Title: Southold Holidays 2025 from $743 | 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/183719/81468873-e891-4a92-aa0d-1938572ea198.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Southold Holidays from £1,054 ## Book a Hotel + Flight or Car together to unlock savings Photo by Benny Goh - ## 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. ![Hotel Seville Nomad, in the Unbound Collection by Hyatt](https://images.trvl-media.com/lodging/18000000/17940000/17939200/17939186/186b385b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Seville Nomad, in the Unbound Collection by Hyatt Manhattan £1,054 per person 24 Nov - 28 Nov found 24 hours ago Return direct flight included Glasgow (GLA) to New York (JFK) 8.6/10 Excellent! (1,103 reviews) Tired small room. In desperate need of refurbishment. Similar much of common parts. Reviewed on 12 Sept 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-11-24/2025-11-28/?FromAirport=GLA&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=17939186&paandie=true&dealMarker=TaaQratrqqnZ1bEWc0Hb0wa-6EsqobrjoWyaIghcqcEeGlc_yxQBJvL_bGP4ngRr) ![Fitzpatrick Grand Central](https://images.trvl-media.com/lodging/1000000/120000/119300/119276/8fddb8d1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fitzpatrick Grand Central Manhattan £1,259 per person 21 Oct - 25 Oct found 1 day ago Return flight included London (LHR) to New York (JFK) 9/10 Wonderful! (1,001 reviews) Great location and friendly staff Reviewed on 7 Sept 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-10-21/2025-10-25/?FromAirport=LHR&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=119276&paandie=true&dealMarker=h98wHu3bKEb5YBR6b3rjGjpuELvnFJ4qMOIS0oBbweCFzMRgC54RW_odrBr_RIh0) ![The Standard East Village](https://images.trvl-media.com/lodging/3000000/2180000/2175500/2175451/4984467e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Standard East Village Manhattan £1,454 per person 21 Oct - 25 Oct found 1 day ago Return flight included London (LHR) to New York (JFK) 9/10 Wonderful! (1,009 reviews) Absolutely the best stay in NY! A bit pricy but worth every single cent I paid! Excellent staff who actually care about you as a guest of The Standard. Definitely will return! Reviewed on 16 Sept 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-10-21/2025-10-25/?FromAirport=LHR&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2175451&paandie=true&dealMarker=h98wHu3bKEb5YBR6b3rjGn0KhY4YGwhDrfGdyg7WHZLY8MRPox89AZi8t__zKsuv) ![The Draper New York, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/49000000/48630000/48621800/48621748/f5ade294_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Draper New York, Tapestry Collection by Hilton Manhattan £1,325 per person 21 Oct - 25 Oct found 1 day ago Return flight included London (LHR) to New York (JFK) 8.8/10 Excellent! (985 reviews) Great location in Midtown! The room was nice and cold when we arrived on a warmer day, so that was lovely. The space is very small, no counter space in bathroom, but typical of NYC in my experience. There was a water refill station on the C floor and a bathroom. :) Reviewed on 17 Sept 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-10-21/2025-10-25/?FromAirport=LHR&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=48621748&paandie=true&dealMarker=h98wHu3bKEb5YBR6b3rjGjpuELvnFJ4qMOIS0oBbweCa8_wRt6Hf2XNe_JhmsMwz) ![Courtyard New York Manhattan/ Midtown East](https://images.trvl-media.com/lodging/1000000/160000/151300/151297/e587ffba_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Courtyard New York Manhattan/ Midtown East Manhattan £1,384 per person 21 Oct - 25 Oct found 1 day ago Return flight included London (LHR) to New York (JFK) 9/10 Wonderful! (2,292 reviews) This was a last minute trip, so lodging options were limited. The Courtyard is ideally located in Midtown. If you are looking for a lush green environment, you won’t be happy here. However, keep in mind that Central Park is just a skip and hop away. Besides, you are in Manhattan, so 90% of the places will have you looking onto another building. There is a convenient subway entrance across the street serving R and E lines. There are not so many dining options - you have to walk a couple of blocks, but that is not a big deal. Reviewed on 17 Sept 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-10-21/2025-10-25/?FromAirport=LHR&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=151297&paandie=true&dealMarker=h98wHu3bKEb5YBR6b3rjGn0KhY4YGwhDrfGdyg7WHZKxdQsjJVYfwzrmpcKTPOXF) ## 