Southport Vacation Packages

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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.
Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel

4 out of 5
Price was CA $1,104, price is now CA $909 per person
CA $909
per person
Dec 21 - Dec 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
8.6/10 Excellent! (1,317 reviews)
The big issue with this hotel is that it operates more as a dog kennel than it does a hotel for humans. While the property is nice and the rooms are well kept, it doesn't really matter at the end of the day if you're waking up constantly to barking dogs next door to you and above you when you're trying to sleep. Wasn't restful. And who knows how they remove fleas or ticks or other unwanted leftovers from the animals from the rooms?

Reviewed on Nov 1, 2026

Westchester Marriott

Westchester Marriott

4.5 out of 5
Price was CA $1,399, price is now CA $1,115 per person
CA $1,115
per person
Jan 2 - Jan 7
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YTO) to White Plains (HPN)
9/10 Wonderful! (675 reviews)

Hyatus Luxury Residences Stamford

Hyatus Luxury Residences Stamford

4.5 out of 5
Downtown Stamford
Price was CA $2,315, price is now CA $1,990 per person
CA $1,990
per person
Dec 26 - Dec 31
found 21 hours ago
Roundtrip flight included
Montreal (YUL) to White Plains (HPN)
9.6/10 Exceptional! (28 reviews)
Exceptional communication. Great common area amenities. Room was good, beds were comfortable. Close to Target, Dunkin etc. First time check-in and parking needs to be simplified. E.g. picking up fobs from the front desk during check-in would make the experience even better. Overall excellent!

Reviewed on Oct 24, 2026

3BR Prime Luxury NY - Free Parking

3BR Prime Luxury NY - Free Parking

2 out of 5
Price was CA $2,837, price is now CA $2,472 per person
CA $2,472
per person
Dec 6 - Dec 9
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to White Plains (HPN)
6/10 (1 review)
Check-in was confusing and poorly organized, which made the start of the stay frustrating. The room itself was fine and comfortable, but the photos on the website were misleading and didn’t match what we saw in person. Overall, an okay room but not the experience we expected.

Reviewed on Mar 30, 2026

Delamar Greenwich Harbor

Delamar Greenwich Harbor

4 out of 5
Price was CA $1,527, price is now CA $1,332 per person
CA $1,332
per person
Dec 21 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTZ) to White Plains (HPN)
9.4/10 Exceptional! (1,002 reviews)
our room was just okay not worth the money. The walls are paper thin could hear our neighbors full conversation at 6am. When we mentioned it to the front desk they could have cared less.

Reviewed on Nov 1, 2026

Ready to book your vacation to Southport?

 

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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 $382 per night from Nov 15 to Nov 16
CA $382
CA $495 total
Nov 15 - Nov 16
includes taxes & fees
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 $298 per night from Nov 8 to Nov 9
CA $298
CA $342 total
Nov 8 - Nov 9
includes taxes & fees
Hyatt Regency Greenwich
J House Greenwich

J House Greenwich

4 out of 5
1114 E. Putnam Ave Riverside CT
The price is CA $389 per night from Nov 20 to Nov 21
CA $389
CA $505 total
Nov 20 - Nov 21
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Steakhouse was very disappointing but stay was very pleasant!"

Reviewed on Oct 31, 2026

J House Greenwich
See all 996 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

Stay near popular Southport attractions

Southport Beach

9.6/10 (5 reviews)
Why not spend a lazy afternoon at Southport Beach during your trip to Southport? You can enjoy the restaurants while in the area.
See properties

Frequently asked questions

How much does a Southport vacation package cost?
Offering excellent value package deals from CA $909 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.

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