Southold Vacations from $327

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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.
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Manhattan
Price was $709, price is now $327 per person
$327
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.4/10 Good! (5,413 reviews)
Everyday we felt well taken care of and the first priority of each staff member we encountered. I can’t believe how many negative reviews I read that had to be false. Not a single elevator issue, staff member issue, room was great, bed was comfortable, room was attended to each day, and the staff even tucked in my daughter and her friends build a bear each day while attending to the room.

Reviewed on Jan 9, 2026

Topping Rose House

Topping Rose House

4.5 out of 5
Price was $1,133, price is now $522 per person
$522
per person
Feb 13 - Feb 15
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (136 reviews)
Great rooms, staff and food

Reviewed on Sep 28, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was $1,136, price is now $542 per person
$542
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (2,008 reviews)
The hospitality and customer service is top tier. The ambiance is modern, clean, and the city view was incredible of the Empire State Building.Our family loves staying at the various Melia hotels.

Reviewed on Jan 8, 2026

Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Price was $726, price is now $390 per person
$390
per person
Apr 5 - Apr 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (6,546 reviews)
Very clean but older, small room and bed was not comfortable-seemed like a hard box with very little give to it. Staff was friendly, walkable to everything. Bodega was really good next-door

Reviewed on Jan 10, 2026

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was $627, price is now $347 per person
$347
per person
Apr 5 - Apr 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
Very nice property. Clean. Friendly. Great rooms

Reviewed on Jan 4, 2026

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Discover the most popular places to visit in Southold

Cleanest, prettiest winery on the east end of Long Island! Try the Cuvee' Rose!

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

Corey Creek Winery

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

Corey Creek Winery

The Old Field Vineyards

You can enjoy a tasting or tour at The Old Field Vineyards during your travels to Southold. Stroll along the beaches or discover the sunsets in this family-friendly area.

The Old Field Vineyards

What to do in Southold

The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

$179
per adult
76% of travellers recommend
The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC
Long Island Wine Tour North Fork Sights, Bites & Flights Full-Day

Long Island Wine Tour North Fork Sights, Bites & Flights Full-Day

$559
per adult
Long Island Wine Tour North Fork Sights, Bites & Flights Full-Day
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
$157 nightly
The price is $180 total per night from Feb 10 to Feb 11
$180 total
Feb 10 - Feb 11
Total with taxes and fees
9.4/10 Exceptional! (234 reviews)
The room was much larger than expected, very clean. Perfect location, Melissa at the front desk was very helpful

Reviewed on Jan 1, 2026

The Shoals Suites and Slips
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
$223 nightly
The price is $256 total per night from Jan 14 to Jan 15
$256 total
Jan 14 - Jan 15
Total with taxes and fees
8.8/10 Excellent! (1,005 reviews)
Great place!

Reviewed on Dec 31, 2025

Water's Edge Resort & Spa
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
$74 nightly
The price is $85 total per night from Jan 11 to Jan 12
$85 total
Jan 11 - Jan 12
Total with taxes and fees
7.8/10 Good! (1,002 reviews)
Parking was very convenient, and the property is pet-friendly with a nice grassy area in the back for pets to relieve themselves. The room was clean and staff were friendly, although queen size bed felt like twin xl but overall, a pleasant and hassle-free stay.

Reviewed on Dec 31, 2025

Pier Blue Inn Old Saybrook - Essex
See all 4,293 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 $327 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.

Explore a world of travel with Expedia

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