Southport Vacations from $318
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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
- Red Carpet Inn
Feb 4 - Feb 8Red Carpet Inn + Flight
Cove - East Side - Shippan4 nights2.0 star property7.0/10 - Good (1,071 reviews)Roundtrip • Houston (HOU) - White Plains (HPN)IAH - JFK • Nonstop LGA - IAH • 1 stop$379$318found 1 day agoper traveler - Stamford Marriott
Dec 30 - Jan 4Stamford Marriott + Flight
Downtown Stamford5 nights3.5 star property8.0/10 - Very good (1,000 reviews)Roundtrip • Dallas (DFW) - White Plains (HPN)DFW - LGA • Nonstop LGA - DFW • 1 stop$992$818found 1 day agoper traveler - Hilton Garden Inn Norwalk
Dec 28 - Jan 3Hilton Garden Inn Norwalk + Flight
Cranbury6 nights3.0 star property8.2/10 - Very good (1,007 reviews)"I bought the breakfast and it was not good. I think for the price, it should have been better, including better offerings. They show a picture of breakfast in the elevator but don't actually offer that during breakfast time."Reviewed November 11, 2026Roundtrip • Atlanta (ATL) - White Plains (HPN)ATL - EWR • Nonstop EWR - ATL • Nonstop$1,104$925found 1 day agoper traveler - West Gate Inn Nyack
Feb 4 - Feb 8West Gate Inn Nyack + Flight
Nyack4 nights3.0 star property7.4/10 - Good (1,521 reviews)Roundtrip • Houston (HOU) - White Plains (HPN)IAH - JFK • Nonstop LGA - IAH • 1 stop$445$379found 1 day agoper traveler - Home & Away Hotel-Style
Jan 15 - Jan 17Home & Away Hotel-Style + Flight
West Norwalk2 nights2.0 star property8.0/10 - Very good (3 reviews)"Apt in cellar of old house, steep steps, renovation not complete especially HVAC"Reviewed November 2, 2026Roundtrip • Dallas (DFW) - White Plains (HPN)DFW - HPN • 1 stop HPN - DFW • 1 stop$765$653found 6 hours agoper traveler
Where to stay near Southport
Stamford
Travelers seeking a dynamic getaway will find Stamford to be the perfect base to explore a blend of urban excitement and outdoor charm. With attractions like the vibrant shopping along Greenwich Avenue, the artistic allure of The Glass House, and the historical richness of Historic South Norwalk, Stamford offers diverse experiences year-round. Located about 17 miles by car from Southport, it's easily accessible for those looking to enjoy both city life and nature. Stamford is a smart choice for your next hotel stay.
Fairfield
Experience the charm of Fairfield, an excellent hub for travelers seeking a blend of culture, outdoor activities, and family-friendly fun. With attractions like Fairfield University and Jennings Beach, along with the exciting Total Mortgage Arena, there's something for everyone to enjoy. Located about 1 mile by car from Southport, Fairfield offers easy access to vibrant local experiences and a relaxed atmosphere. Choosing Fairfield for your stay ensures a delightful getaway filled with diverse activities and convenient accommodations.
Norwalk
If you are a family traveler, look no further than Norwalk, which features a mix of outdoor adventures and urban experiences. Explore the captivating Historic South Norwalk, enjoy the sandy shores of Compo Beach, or visit the modern Fairfield University. With a variety of shopping and dining options, Norwalk has something for everyone. It’s about an 8-mile drive from Southport, making it a smart choice for your stay while you explore this vibrant city.
Bridgeport
Immerse yourself in Bridgeport, where family travelers can easily access a rich blend of outdoor adventures and city experiences. With attractions like Fairfield University, the Total Mortgage Arena, and the charming Bridgeport Downtown South Historic District, there’s something for everyone to enjoy. Located about 6 miles away from Southport, Bridgeport offers a convenient base for exploring the local beaches and sports facilities. Choosing Bridgeport for your stay ensures you'll have a vibrant and engaging getaway.
Westport
Travelers seeking a delightful getaway will find Westport to be the perfect base, offering a blend of outdoor activities, scenic beauty, and cultural experiences. With attractions like the picturesque Compo Beach, the educational charm of Fairfield University, and the historic allure of South Norwalk, Westport caters to families, couples, and leisure seekers alike. Located about 4 miles by car from Southport, this city ensures easy access to both relaxation and adventure, making it a smart choice for your vacation stay.
Southport Hotel Deals
"While we normally love Delamar properties, Westport is not up to the standards of the other Delamars. This was our second stay in Westport and it was particularly disappointing. It was very evident that, despite it being a new hotel, soundproofing is non-existent here. From the time we arrived in our room, there were running footsteps above us that were so loud it actually rattled the mirror in the bathroom. And this went on until the middle of the night. We found out the next day that there was...
"The hotel is nice and clean; the room size reminded me of a European room (smaller, with a tight bathroom). The property is near a busy bar called the Seagrape, which college kids frequent during the academic season. No front desk or staff to ask about a room change, a sink clog, or a late checkout; call the number and leave a voicemail. However, they addressed 2/3 concerns, but there was no communication."
Norwalk Inn & Conference Center
Norwalk Inn & Conference Center"Everything was great"
Best Western Plus Fairfield Hotel
Best Western Plus Fairfield Hotel
"Being by the water"
Frequently Asked Questions
How much does a Southport vacation package cost?
Offering excellent value package deals from $318 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.