Title: Southold Holiday Packages | Highly Recommended Packages 2026 | Expedia.co.uk [Hotels in Southold](https://expedia.co.uk/Southold-Hotels.d183719.Travel-Guide-Hotels)[Holiday Rentals in Southold](https://expedia.co.uk/Southold-Holiday-Rentals.d183719.Travel-Guide-HolidayRentals)[Southold Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Southold.d183719.Car-Hire-Guide) ![](https://images.trvl-media.com/place/183719/763c5957-1d09-4b50-be9f-256173572489.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Southold Holidays from £1,293 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to £335 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 Packages with flights are ATOL protected #### Your Southold Holiday 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 customised Southold holiday package. [67 Steps Beach](https://www.expedia.co.uk/67-Steps-Beach-Greenport.d553248626388140598.Attraction), [Raphael Winery](https://www.expedia.co.uk/Raphael-Winery-Peconic.d6327146.Attraction) and [Railroad Museum of Long Island](https://www.expedia.co.uk/Railroad-Museum-Of-Long-Island-Pipes-Cove.d6327144.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 holiday on Expedia. ## Top Southold Flight + Hotel Deals Price found within the past 48 hours. Click for updated prices. ![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 £1,293 per person 22 May - 29 May found 1 day ago Return flight included Edinburgh (EDI) to Newark Liberty Intl. Airport (EWR) 7.6/10 Good! (3,962 reviews) i love the location and the staff go above and beyond. Elas is great to help Reviewed on 21 Mar 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 Save 100% on your flight £1,997 per person 30 Apr - 5 May found 1 day ago Return direct flight included Manchester (MAN) to Newark Liberty Intl. Airport (EWR) 8.8/10 Excellent! (1,000 reviews) Excellent staff, clean room, fantastic onsite restaurants. Reviewed on 10 Mar 2026 ![Hotel Riu Plaza Manhattan Times Square](https://images.trvl-media.com/lodging/61000000/60680000/60677500/60677495/0bd08347_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Manhattan Times Square Manhattan Save 100% on your flight £1,657 per person 22 May - 29 May found 1 day ago Return flight included Edinburgh (EDI) to Newark Liberty Intl. Airport (EWR) 9.2/10 Wonderful! (3,450 reviews) Great gym, beautiful lobby, nice bell service. Staff was a little rude when informing us that no outside food may be consumed in the lobby. For the price we pay for the hotel stay, we would have expected a more courteous approach. Reviewed on 21 Mar 2026 ![The Plaza - A Fairmont Managed Hotel](https://images.trvl-media.com/lodging/1000000/30000/28100/28044/1419565f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Plaza - A Fairmont Managed Hotel Manhattan Save 100% on your flight £3,598 per person 7 May - 12 May found 7 hours ago Return flight included London (LON) to Newark Liberty Intl. Airport (EWR) 9/10 Wonderful! (1,009 reviews) Absolutely AMAZING in every way. The Plaza exceeded my expectations and was central in making our engagement weekend a time that we will always remember! The STAFF are what truly sets the Plaza apart. Always helpful, humorous and posh without being stuffy, the staff truly are the soul of the institution. Reviewed on 17 Mar 2026 ![Hotel Riu Plaza New York Times Square](https://images.trvl-media.com/lodging/12000000/11680000/11677800/11677770/136f5a69_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza New York Times Square Manhattan £1,306 per person 14 May - 18 May found 1 day ago Return direct flight included Birmingham (BHX) to Newark Liberty Intl. Airport (EWR) 9/10 Wonderful! (2,931 reviews) Very clean hotel room and friendly, helpful staff. Having breakfast readily available every morning was wonderful. We are so glad we stayed with the Riu Times Square for our first time in New York City! Reviewed on 20 Mar 2026 ## Southold Essential Information | Language | English | | --------------- | ---------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Closest Airport | Tweed - New Haven Regional Airport (HVN) | | Population | 5,700 | | Max Temp Winter | 4ºC | | Max Temp Summer | 24ºC | | Top Sights | [67 Steps Beach](https://www.expedia.co.uk/67-Steps-Beach-Greenport.d553248626388140598.Attraction), [Macari Vineyards](https://www.expedia.co.uk/Macari-Vineyards-Mattituck.d6326944.Attraction) and [Kontokosta Winery](https://www.expedia.co.uk/Kontokosta-Winery-Greenport.d6326928.Attraction) | ## Top hotels in Southold ![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 £128 29 Mar - 30 Mar includes taxes & fees 9.4/10 Exceptional! (245 reviews) Fine Reviewed on 15 Mar 2026 [](https://expedia.co.uk/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%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 9.6/10 Exceptional! (15 reviews) Vine + Sand was wonderful. The hosts were so friendly and it was close to many wineries. Reviewed on 19 Jan 2026 [Get rates](https://expedia.co.uk/Hotel-Search?startDate=04%2F04%2F2026&endDate=05%2F04%2F2026&selected=96718085&PinnedHotelID=96718085&HadPinnedHotel=true®ionId=183719) [](https://expedia.co.uk/Hotel-Search?startDate=04%2F04%2F2026&endDate=05%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 £180 23 Mar - 24 Mar includes taxes & fees 8.8/10 Excellent! (1,001 reviews) Easy Reviewed on 21 Mar 2026 [](https://expedia.co.uk/Hotel-Search?startDate=23%2F03%2F2026&endDate=24%2F03%2F2026&selected=9679841&PinnedHotelID=9679841&HadPinnedHotel=true®ionId=183719) [See all 4,375 properties in Southold](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=22%2F03%2F2026&endDate=23%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 Holidays [](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.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 Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click) ![gay friendly holidays](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Holidays [](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Holidays [](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Pet Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click) ![Holiday in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.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 £140 per adult [](https://expedia.co.uk/things-to-do/full-day-private-long-island-wine-tours-from-new-york-city.a48383244.activity-details) [See all activities in Southold](https://expedia.co.uk/things-to-do/search?rid=183719) ## Explore a world of travel with Expedia - 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[Hamptons Holiday Rentals ](https://www.expedia.co.uk/Hamptons-Holiday-Rentals.d6056452.Travel-Guide-HolidayRentals) - [Mattituck Holiday Rentals ](https://www.expedia.co.uk/Mattituck-Holiday-Rentals.d6223780.Travel-Guide-HolidayRentals) - [New Suffolk Holiday Rentals ](https://www.expedia.co.uk/New-Suffolk-Holiday-Rentals.d3000449151.Travel-Guide-HolidayRentals) - [Sag Harbor Holiday Rentals ](https://www.expedia.co.uk/Sag-Harbor-Holiday-Rentals.d154327.Travel-Guide-HolidayRentals) - [Shelter Island Heights Holiday Rentals ](https://www.expedia.co.uk/Shelter-Island-Heights-Holiday-Rentals.d183716.Travel-Guide-HolidayRentals) - [Shelter Island Holiday Rentals ](https://www.expedia.co.uk/Shelter-Island-Holiday-Rentals.d157359.Travel-Guide-HolidayRentals) - [Things to do in Hamptons ](https://www.expedia.co.uk/Things-To-Do-In-Hamptons.d6056452.Travel-Guide-Activities) - [Things to do in Mattituck ](https://www.expedia.co.uk/Things-To-Do-In-Mattituck.d6223780.Travel-Guide-Activities) - [Things to do in Sag Harbor ](https://www.expedia.co.uk/Things-To-Do-In-Sag-Harbor.d154327.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. 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