Title: Southold Vacation Packages & Trips 2026 from CA $1,367 | Expedia.ca [Hotels in Southold](https://expedia.ca/Southold-Hotels.d183719.Travel-Guide-Hotels)[Vacation Rentals in Southold](https://expedia.ca/Southold-Vacation-Rentals.d183719.Travel-Guide-VacationRentals)[Flights to Southold](https://expedia.ca/Cheap-Flights-To-Southold.d183719.Travel-Guide-Flights)[Southold Car Rentals](https://expedia.ca/Car-Rentals-In-Southold.d183719.Car-Rental-Guide) ![](https://images.trvl-media.com/place/183719/763c5957-1d09-4b50-be9f-256173572489.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Southold 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 Southold Vacation The coastal scenery and rich history are just the beginning of the things Southold has going for it. Experience the very best of this interesting city your way with a customized Southold vacation package. [67 Steps Beach](https://www.expedia.ca/67-Steps-Beach-Greenport.d553248626388140598.Vacation-Attraction), [Raphael Winery](https://www.expedia.ca/Raphael-Winery-Peconic.d6327146.Vacation-Attraction) and [Railroad Museum of Long Island](https://www.expedia.ca/Railroad-Museum-Of-Long-Island-Pipes-Cove.d6327144.Vacation-Attraction) are just some of the many sights worth checking out during your trip to Southold. A few quick clicks is all it takes to put together your ideal Southold vacation on Expedia. ## Top Southold Vacation Deals Price found within the past 48 hours. Click for updated prices. ![The Ridge Hotel](https://images.trvl-media.com/lodging/2000000/1790000/1785000/1784927/28d93ae4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Ridge Hotel Manhattan CA $1,367 per person Jun 8 - Jun 14 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Newark Liberty Intl. Airport (EWR) 8.2/10 Very Good! (1,032 reviews) Room small but clean. Staff were great, friendly and helpful. Reviewed on Mar 21, 2026 ![1 Hotel Brooklyn Bridge](https://images.trvl-media.com/lodging/16000000/15400000/15399700/15399642/b1e6b86c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel Brooklyn Bridge CA $1,812 per person Jun 19 - Jun 21 found 13 hours ago Roundtrip flight included Toronto (YYZ) to Newark Liberty Intl. Airport (EWR) 8.8/10 Excellent! (1,000 reviews) Excellent staff, clean room, fantastic onsite restaurants. Reviewed on Mar 10, 2026 ![The Fifth Avenue Hotel](https://images.trvl-media.com/lodging/97000000/96480000/96472700/96472655/183802ec_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Fifth Avenue Hotel Manhattan CA $2,050 per person Jun 8 - Jun 11 found 1 day ago Roundtrip flight included Toronto (YTO) to Newark Liberty Intl. Airport (EWR) 9.6/10 Exceptional! (196 reviews) Absolutely everything. Amazingly appointed room, very friendly stafff. Reviewed on Mar 1, 2026 ![Arthouse Hotel New York City](https://images.trvl-media.com/lodging/1000000/20000/12200/12117/0e6cbb94_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Arthouse Hotel New York City Manhattan CA $1,662 per person Jun 8 - Jun 14 found 19 hours ago Roundtrip non-stop flight included Hamilton (YHM) to Newark Liberty Intl. Airport (EWR) 8.8/10 Excellent! (1,843 reviews) Wish there were fridges in all of the rooms. Front desk were super polite and helpful. Reviewed on Mar 25, 2026 ![Park Central Hotel New York](https://images.trvl-media.com/lodging/1000000/10000/4200/4164/cb48c512_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Central Hotel New York Manhattan CA $1,595 per person Jun 8 - Jun 14 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Newark Liberty Intl. Airport (EWR) 7.6/10 Good! (3,962 reviews) This property certainly has lost its charm Reviewed on Mar 25, 2026 ## Ready to book your vacation to Southold? Choose your dates ## Southold Hotel Deals ![The Shoals Suites and Slips](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/5a27472c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Shoals Suites and Slips 61600 Main Rd Southold NY CA $211 CA $276 total Apr 23 - Apr 24 includes taxes & fees 9.4/10 Exceptional! (250 reviews) Clean, spacious and thoughtful room amenities. Close by to town and great restaurants. Reviewed on Mar 23, 2026 [](https://expedia.ca/Hotel-Search?startDate=23%2F04%2F2026&endDate=24%2F04%2F2026&selected=76716269&PinnedHotelID=76716269&HadPinnedHotel=true®ionId=183719) ![Vine & Sand](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/242d28e0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Vine & Sand 47100 New York 25 Southold NY 9.8/10 Exceptional! (16 reviews) Location was perfect for visiting the wineries… breakfast was to die for! Reviewed on Mar 22, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=08%2F04%2F2026&endDate=09%2F04%2F2026&selected=96718085&PinnedHotelID=96718085&HadPinnedHotel=true®ionId=183719) [](https://expedia.ca/Hotel-Search?startDate=08%2F04%2F2026&endDate=09%2F04%2F2026&selected=96718085&PinnedHotelID=96718085&HadPinnedHotel=true®ionId=183719) ![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/fc6ee41c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Water's Edge Resort & Spa 1525 Boston Post Road Westbrook CT Fully refundableReserve now, pay when you stay CA $292 CA $360 total Mar 29 - Mar 30 includes taxes & fees 8.8/10 Excellent! (1,007 reviews) The room was perfect, staff was excellent, parking was right next to my room. Best Breakfast Sausage ever. Reviewed on Mar 24, 2026 [](https://expedia.ca/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=9679841&PinnedHotelID=9679841&HadPinnedHotel=true®ionId=183719) [See all 4,386 properties in Southold](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=26%2F03%2F2026&endDate=27%2F03%2F2026®ionId=183719) 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) ### What to do in Southold ![great fun with friends](https://mediaim.expedia.com/localexpert/48383244/3ee3321d-c1fe-4916-b148-b5bc474f2489.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Full Day Private Long Island Wine Tours from New York City CA $259 per adult [](https://expedia.ca/things-to-do/full-day-private-long-island-wine-tours-from-new-york-city.a48383244.activity-details) [See all activities in Southold](https://expedia.ca/things-to-do/search?rid=183719) ## 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