Southport Vacations from $271

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Your Southport Vacation

The coastal scenery and lively atmosphere are just the beginning of the things Southport has going for it. Discover the sights and sounds of this fascinating city your way with a personalized Southport vacation package. You'll want to take in some sights during your trip to Southport. Make time for famous attractions like Fairfield University, Sacred Heart University and Total Mortgage Arena. Check out Expedia's extensive range of travel options and begin planning your ideal vacation to Southport today.

The Latest Southport vacation packages

Price found within the past 48 hours. Click for updated prices.
Residence Inn by Marriott Yonkers Westchester County

Residence Inn by Marriott Yonkers Westchester County

3 out of 5
Northwest Yonkers
Save 100% on your flight
Price was $368, price is now $271 per person
$271
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8.6/10 Excellent! (934 reviews)
I stayed there after a major surgery. It was just perfect and I recovered well. The room service was accessible whenever I needed. It was a peaceful atmosphere. The elevators were always working. I stayed for two weeks and never ran into any issue. I will definitely return and will recommend it to my friends and family.

Reviewed on Oct 23, 2025

Hotel NoMa, Trademark Collection by Wyndham

Hotel NoMa, Trademark Collection by Wyndham

3 out of 5
Save 100% on your flight
Price was $873, price is now $522 per person
$522
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8/10 Very Good! (1,002 reviews)
Nice clean hotel in lower westchester

Reviewed on Oct 19, 2025

Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
Save 100% on your flight
Price was $539, price is now $387 per person
$387
per person
Dec 26 - Dec 30
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8/10 Very Good! (1,021 reviews)
Fantastic property and location. Incredible history and staff was helpful.

Reviewed on Oct 23, 2025

Courtyard by Marriott Yonkers Westchester County

Courtyard by Marriott Yonkers Westchester County

3 out of 5
Northwest Yonkers
Price was $947, price is now $694 per person
$694
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8.8/10 Excellent! (1,241 reviews)
I had a very nice stay. My only feedback is that I wish the coffee station were open in the morning.

Reviewed on Oct 13, 2025

Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
Price was $527, price is now $389 per person
$389
per person
Jan 1 - Jan 4
found 1 day ago
Roundtrip flight included
Miami (MIA) to White Plains (HPN)
8/10 Very Good! (1,221 reviews)
Breakfast was great!

Reviewed on Oct 22, 2025

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Southport Hotel Deals

Delamar Southport

Delamar Southport

4 out of 5
275 Old Post Rd, Southport, CT
$318 nightly
The price is $364 total per night from Oct 26 to Oct 27
$364 total
Oct 26 - Oct 27
Total with taxes and fees
9.4/10 Exceptional! (434 reviews)
Good

Reviewed on Oct 18, 2025

Delamar Southport
DoubleTree by Hilton Stamford

DoubleTree by Hilton Stamford

3.5 out of 5
1 First Stamford Pl, Stamford, CT
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $159 total per night from Nov 23 to Nov 24
$159 total
Nov 23 - Nov 24
Total with taxes and fees
7.2/10 Good! (1,004 reviews)
Very accommodating, clean and modern

Reviewed on Oct 24, 2025

DoubleTree by Hilton Stamford
La Quinta Inn & Suites by Wyndham Stamford / New York City

La Quinta Inn & Suites by Wyndham Stamford / New York City

3 out of 5
135 Harvard Avenue, Stamford, CT
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $97 total per night from Nov 23 to Nov 24
$97 total
Nov 23 - Nov 24
Total with taxes and fees
6.4/10 (896 reviews)
Stayed with my brother for one night on our way back home from a trip up North for the weekend. Easy check in/out, a very pleasant staff, great rates, and the room was clean and comfortable. If we found ourselves in this area again, we’d absolutely book here.

Reviewed on Oct 20, 2025

La Quinta Inn & Suites by Wyndham Stamford / New York City
See all 972 properties in Southport
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 Southport Vacation Packages

Southport Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Westchester County Airport (HPN)
Population
1,600
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Jennings Beach, Norwalk Maritime Aquarium and Compo Beach

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Frequently asked questions

How much does a Southport vacation package cost?
Offering excellent value package deals from $271 on Expedia, you'll be pleasantly surprised at how much a vacation to Southport costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Southport?
If you're hoping to book a cheap Southport vacation package, consider visiting in June, July and September. You're likely to find better prices on hotels and flights during these quieter months — perfect for a budget-friendly break.
How many days is enough for Southport?
The ideal duration for your Southport vacation depends on what you'd like to see. Generally, a few days to a week will give you enough time to visit all the leading attractions and discover some hidden gems along the way.
How to find the best Southport package deals?
Finding a cheap Southport package deal is a breeze with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget range, add a couple of filters and browse what's available. You can customize your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Southport package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Southport vacation as a package?
You can enjoy significant savings on your Southport getaway by booking a tailored vacation package. Click on the "Package" heading, then select your destination and travel dates to view the best hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Southport?
If you're planning a spur-of-the-moment Southport getaway, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can score sensational deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Southport vacation packages?
Your Southport getaway should be a relaxing escape from your busy life, not a reason for money worries. So to allow you extra flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the 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.