Southold Vacations from CNY4,148

Book a Hotel + Flight or Car together to unlock savings

    Plan, book, travel with confidence
    payments icon
    Better together
    You can save when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Your Southold Vacation

There's no better way to get away than with one of our vacation packages to Southold. The rich history and coastal scenery are just two of the many reasons you'll want to stay in this awesome city. If taking in sights is on the agenda during your trip to Southold, look around well-known attractions like 67 Steps Beach, Kontokosta Winery and Sunset Beach. No matter your travel plans or the size of your budget, putting together a tailored Southold vacation is a walk in the park with Expedia.

The Latest Southold Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Westin New York Grand Central

The Westin New York Grand Central

4.5 out of 5
Manhattan
per person
Jul 12 - Jul 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (2,423 reviews)
Loved the location. Staff was very friendly. The bathrooms could use a little refresh and the air conditioning could use some work. Overall the room was clean and the beds were fantastic!!

Reviewed on 1 Jun 2024

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
per person
Aug 10 - Aug 13
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (545 reviews)
the incredible location I had a wonderful experience, want to come back

Reviewed on 28 May 2024

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
Jul 12 - Jul 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (3,691 reviews)
Great breakfast. Nice amenities but room small and lighting harsh.

Reviewed on 31 May 2024

RIU Plaza Manhattan Times Square

RIU Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
Jul 12 - Jul 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (3,099 reviews)
A great location, rooms were spacious and clean. Stuff were very helpful. Nice hotel.

Reviewed on 28 May 2024

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Jul 12 - Jul 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,004 reviews)
Great location! Great service!

Reviewed on 20 May 2024

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

Southold Hotel Deals

The Shoals Suites and Slips
The Shoals Suites and Slips
3.5 out of 5
61600 Main Rd, Southold, NY
The price is CNY3,367 per night from Jun 2 to Jun 3
CNY3,367
CNY4,024 total
includes taxes & fees
2 Jun - 3 Jun
9.4/10 Exceptional! (80 reviews)
"Amazing time"

Reviewed on 28 May 2024

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 refundableReserve now, pay when you stay
The price is CNY572 per night from Jun 2 to Jun 3
CNY572
CNY658 total
includes taxes & fees
2 Jun - 3 Jun
7.6/10 Good! (785 reviews)
"Just what you need for a quick stay. Really great breakfast option across the street. Hard to get anything late."

Reviewed on 27 May 2024

Pier Blue Inn Old Saybrook - Essex
Quality Inn Old Saybrook - Westbrook
Quality Inn Old Saybrook - Westbrook
2.5 out of 5
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is CNY710 per night from Jun 3 to Jun 4
CNY710
CNY817 total
includes taxes & fees
3 Jun - 4 Jun
7.4/10 Good! (964 reviews)
"Great hotel for the money, though it's a little off the beaten path (I had no idea where to find Old Saybrook from the hotel location). Still, it was perfect for my needs. They had a nice (free) continental breakfast and the pool area was great."

Reviewed on 28 May 2024

Quality Inn Old Saybrook - Westbrook
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Southold vacation package cost?
From just CNY4,148. Yes, you read that correctly. Our Southold packages are a simple way to make your budget go further. Combine your preferred flights, hotels and rental car and explore this popular destination.
How do I get a cheap travel package to Southold?
Search for flights that suit your busy schedule, add a hotel room to your booking and see how much you save with a Southold vacation package. It’s as easy as that! From flights and hotels to tours and rental cars, Expedia makes traveling cheap and easy. And with more than 550 air carriers and 1,000,000 properties worldwide to pick from, you’ll never be short of choice.
How far in advance should I book my Southold vacation?
Smart travelers will likely want to reserve their seats as early as possible. You can usually start comparing international airfares on Expedia up to 12 months before your flight. If you’re late to book, don’t stress. Cheap prices occasionally occur just weeks prior to departure.
What does an Expedia Southold travel package include?
Hotels, flights and car rentals — we bring you the very best deals. All you have to do is figure out your ideal combination. After you’ve made your booking, you can add on the fun stuff like sightseeing activities. Our travel packages make it easy to put together an awesome Southold escape.
What should I know before booking a Southold travel package?
So many places to wander around, so many things to see and do. With a package, you’ll be able to afford more of them. Bundle your hotels, flights and rental cars and see how much you save.
Can I choose my airline with a Southold Expedia vacation package?
Yes — and it’s easy too. Expedia has access to more than 550 partner airlines throughout the world. Our packages give you the freedom to take your pick of available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Southold vacation package?
If your travel plans in Southold have changed, it’s good to know that it is possible to cancel your booking. If you booked in the last 24 hours, you may be able to get a refund. If your booking is older than that, your hotel, airline or car rental company may charge a fee. To learn more, check our Customer Service Portal.

Discover the most popular places to visit in Southold

Image for Sparkling Pointe

Sparkling Pointe

You can enjoy a tasting or tour at Sparkling Pointe during your travels to Southold. Discover the sunsets and wineries in this family-friendly area.

Sparkling Pointe
Image for Croteaux Vineyards

Croteaux Vineyards

You can enjoy a tasting or tour at Croteaux Vineyards during your travels to Southold. Wander the beautiful beaches in this family-friendly area.

Croteaux Vineyards
Image for Sannino's Bella Vita Vineyard

Sannino's Bella Vita Vineyard

You can enjoy a tasting or tour at Sannino's Bella Vita Vineyard during your travels to Southold. Wander the beaches or discover the sunsets in this family-friendly area.

Sannino's Bella Vita Vineyard

What to do in Southold

Image for Long Island Full Day Wine and Food Tasting Vineyard Tour from NYC

Long Island Full Day Wine and Food Tasting Vineyard Tour from NYC

CNY154
Per adult
Long Island Full Day Wine and Food Tasting Vineyard Tour from NYC
Image for Private Hamptons Tour with Outlet Center Shopping

Private Hamptons Tour with Outlet Center Shopping

CNY1,199
Per adult
Private Hamptons Tour with Outlet Center Shopping
See all activities in Southold

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.