Title: 5 Stars Hotels in Southold, New York from CA $389 - Find Cheap Southold Hotels With 5 Stars | Expedia.ca [Southold Travel Guide](https://expedia.ca/Southold.dx183719)[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)[Things to do in Southold](https://expedia.ca/Things-To-Do-In-Southold.d183719.Travel-Guide-Activities)[Southold Car Rentals](https://expedia.ca/Car-Rentals-In-Southold.d183719.Car-Rental-Guide)[Southold Vacation Packages](https://expedia.ca/Southold.d183719.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/2af9844708ff5148df98a90729e7edaf.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 5 Stars Hotels in Southold, New York from CA $389 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Southold 5 Star Hotels Tonight [Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-10-29&endDate=2025-10-30&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 30 - Oct 31](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-10-30&endDate=2025-10-31&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-10-31&endDate=2025-11-02&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-11-07&endDate=2025-11-09&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Southold 5 Star Hotels ![Front of property - evening/night](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/e0e0def6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Graybarn Cottage | Terrace/patio](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/1f2aee03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Graybarn Cottage | Living area](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/1fbed560.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Graybarn Cottage | Room amenity](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/1d639007.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mill House Inn North Main Street Historic District 9.0/10 Wonderful (70) "Great experience at a wonderful property!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian CA $453 CA $570 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/East-Hampton-Hotels-Mill-House-Inn.h2861838.Hotel-Information) ![House | Outdoor pool](https://images.trvl-media.com/lodging/33000000/32420000/32411100/32411044/23f4590c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House | Front of property](https://images.trvl-media.com/lodging/33000000/32420000/32411100/32411044/61df3ce6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/33000000/32420000/32411100/32411044/a4e472c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House | Staircase](https://images.trvl-media.com/lodging/33000000/32420000/32411100/32411044/96fc375c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa Newmark Holiday home 7 BestStayz.1 Sagaponack [](https://www.expedia.ca/Sagaponack-Hotels-Casa-Newmark-Holiday-Home-7-BestStayz1.h32411044.Hotel-Information) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Southold-Hotels.s50-0-d183719.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Southold-Hotels.s50-0-d183719.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Southold. ![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Sound View Greenport 58775 County Rd 48, Greenport, NY CA $281 CA $389 total Nov 11 - Nov 12 includes taxes & fees 8.4/10 Very Good! (584 reviews) [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Madison Beach Hotel](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/18df186b_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Madison Beach Hotel 94 West Wharf Road, Madison, CT CA $342 CA $393 total Nov 13 - Nov 14 includes taxes & fees 9.4/10 Exceptional! (326 reviews) [](https://expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.Hotel-Information) ![Journey East Hampton](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/acd2c1de_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Journey East Hampton 490 Pantigo Road, East Hampton, NY CA $320 CA $402 total Nov 2 - Nov 3 includes taxes & fees 9/10 Wonderful! (154 reviews) [](https://expedia.ca/East-Hampton-Hotels-Journey-East-Hampton.h23252049.Hotel-Information) Still don't see what you're looking for? [See all properties in Southold.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F10%2F2025&endDate=31%2F10%2F2025®ionId=183719&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F10%2F2025&endDate=31%2F10%2F2025®ionId=183719&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F10%2F2025&endDate=31%2F10%2F2025®ionId=183719&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F10%2F2025&endDate=31%2F10%2F2025®ionId=183719&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F10%2F2025&endDate=31%2F10%2F2025®ionId=183719&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F10%2F2025&endDate=31%2F10%2F2025®ionId=183719&star=50&star=50&amenities=WATER_PARK) 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. ## Learn more about Southold Vineyards and farm stands dot the landscape of this North Fork gem, inviting visitors to sample local wines and fresh produce. Stroll along the pebble beaches, explore historic lighthouses, or take a ferry to nearby Shelter Island for a day