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/77000000/76720000/76716300/76716269/968755d8_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Shoals Suites and Slips 61600 Main Rd, Southold, NY £207 24 Sept - 25 Sept includes taxes & fees 9.4/10 Exceptional! (204 reviews) "Staff was very helpful. We arrived late and had no problems getting into our room. The breakfast was awesome- lots of options and they even kept it open a little longer to accommodate our schedule. Great stay!" Reviewed on 12 Sept 2025 [](https://expedia.co.uk/Hotel-Search?startDate=24%2F09%2F2025&endDate=25%2F09%2F2025&selected=76716269&PinnedHotelID=76716269&HadPinnedHotel=true®ionId=183719) ![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sound View Greenport 58775 County Rd 48, Greenport, NY £265 22 Sept - 23 Sept includes taxes & fees 8.4/10 Very Good! (569 reviews) Wonderful but the bathroom is too small "We loved our stay. It’s like a motel turned eco friendly resort. We had an upper corner room, which afforded us unobstructed views and privacy. The bed was so comfortable and the room was spacious—except for the bathroom. The bathroom needs vanity space! While the charm of this place is partly due ..." Reviewed on 7 Sept 2025 [](https://expedia.co.uk/Hotel-Search?startDate=22%2F09%2F2025&endDate=23%2F09%2F2025&selected=15273178&PinnedHotelID=15273178&HadPinnedHotel=true®ionId=183719) ![Greenview Inn Riverhead](https://images.trvl-media.com/lodging/2000000/1380000/1374000/1373980/302832e1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Greenview Inn Riverhead 1433 W Main St, Riverhead, NY Fully refundableReserve now, pay when you stay 7.2/10 Good! (728 reviews) Great stay! "We don’t usually stay at motels. But these rooms were very, very nice and well designed. They were cute! The motel staff were friendly and accommodating." Reviewed on 1 Sept 2025 [Get rates](https://expedia.co.uk/Hotel-Search?startDate=02%2F10%2F2025&endDate=03%2F10%2F2025&selected=1373980&PinnedHotelID=1373980&HadPinnedHotel=true®ionId=183719) [](https://expedia.co.uk/Hotel-Search?startDate=02%2F10%2F2025&endDate=03%2F10%2F2025&selected=1373980&PinnedHotelID=1373980&HadPinnedHotel=true®ionId=183719) [See all 4,319 properties in Southold](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=19%2F09%2F2025&endDate=20%2F09%2F2025®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 ![Join a small group full-day wine tour with a certified Sommelier host](https://mediaim.expedia.com/localexpert/1350908/45c47e3f-3e0f-448e-a1a4-64596ec183f0.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Long Island Wine and Food Day Trip with Sommelier host from NYC £110 per adult [](https://expedia.co.uk/things-to-do/long-island-wine-and-food-day-trip-with-sommelier-host-from-nyc.a1350908.activity-details) ![Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting](https://mediaim.expedia.com/localexpert/48343602/e3615e6b-a5d4-472f-b85c-80434f787622.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### From Mattituck: North Fork Area Bike Tour with Food Tasting £103 per adult [](https://expedia.co.uk/things-to-do/from-mattituck-north-fork-area-bike-tour-with-food-tasting.a48343602.activity-details) [See all activities in Southold](https://expedia.co.uk/things-to-do/search?rid=183719) ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - Other ### Accommodation - [5 Star Hotels in Hamptons](https://www.expedia.co.uk/5Star-Hamptons-Hotels.s50-0-d6056452.Travel-Guide-Filter-Hotels) - [Bay Point Hotels](https://www.expedia.co.uk/Bay-Point-Sag-Harbor-Hotels.0-n553248635976471151-0.Travel-Guide-Filter-Hotels) - [Cutchogue Hotels](https://www.expedia.co.uk/Cutchogue-Hotels.d183659.Travel-Guide-Hotels) - [Town of Southold Town Hotels](https://www.expedia.co.uk/Destinations-In-Town-Of-Southold-Town.d553248635976002319.Hotel-Destinations) - [East Marion Hotels](https://www.expedia.co.uk/East-Marion-Hotels.d6069914.Travel-Guide-Hotels) - [Hotels near Gardiner's Bay Country Club](https://www.expedia.co.uk/Gardiners-Bay-Country-Club-Hotels.0-l6282173-0.Travel-Guide-Filter-Hotels) - [Beach Resorts & in Greenport](https://www.expedia.co.uk/Greenport-Hotels-Beach-Hotels.0-0-d110728-tBeachHotels.Travel-Guide-Filter-Hotels) - [Greenport Hotels](https://www.expedia.co.uk/Greenport-Hotels.d110728.Travel-Guide-Hotels) - 