Southport Vacations from $576

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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.
Sleepy Hollow Hotel

Sleepy Hollow Hotel

3.5 out of 5
Price was $768, price is now $576 per person
$576
per person
Dec 30 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
6.8/10 (1,004 reviews)
This was a great hotel for my family of four. The room was spacious, and clean. We were on the second floor and the employee who checked us in told us where to park so we could use the elevator with our luggage (it isn't close to the front desk). My youngest daughter enjoyed the pool (it was a little chilly, but it was October). We were pleasantly surprised that breakfast was offered for a limited time. It was enough - fruit, bagels, muffins, coffee and juice. We would definitely recommend this hotel to others!

Reviewed on Oct 15, 2025

Luxury NY Home 3BR with Easy Parking

Luxury NY Home 3BR with Easy Parking

3 out of 5
Southeast Yonkers
Save 100% on your flight
Price was $3,910, price is now $2,446 per person
$2,446
per person
Dec 30 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
3/10 (4 reviews)
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 $5,544, price is now $3,507 per person
$3,507
per person
Dec 30 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
2/10 (1 review)
Global Luxury Suites White Plains

Global Luxury Suites White Plains

3.5 out of 5
Save 100% on your flight
Price was $1,126, price is now $801 per person
$801
per person
Dec 30 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
6.8/10 (32 reviews)
Being in an apartment building for an actual stay instead of a house was a first for myself and the family but overall a good stay.

Reviewed on Sep 1, 2025

Luxury NY Home with Free Parking

Luxury NY Home with Free Parking

4 out of 5
Save 100% on your flight
Price was $4,391, price is now $3,443 per person
$3,443
per person
Dec 30 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
No reviews
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Southport Hotel Deals

Delamar Southport

Delamar Southport

4 out of 5
275 Old Post Rd, Southport, CT
$329 nightly
The price is $376 total per night from Nov 9 to Nov 10
$376 total
Nov 9 - Nov 10
Total with taxes and fees
9.4/10 Exceptional! (433 reviews)
"It's in the heart of the city and easy walking distance to many of the historic sites"

Reviewed on Oct 5, 2025

Delamar Southport
Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

4 out of 5
99 East Avenue, Norwalk, CT
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $140 total per night from Oct 26 to Oct 27
$140 total
Oct 26 - Oct 27
Total with taxes and fees
8.6/10 Excellent! (1,359 reviews)
"Beautiful hotel and immaculately clean. The lobby is beautiful and there is a clean, fresh smell everywhere. Our room is adequate in size but very clean. I highly recommend this facility."

Reviewed on Oct 14, 2025

Norwalk Inn & Conference Center
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
$89 nightly
The price is $103 total per night from Oct 26 to Oct 27
$103 total
Oct 26 - Oct 27
Total with taxes and fees
6.4/10 (887 reviews)
"Good parking. Dirty carpet in hallway. Good bed."

Reviewed on Oct 13, 2025

La Quinta Inn & Suites by Wyndham Stamford / New York City
See all 967 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.

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 $576 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.