Southport Vacations from $427

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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.
Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
Price was $564, price is now $427 per person
$427
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to White Plains (HPN)
8/10 Very Good! (1,379 reviews)
Great location for access to the White Plains. Breakfast items are limited, as most places these days. Receptionist was friendly but slow

Reviewed on Mar 16, 2026

Cromwell Manor Inn

Cromwell Manor Inn

4 out of 5
Price was $2,008, price is now $1,435 per person
$1,435
per person
Jun 7 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to White Plains (HPN)
9.4/10 Exceptional! (95 reviews)
An interesting and beautiful historical site. The mansion has been beautifully preserved and simultaneously updated with all the modern amenities needed to be comfortable, including well-equipped bathrooms and comfortable beds. The owners love to make breakfast for the guests so don’t skip that part of the experience. Cornwall itself is a hidden gem and wonderful escape. Enjoy!

Reviewed on Jan 18, 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 $3,234, price is now $2,322 per person
$2,322
per person
May 27 - May 31
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to White Plains (HPN)
2/10 (1 review)
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 $2,544, price is now $1,837 per person
$1,837
per person
May 27 - May 31
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to White Plains (HPN)
3/10 (4 reviews)
Stamford Marriott Hotel & Spa

Stamford Marriott Hotel & Spa

3.5 out of 5
Downtown Stamford
Save 100% on your flight
Price was $1,126, price is now $855 per person
$855
per person
May 27 - Jun 2
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to White Plains (HPN)
8/10 Very Good! (1,002 reviews)
Th room was fine, staff was great. Really enjoyed the spa there.

Reviewed on Feb 27, 2026

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Southport Hotel Deals

Delamar Southport

Delamar Southport

4 out of 5
275 Old Post Rd Southport CT
$224 nightly
The price is $255 total per night from Mar 22 to Mar 23
$255 total
Mar 22 - Mar 23
Total with taxes and fees
9.6/10 Exceptional! (465 reviews)
Clean room, friendly staff, lovely complimentary breakfast! Gym was also clean. Would highly recommend it.

Reviewed on Mar 16, 2026

Delamar Southport
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
190 Old Gate Lane Milford CT
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $116 total per night from Apr 5 to Apr 6
$116 total
Apr 5 - Apr 6
Total with taxes and fees
8.6/10 Excellent! (1,273 reviews)
Staff were welcoming, helpful, and efficient. Rooms are comfortable and layout is well-designed. Very reasonable pricing.

Reviewed on Mar 17, 2026

Hyatt Place Milford / New Haven
Motel 6 Milford, CT

Motel 6 Milford, CT

2 out of 5
111 Schoolhouse Road Milford CT
Fully refundableReserve now, pay when you stay
$65 nightly
The price is $75 total per night from Apr 5 to Apr 6
$75 total
Apr 5 - Apr 6
Total with taxes and fees
6.2/10 (1,001 reviews)
For a non-smoking motel…it smelled so bad. The smell of weed and cigarettes was horrible. Our room wasn’t ready at 3:00 check in. Only 1 towel in the bathroom. No facecloth, no hand towel. 1 bath towel! No tissues, 3 sheets of toilet paper left on roll! Seriously, they couldn’t put on a fresh roll ...

Reviewed on Mar 16, 2026

Motel 6 Milford, CT
See all 976 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 $427 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.