trip. [See all hotels in Southold](https://www.expedia.ca/Hotel-Search?startDate=2025-11-12&endDate=2025-11-13&adults=2®ionId=183719) ![Day trip to North Fork wineries. Stopped at this beach for a break before driving back to the city. #sunset #nature #wanderlust #waterlust #beach #colorful #citylife #NikonD7100 #Manfratto tripod. ](https://images.trvl-media.com/place/183719/81468873-e891-4a92-aa0d-1938572ea198.jpg?impolicy=fcrop&w=899&h=600&p=1&q=high) Photo by Benny Goh ## Top Southold Hotel Reviews ## Find out more about Southold ## Five Star Hotels in Southold There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Southold so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Southold and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Southold Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places. Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town. #### Make Your Escape to Southold The results are in, and Southold 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Southold! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Southold today and settle down in the lap of luxury tomorrow. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Southold? > You can find many different pricing options for 5-star hotels in Southold on Expedia. The amount you pay will depend on your vacation dates, length of stay and other factors. Compare available properties for your desired dates and make use of our pricing and other filters to find the perfect upscale stay. > > > > - Search for the lowest price per night from CA $389 ### What makes a hotel 5 stars in Southold? > Faultless guest service is the foundation of every 5-star hotel in Southold. From the minute you arrive, staff attend to your every need, whether arranging valet parking or providing in-room massages. In addition, hotels have to offer superior conveniences to obtain a 5-star rating. These can include luxury toiletries, spa facilities, swimming pools, gastronomic kitchens and knowledgeable concierge. ### Are there any 5-star all-inclusive resorts in Southold? > Use our handy filters to find an upscale retreat in Southold where everything you need is included. Next, narrow down your results for accommodations that have a rating of 5 stars and are categorized as "All inclusive." The most important thing on the agenda at these stays? 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[Shelter Island Hotels](https://www.expedia.ca/Shelter-Island-Hotels.d157359.Travel-Guide-Hotels) - [Houseboats in Shelter Island](https://www.expedia.ca/Shelter-Island-Houseboats.d157359-aaHouseboats.Travel-Guide-Accommodation) - [Resorts in Shelter Island](https://www.expedia.ca/Shelter-Island-Resort-Hotels.d157359-aaResortHotels.Travel-Guide-Accommodation) - [Adults Only Resorts & in Silver Beach](https://www.expedia.ca/Silver-Beach-Shelter-Island-Hotels-Adults-Only-Resorts.0-n553248635976481903-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Silver Beach Hotels](https://www.expedia.ca/Silver-Beach-Shelter-Island-Hotels.0-n553248635976481903-0.Travel-Guide-Filter-Hotels) - [Hotels near Sunset Beach](https://www.expedia.ca/Sunset-Beach-Hotels.0-l553248626388141313-0.Travel-Guide-Filter-Hotels) - [The Heights Hotels](https://www.expedia.ca/The-Heights-Shelter-Island-Heights-Hotels.0-n553248635976473534-0.Travel-Guide-Filter-Hotels) - [Flights to Greenport](https://www.expedia.ca/Cheap-Flights-To-Greenport.d110728.Travel-Guide-Flights) - [Flights to Shelter Island](https://www.expedia.ca/Cheap-Flights-To-Shelter-Island.d157359.Travel-Guide-Flights) - [Flights from Shelter Island](https://www.expedia.ca/lp/flights/157359/flights-from-shelter-island) - [Flights from Toronto (YYZ) to New York (NYC)](https://www.expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york) - [Bedell Cellars](https://www.expedia.ca/Bedell-Cellars-Cutchogue.d553248621532665643.Vacation-Attraction) - [Visit Pipes Cove](https://www.expedia.ca/Greenport-Pipes-Cove.dx553248635976473295) - [Pindar Vineyards](https://www.expedia.ca/Pindar-Vineyards-Peconic.d6326965.Vacation-Attraction) - [Shelter Island Heights Vacations](https://www.expedia.ca/Shelter-Island-Heights.d183716.Destination-Travel-Guides) - [Visit Shelter Island](https://www.expedia.ca/Shelter-Island.dx157359) - [Car rental Greenport](https://www.expedia.ca/Car-Rentals-In-Greenport.d110728.Car-Rental-Guide) - [Car rental Shelter Island](https://www.expedia.ca/Car-Rentals-In-Shelter-Island.d157359.Car-Rental-Guide) - [Shelter Island Vacation Rentals](https://www.expedia.ca/Shelter-Island-Vacation-Rentals.d157359.Travel-Guide-VacationRentals) - [Things to do in Greenport](https://www.expedia.ca/Things-To-Do-In-Greenport.d110728.Travel-Guide-Activities) - [Things to do in Shelter Island Heights](https://www.expedia.ca/Things-To-Do-In-Shelter-Island-Heights.d183716.Travel-Guide-Activities) - [Things to do in Shelter Island](https://www.expedia.ca/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities) - [Book 5 Star Hotels in Southold on Expedia.com](https://www.expedia.com/5Star-Southold-Hotels.s50-0-d183719.Travel-Guide-Filter-Hotels)