Southport Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Top Southport Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Modern Comfort in the Heart of NYC
Southeast Yonkers
CA $1,037
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
3.6/10 (4 reviews)
It took calling the booking website customer service to get in contact with the host. I end up getting a different property that the one I reserved but the new on was more bedrooms, at the end I work out but it took some long coy with the host.
Reviewed on Jun 29, 2026
Luxury NY Home with Free Parking
CA $5,292
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to White Plains (HPN)
8/10 Very good! (1 review)
Rooms were very clean, well decorated however bathrooms were not. Parking was accessible and perfect. Some appliances did not work like iron stained my clothes and coffee machine did not work. Everything else was fine.
Reviewed on Nov 8, 2025
Luxury 3BR Family Home Game Room Parking
Bryn Mawr
CA $1,264
per person
Oct 28 - Nov 2
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
6.8/10 (3 reviews)
This is a scam. Arrived at the supposed address only to be met by the owner of the property nextdoor informing me that address did not exist and unfortunately we weren’t the only ones that experienced this. Was a a terrible start to a family vacation, luckily a Hampton inn was right down the road and had vacancies so were able to book same day.
Reviewed on Aug 29, 2026
Ready to book your vacation to Southport?
Southport Hotel Deals
Delamar Southport
275 Old Post Rd Southport CT
CA $336
CA $441 total
Sep 20 - Sep 21
includes taxes & fees
Hyatt Regency Greenwich
1800 E Putnam Avenue Old Greenwich CT
Fully refundableReserve now, pay when you stay
CA $247
CA $284 total
Sep 27 - Sep 28
includes taxes & fees
8.8/10 Excellent! (1,138 reviews)
"Safe easy clean"
Reviewed on Sep 4, 2026
Trumbull Marriott Shelton
180 Hawley Ln Trumbull CT
Fully refundableReserve now, pay when you stay
CA $206
CA $236 total
Sep 7 - Sep 8
includes taxes & fees
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.
Frequently asked questions
How much does a Southport vacation package cost?
Offering excellent value package deals from CA $1,037 on Expedia, you'll be surprised at how little a vacation to Southport costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Southport?
June, September and October are great times to look for cheap Southport vacation packages. Opting to travel in less busy periods means you can usually find reduced prices on accommodations and flights.
How many days is enough for Southport?
To get the most out of your Southport vacation, we suggest booking for 2 days. Divide your time between visiting Total Mortgage Arena, Jennings Beach and other leading sights, in addition to experiencing neighbourhoods like Brooklawn - St. Vincent and Black Rock Historic District. If you've got some time to spare, add a day trip to your Southport vacation itinerary.
How to find the best Southport package deals?
Start your search for a Southport package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select some filters, like "Popular locations" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Southport package deal straight away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Southport adventure off to a flying start.
Is it cheaper to book a Southport vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Southport vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Southport?
If you're planning an impromptu Southport adventure, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land amazing deals on your flights and hotels by booking well in advance.
How to plan a trip to Southport?
- Choose the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Southport.
- Work out your budget: Make sure you have enough money to pay for everything from meals and transportation to flights and activities. Your accommodations will probably be the largest expense during your trip to Southport.
- Decide how long to go for: Now that you're up to speed on Southport, you can work out the right length of your vacation. Create a draft plan and give yourself enough time to cover everything you want to do.
- Bundle your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to choose a Southport vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
