Southport Vacations from $295

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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.
The Thayer Hotel at West Point

The Thayer Hotel at West Point

3.5 out of 5
Price was $379, price is now $295 per person
$295
per person
Mar 20 - Mar 22
found 20 hours ago
Roundtrip flight included
Miami (MIA) to White Plains (HPN)
9/10 Wonderful! (655 reviews)
Excellent service. Attentive staff.

Reviewed on Jan 9, 2026

Hampton Inn & Suites Yonkers

Hampton Inn & Suites Yonkers

2.5 out of 5
Northwest Yonkers
Save 100% on your flight
Price was $485, price is now $347 per person
$347
per person
Apr 5 - Apr 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8.2/10 Very Good! (1,621 reviews)
Front desk staff was polite, friendly and professional Room was clean and very comfortable Would definitely return

Reviewed on Jan 28, 2026

Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
Save 100% on your flight
Price was $543, price is now $417 per person
$417
per person
Apr 22 - Apr 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8/10 Very Good! (1,001 reviews)
It was a perfect short stay there

Reviewed on Jan 23, 2026

Luxury Living in the Heart of NY

Luxury Living in the Heart of NY

4 out of 5
Southeast Yonkers
Save 100% on your flight
Price was $3,080, price is now $2,408 per person
$2,408
per person
Apr 3 - Apr 7
found 1 day ago
Roundtrip flight included
Los Angeles (QLA) to White Plains (HPN)
2/10 (1 review)
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Southport Hotel Deals

Delamar Southport

Delamar Southport

4 out of 5
275 Old Post Rd Southport CT
$246 nightly
The price is $281 total per night from Feb 26 to Feb 27
$281 total
Feb 26 - Feb 27
Total with taxes and fees
9.4/10 Exceptional! (458 reviews)
The room was ready, clean, and there was a bed for our dog and bowls on a tray. The breakfast was excellent, including pastries, eggs, bacon pancakes.fruit and more! The people were friendly and helpful.

Reviewed on Jan 18, 2026

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
$161 nightly
The price is $185 total per night from Mar 1 to Mar 2
$185 total
Mar 1 - Mar 2
Total with taxes and fees
7.4/10 Good! (1,004 reviews)
The position of the desk next to the air-conditioning vent is not ideal. Perhaps a switched position with the bureau/TV is better.

Reviewed on Jan 27, 2026

DoubleTree by Hilton Stamford
Amsterdam Hotel

Amsterdam Hotel

2 out of 5
19 Clarks Hill Ave Stamford CT
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $119 total per night from Feb 14 to Feb 15
$119 total
Feb 14 - Feb 15
Total with taxes and fees
8.4/10 Very Good! (1,737 reviews)
Place was very clean and comfy.

Reviewed on Jan 18, 2026

Amsterdam Hotel
See all 971 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 $295 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.