and you could see that someone was in there but you couldn't see them. It worked great. The front desk staff recommended a local restaurant for us and it was amazing! No complaints whatsoever. I would highly recommend the hotel for anyone staying in the area.

Reviewed on Jul 9, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $2,684, price is now $1,534 per person
$1,534
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,006 reviews)
Fabulous experience. Front desk staff was extremely helpful, friendly, and efficient. Especially while checking-in. Would come back again! Rooms are thoughtfully designed and have amazing views!

Reviewed on Jul 5, 2026

Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Save 100% on your flight
Price was $1,072, price is now $619 per person
$619
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.4/10 Good! (3,239 reviews)
Very convenient location and very attentive staff. Thanks for another great stay!

Reviewed on Jul 10, 2026

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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.
See properties

What to do in Southold

great fun with friends

Full Day Private Long Island Wine Tours from New York City

$189
per adult
Full Day Private Long Island Wine Tours from New York City
See all activities in Southold

Southold Hotel Deals

The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
$397 nightly
The price is $450 total per night from Jul 26 to Jul 27
$450 total
Jul 26 - Jul 27
Total with taxes and fees
9.4/10 Exceptional! (292 reviews)
"Had an amazing stay here during the off season with our newborn. The room was clean and grounds were beautifully maintained. Can’t wait to come back here this summer to see the property in full action."

Reviewed on Jul 8, 2026

The Shoals Suites and Slips
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundable
$94 nightly
The price is $108 total per night from Jul 12 to Jul 13
$108 total
Jul 12 - Jul 13
Total with taxes and fees
8/10 Very Good! (1,013 reviews)
"The room was hot, and AC barely worked."

Reviewed on Jul 10, 2026

Pier Blue Inn Old Saybrook - Essex
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$532 nightly
The price is $608 total per night from Jul 14 to Jul 15
$608 total
Jul 14 - Jul 15
Total with taxes and fees
8.4/10 Very Good! (664 reviews)
"The staff was helpful and nice. The exterior of the property was fine and the landscaping pretty. However the room was awful - not particularly clean, a noisy, wall ac plugged in next to the bed, felt like a renovated motel room. Sorry not worth $700/ night."

Reviewed on Jul 8, 2026

Sound View Greenport
See all 4,358 properties in Southold
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 $561 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?

  1. Choose your travel dates: The things you'd like to do in Southold and your favorite season can help you decide when to go.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.