Southport Vacations from $711

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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.
Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking

2 out of 5
Bryn Mawr
Save 100% on your flight
Price was $1,062, price is now $711 per person
$711
per person
May 20 - May 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
9/10 Wonderful! (2 reviews)
Beautiful layout. Property had everything that was needed for an awesome stay.

Reviewed on Feb 27, 2026

Luxury 5 BR Home Free Parking

Luxury 5 BR Home Free Parking

2 out of 5
Bryn Mawr
Save 100% on your flight
Price was $1,187, price is now $731 per person
$731
per person
May 15 - May 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
2/10 (1 review)
Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
Save 100% on your flight
Price was $1,190, price is now $739 per person
$739
per person
Jun 30 - Jul 7
found 4 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to White Plains (HPN)
8.2/10 Very Good! (1,043 reviews)
The staff at breakfast would serve the coffee once and rarely came to fill up the cups unless we asked. I feel that there is staff shortage.

Reviewed on Apr 5, 2026

Luxury 3 BR Near NYC with Easy Parking

Luxury 3 BR Near NYC with Easy Parking

2 out of 5
Bryn Mawr
Save 100% on your flight
Price was $4,644, price is now $2,955 per person
$2,955
per person
Jun 25 - Jun 30
found 10 hours ago
Roundtrip flight included
Dallas (DFW) to White Plains (HPN)
No reviews
Family Cottage with 4 King Beds

Family Cottage with 4 King Beds

2 out of 5
Historic District
Save 100% on your flight
Price was $2,328, price is now $1,559 per person
$1,559
per person
May 15 - May 18
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
$208 nightly
The price is $237 total per night from Apr 12 to Apr 13
$237 total
Apr 12 - Apr 13
Total with taxes and fees
9.6/10 Exceptional! (468 reviews)
Excellent staff and restaurant, cozy and welcome spa with super friendly staff. Only thing is that it’s close to the highway and noise level is noticeable.

Reviewed on Mar 26, 2026

Delamar Southport
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 23 to Apr 24
$75 total
Apr 23 - Apr 24
Total with taxes and fees
6.2/10 (1,002 reviews)
Didn't use the laundry and took an Uber.

Reviewed on Apr 9, 2026

Motel 6 Milford, CT
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
$106 nightly
The price is $122 total per night from Apr 19 to Apr 20
$122 total
Apr 19 - Apr 20
Total with taxes and fees
8.6/10 Excellent! (1,291 reviews)
The breakfast is excellent. A lot of choices. The room is spacious and clean. The staff are nice.

Reviewed on Apr 6, 2026

Hyatt Place Milford / New Haven
See all 988 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 $711 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.