Southold Vacations from $222

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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.
Windrose On Hudson

Windrose On Hudson

3 out of 5
Price was $463, price is now $222 per person
$222
per person
Jan 26 - Jan 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
15.6/10 Exceptional! (80 reviews)
I wish there was a coffee maker in the room, also the TV was very small and angled away from the bed. It was super quiet, which was great, and very clean and warm.

Reviewed on Nov 16, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $560, price is now $270 per person
$270
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
18.4/10 Exceptional! (2,008 reviews)
Staff and amenities were fabulous!! Stayed here for 5 nights on a trip for tourism and it was perfectly situated for the Broadway shows and to get away from the hustle and bustle of being a tourist.

Reviewed on Nov 24, 2025

Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was $661, price is now $322 per person
$322
per person
Feb 12 - Feb 15
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
17.2/10 Exceptional! (2,613 reviews)
The location was ideal for our stay. The restaurant food was amazing.

Reviewed on Nov 22, 2025

Hilton Garden Inn Westchester Dobbs Ferry, NY

Hilton Garden Inn Westchester Dobbs Ferry, NY

3 out of 5
Price was $458, price is now $229 per person
$229
per person
Jan 30 - Feb 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
16.8/10 Exceptional! (1,001 reviews)
Beautiful place to be

Reviewed on Nov 20, 2025

The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Manhattan
Price was $694, price is now $358 per person
$358
per person
Feb 15 - Feb 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
18/10 Exceptional! (1,825 reviews)
I had a great experience there and a very comfortable stay

Reviewed on Nov 25, 2025

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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

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

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

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
$174 nightly
The price is $199 total per night from Dec 26 to Dec 27
$199 total
Dec 26 - Dec 27
Total with taxes and fees
9.4/10 Exceptional! (221 reviews)
This was a stunning place to stay in all respects. The large room was wonderrful. Thank you!

Reviewed on Nov 8, 2025

The Shoals Suites and Slips
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
$101 nightly
The price is $116 total per night from Dec 2 to Dec 3
$116 total
Dec 2 - Dec 3
Total with taxes and fees
7.6/10 Good! (1,007 reviews)
Staff was kind. Easy, comfortable stay.

Reviewed on Nov 19, 2025

Quality Inn Old Saybrook - Westbrook
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$203 nightly
The price is $232 total per night from Nov 30 to Dec 1
$232 total
Nov 30 - Dec 1
Total with taxes and fees
8.4/10 Very Good! (593 reviews)
Amazing views and comfy bed and room. No sound privacy between the rooms at all! I guess they o relooked sound insulation in an otherwise gorgeous renovation of a roadside motel.

Reviewed on Nov 19, 2025

Sound View Greenport
See all 4,306 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 $222 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.