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[Hamptons Holidays](https://www.expedia.co.uk/Hamptons.d6056452.Holidays-City-Breaks) - [Visit Hamptons](https://www.expedia.co.uk/Hamptons.dx6056452) - [Havens House](https://www.expedia.co.uk/Havens-House-Shelter-Island.d6232745.Attraction) - [Home Sweet Home Museum](https://www.expedia.co.uk/Home-Sweet-Home-Museum-East-Hampton.d6326918.Attraction) - [Indian Island County Park Holidays](https://www.expedia.co.uk/Indian-Island-County-Park.d6224460.Holidays-City-Breaks) - [Island's End Golf and Country Club](https://www.expedia.co.uk/Islands-End-Golf-And-Country-Club-East-Marion.d6326920.Attraction) - [Longhouse Reserve](https://www.expedia.co.uk/LongHouse-Reserve-East-Hampton.d6326942.Attraction) - [Mccall Wines](https://www.expedia.co.uk/McCall-Wines-Cutchogue.d553248621532665592.Attraction) - [Visit New Suffolk](https://www.expedia.co.uk/New-Suffolk.dx3000449151) - [New York Holidays](https://www.expedia.co.uk/New-York.d178293.Holidays-City-Breaks) - [Old Hook Mill](https://www.expedia.co.uk/Old-Hook-Mill-North-Main-Street-Historic-District.d6064493.Attraction) - [Osborn - Jackson House Museum](https://www.expedia.co.uk/Osborn-Jackson-House-Museum-East-Hampton.d6064495.Attraction) - [Parrish Art Museum](https://www.expedia.co.uk/Parrish-Art-Museum-Water-Mill.d6326954.Attraction) - [Pollock-Krasner House and Study Center](https://www.expedia.co.uk/Pollock-Krasner-House-And-Study-Center-East-Hampton.d6064485.Attraction) - [Sag Harbor Holidays](https://www.expedia.co.uk/Sag-Harbor.d154327.Holidays-City-Breaks) - [Visit Sag Harbor](https://www.expedia.co.uk/Sag-Harbor.dx154327) - [Sagaponack Holidays](https://www.expedia.co.uk/Sagaponack.d3000449529.Holidays-City-Breaks) - [Shelter Island Historical Society](https://www.expedia.co.uk/Shelter-Island-Historical-Society-Shelter-Island.d553248635961235094.Attraction) - [Visit Shelter Island](https://www.expedia.co.uk/Shelter-Island.dx157359) - [Shinnecock Hills Golf Course](https://www.expedia.co.uk/Shinnecock-Hills-Golf-Course-Southampton.d6327546.Attraction) - [Southampton Arts Center](https://www.expedia.co.uk/Southampton-Arts-Center-Southampton.d553248629501562732.Attraction) - [Southampton Cultural Center](https://www.expedia.co.uk/Southampton-Cultural-Center-Southampton.d553248621558565665.Attraction) - [Southampton Historical Museum](https://www.expedia.co.uk/Southampton-Historical-Museum-Southampton.d6327587.Attraction) - [Southampton Holidays](https://www.expedia.co.uk/Southampton.d6782.Holidays-City-Breaks) - [Sunset Beach](https://www.expedia.co.uk/Sunset-Beach-Shelter-Island-Heights.d553248626388141313.Attraction) - [Wainscott Holidays](https://www.expedia.co.uk/Wainscott.d6046784.Holidays-City-Breaks) - [Wolffer Estates Vineyard](https://www.expedia.co.uk/Wolffer-Estates-Vineyard-Sagaponack.d6064497.Attraction) - [All inclusive Holiday Packages Hamptons](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/6056452/Hamptons) ### Cars - [Car hire Cutchogue](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Cutchogue.d183659.Car-Hire-Guide) - [Car hire Greenport](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Greenport.d110728.Car-Hire-Guide) - [Car hire near Hamptons](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Hamptons.d6056452.Car-Hire-Guide) - [Car hire Orient](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Orient.d6326191.Car-Hire-Guide) - [Car hire Sag Harbor](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Sag-Harbor.d154327.Car-Hire-Guide) - [Convertible Car Hire in Hamptons](https://www.expedia.co.uk/Convertible-Car-Rentals-In-Hamptons.d6056452-tConvertible.Car-Rental-Guide-Class) - [Luxury Car Hire in Hamptons](https://www.expedia.co.uk/Luxury-Car-Rentals-In-Hamptons.d6056452-tLuxury.Car-Rental-Guide-Class) - [Minivan Car Hire in Shelter Island](https://www.expedia.co.uk/Minivan-Car-Rentals-In-Shelter-Island.d157359-tMinivan.Car-Rental-Guide-Class) - [Sixt Rental Cars in Hamptons](https://www.expedia.co.uk/Sixt-Car-Rentals-In-Hamptons.d6056452-c35.Car-Rental-Guide-Suppliers) ### Holiday Homes - [East Marion Holiday Rentals](https://www.expedia.co.uk/East-Marion-Holiday-Rentals.d6069914.Travel-Guide-HolidayRentals) - [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) ### Other - [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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