Title: Southport Vacation Packages & Trips 2026 from CA $1,096 | Expedia.ca [Southport Travel Guide](https://expedia.ca/Southport.dx6134209)[Hotels in Southport](https://expedia.ca/Southport-Hotels.d6134209.Travel-Guide-Hotels)[Vacation Rentals in Southport](https://expedia.ca/Southport-Vacation-Rentals.d6134209.Travel-Guide-VacationRentals)[Flights to Southport](https://expedia.ca/Cheap-Flights-To-Southport.d6134209.Travel-Guide-Flights)[Southport Car Rentals](https://expedia.ca/Car-Rentals-In-Southport.d6134209.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6134209/56369832-5647-4ac2-a0e3-55844ebc2c2b.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Southport Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, 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](https://www.expedia.ca/Fairfield-University-Fairfield.d553248621582621434.Vacation-Attraction), [Sacred Heart University](https://www.expedia.ca/Sacred-Heart-University-New-Haven.d553248635056397660.Vacation-Attraction) and [Total Mortgage Arena](https://www.expedia.ca/Total-Mortgage-Arena-Bridgeport.d6089777.Vacation-Attraction). 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. ![Luxury NYC Home Game Room Free Parking](https://images.trvl-media.com/lodging/124000000/123350000/123346400/123346355/dde34060_edited_b0ec_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Luxury NYC Home Game Room Free Parking CA $1,096 per person May 16 - May 19 found 19 hours ago Roundtrip flight included Toronto (YYZ) to White Plains (HPN) No reviews ![Modern Luxury Home w GameRoom & Parking](https://images.trvl-media.com/lodging/102000000/101330000/101326200/101326114/5bea3ddd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Modern Luxury Home w GameRoom & Parking Southeast Yonkers CA $1,942 per person May 16 - May 19 found 19 hours ago Roundtrip flight included Toronto (YYZ) to White Plains (HPN) 7.2/10 Good! (5 reviews) This was an excellent House My birthday weekend was amazing I totally would book again Reviewed on Mar 17, 2024 ![3BR Prime Luxury NY - Free Parking](https://images.trvl-media.com/lodging/124000000/123770000/123767700/123767642/2653f502_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 3BR Prime Luxury NY - Free Parking CA $1,692 per person May 16 - May 19 found 19 hours ago Roundtrip flight included Toronto (YYZ) to White Plains (HPN) No reviews 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 ![Prime Luxe 3-BR NYC - Free Parking](https://images.trvl-media.com/lodging/124000000/123780000/123777600/123777568/w1213h683x1y0-56baa241_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Prime Luxe 3-BR NYC - Free Parking CA $1,624 per person May 16 - May 19 found 19 hours ago Roundtrip flight included Toronto (YYZ) to White Plains (HPN) No reviews ![Luxury 5 BR Home Free Parking](https://images.trvl-media.com/lodging/123000000/122700000/122696900/122696857/w1199h799x1y1-334231fd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Luxury 5 BR Home Free Parking Bryn Mawr CA $1,218 per person May 16 - May 19 found 19 hours ago Roundtrip flight included Toronto (YYZ) to White Plains (HPN) 2/10 (1 review) ## Ready to book your vacation to Southport? Choose your dates ## Southport Hotel Deals ![Delamar Southport](https://images.trvl-media.com/lodging/4000000/3710000/3703800/3703782/1291b9a0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Delamar Southport 275 Old Post Rd Southport CT CA $254 CA $313 total Apr 12 - Apr 13 includes taxes & 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 [](https://expedia.ca/Hotel-Search?startDate=12%2F04%2F2026&endDate=13%2F04%2F2026&selected=3703782&PinnedHotelID=3703782&HadPinnedHotel=true®ionId=6134209) ![Motel 6 Milford, CT](https://images.trvl-media.com/lodging/1000000/10000/300/291/1144278e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Motel 6 Milford, CT 111 Schoolhouse Road Milford CT Fully refundableReserve now, pay when you stay CA $86 CA $99 total Apr 23 - Apr 24 includes taxes & fees 6.2/10 (1,003 reviews) Everything went as smooth as possible with my stay. My reservation was ready for me when I walked in the door. Parking was well lit and plenty of it complementary coffee in the morning. Reviewed on Apr 2, 2026 [](https://expedia.ca/Hotel-Search?startDate=23%2F04%2F2026&endDate=24%2F04%2F2026&selected=291&PinnedHotelID=291&HadPinnedHotel=true®ionId=6134209) ![Hyatt Place Milford / New Haven](https://images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/80833193_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Place Milford / New Haven 190 Old Gate Lane Milford CT Fully refundableReserve now, pay when you stay CA $177 CA $203 total Apr 27 - Apr 28 includes taxes & fees 8.6/10 Excellent! (1,289 reviews) Room was very spacious and we never felt cramped. Reviewed on Apr 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=27%2F04%2F2026&endDate=28%2F04%2F2026&selected=1562702&PinnedHotelID=1562702&HadPinnedHotel=true®ionId=6134209) [See all 983 properties in Southport](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=05%2F04%2F2026&endDate=06%2F04%2F2026®ionId=6134209) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## 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. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app