Southport Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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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.

Top Southport Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

2.5 out of 5
Price was CA $716, price is now CA $601 per person
CA $601
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to White Plains (HPN)
8.4/10 Very good! (1,730 reviews)
Staff were helpful. Breakfast could have been better. Maybe some fruit salad

Reviewed on Jul 14, 2026

Delamar Southport

Delamar Southport

4 out of 5
Price was CA $2,090, price is now CA $1,610 per person
CA $1,610
per person
Sep 9 - Sep 14
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
9.6/10 Exceptional! (487 reviews)
Wow, hidden gem. Place is amazing, rooms are well appointed and stylish. Restaurant is phenomenal and the staff from your car pulling up to checkout is superior.

Reviewed on Jul 13, 2026

Stamford Suites

Stamford Suites

4 out of 5
Downtown Stamford
Price was CA $1,681, price is now CA $1,353 per person
CA $1,353
per person
Aug 22 - Aug 29
found 1 hour ago
Roundtrip non-stop flight included
Ottawa (YOW) to White Plains (HPN)
6.4/10 (134 reviews)
Got there got my key I went to check the room out and the bed was dirty sheets needed to be changed

Reviewed on Jul 12, 2026

Luxury NY Home 3BR with Easy Parking

Luxury NY Home 3BR with Easy Parking

3 out of 5
Southeast Yonkers
Price was CA $3,995, price is now CA $3,293 per person
CA $3,293
per person
Sep 3 - Sep 7
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to White Plains (HPN)
3/10 (4 reviews)

Delamar Greenwich Harbor

Delamar Greenwich Harbor

4 out of 5
Price was CA $2,701, price is now CA $2,284 per person
CA $2,284
per person
Sep 3 - Sep 7
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to White Plains (HPN)
9.4/10 Exceptional! (992 reviews)
Nice hotel but front desk and concierge could improve their services. Very little information about the hotel or area offered.

Reviewed on Jul 11, 2026

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Southport Hotel Deals

Delamar Southport

Delamar Southport

4 out of 5
275 Old Post Rd Southport CT
The price is CA $345 per night from Aug 3 to Aug 4
CA $345
CA $418 total
Aug 3 - Aug 4
includes taxes & fees
9.6/10 Exceptional! (493 reviews)
"Wow, hidden gem. Place is amazing, rooms are well appointed and stylish. Restaurant is phenomenal and the staff from your car pulling up to checkout is superior."

Reviewed on Jul 13, 2026

Delamar Southport
Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
1800 E Putnam Avenue Old Greenwich CT
Fully refundableReserve now, pay when you stay
The price is CA $296 per night from Jul 26 to Jul 27
CA $296
CA $340 total
Jul 26 - Jul 27
includes taxes & fees
8.6/10 Excellent! (1,085 reviews)
"good food good service enjoyed our stay"

Reviewed on Jul 13, 2026

Hyatt Regency Greenwich
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
The price is CA $143 per night from Aug 11 to Aug 12
CA $143
CA $165 total
Aug 11 - Aug 12
includes taxes & fees
6.6/10 (1,544 reviews)
"It was ok"

Reviewed on Jul 14, 2026

La Quinta Inn & Suites by Wyndham Stamford / New York City
See all 978 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Southport vacation package cost?
Offering excellent value package deals from CA $601 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.