Title: Visit Southold: Best of Southold Tourism | Expedia Travel Guide - 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)[Southold Vacation Packages](https://expedia.ca/Southold.d183719.Destination-Travel-Guides) # Southold ## Travel Guide ![Southold](https://mediaim.expedia.com/destination/1/2af9844708ff5148df98a90729e7edaf.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Photo by Benny Goh ](https://mediaim.expedia.com/destination/2/0b7d297c814bcafdcca769aaf161b02d.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Benny Goh](https://mediaim.expedia.com/destination/2/0b7d297c814bcafdcca769aaf161b02d.jpg) ![Photo by Benny Goh ](https://mediaim.expedia.com/destination/2/2f13689962fec234bbb84efa177f6d3f.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Benny Goh](https://mediaim.expedia.com/destination/2/2f13689962fec234bbb84efa177f6d3f.jpg) ![Photo by 4 Star Traveler](https://mediaim.expedia.com/destination/2/3f9e84132c7cf86c180b2490717bed52.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by 4 Star Traveler](https://mediaim.expedia.com/destination/2/3f9e84132c7cf86c180b2490717bed52.jpg) ![Photo by 4 Star Traveler](https://mediaim.expedia.com/destination/2/f64d2cccd6875c3f98fea2c3d4ef6714.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by 4 Star Traveler](https://mediaim.expedia.com/destination/2/f64d2cccd6875c3f98fea2c3d4ef6714.jpg) ## Visit Southold Things to do - Southold Hotel Deals - Vacation Rentals 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 CA $307 CA $386 total Oct 13 - Oct 14 includes taxes & fees Stay at this 3.5-star hotel in Southold. Enjoy free WiFi, free bicycles on site, and a business center. Our guests praise the helpful staff in our reviews. Popular ... 9.4/10 Exceptional! (210 reviews) "Great place, beautiful views! I’ll be back." Reviewed on Oct 6, 2025 [](https://expedia.ca/Hotel-Search?startDate=13%2F10%2F2025&endDate=14%2F10%2F2025&selected=76716269&PinnedHotelID=76716269&HadPinnedHotel=true®ionId=183719) ![Pier Blue Inn Old Saybrook - Essex](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Pier Blue Inn Old Saybrook - Essex 1430 Boston Post Rd, Old Saybrook, CT CA $112 CA $128 total Oct 8 - Oct 9 includes taxes & fees Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ... 7.8/10 Good! (1,005 reviews) "For a budget hotel its not bad - area is generally pricy - its just needs a facelift - it needs to remove the carpets. Staff is nice." Reviewed on Oct 4, 2025 [](https://expedia.ca/Hotel-Search?startDate=08%2F10%2F2025&endDate=09%2F10%2F2025&selected=12143&PinnedHotelID=12143&HadPinnedHotel=true®ionId=183719) ![Quality Inn Old Saybrook - Westbrook](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Quality Inn Old Saybrook - Westbrook 100 Essex Rd, Old Saybrook, CT CA $130 CA $150 total Nov 2 - Nov 3 includes taxes & fees Book a stay at this business-friendly hotel in Old Saybrook. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ... 7.6/10 Good! (1,003 reviews) "Overall, a nice hotel for a one day trip! :)" Reviewed on Oct 5, 2025 [](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=3988&PinnedHotelID=3988&HadPinnedHotel=true®ionId=183719) [See all 4,312 properties in Southold](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=08%2F10%2F2025&endDate=09%2F10%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. ![Fabulous Waterfront Property in the Heart of Wine Country](https://images.trvl-media.com/lodging/34000000/33510000/33504800/33504750/10ac0400_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Fabulous Waterfront Property in the Heart of Wine Country Peconic Book a stay at this family-friendly cottage in Southold. Enjoy free WiFi, a water park, and a garden. Popular attractions Goldsmith's Inlet Park and Sannino's ... 9.8/10 Exceptional! (172 reviews) "Great place and beautiful scenery" Reviewed on Aug 31, 2025 [](https://expedia.ca/Peconic-Hotels-Fabulous-Waterfront-Property-In-The-Heart-Of-Wine-Country.h33504750.Hotel-Information) ![Beautifully farmhouse](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/10ef3e76_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Beautifully farmhouse Southold Book a stay at this family-friendly vacation home in Southold. Enjoy free WiFi, a water park, and a garden. Popular attractions Sparkling Pointe and The Old ... 10/10 Exceptional! (2 reviews) "We spent a few days to attend a family wedding. We were 7 and the house was extremely comfortable for all of us. The house is 2 floors and there is no bathroom upstairs so keep that in mind when assigning sleeping arrangements. We found a well stocked welcome basket and a bottle of wine which were ..." Reviewed on Sep 8, 2025 [](https://expedia.ca/Southold-Hotels-Magic-Place.h113098265.Hotel-Information) ![Windward Shores Ocean Resort](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/23c43d21_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Windward Shores Ocean Resort 2062 Montauk Highway, PO Box 7031, Amagansett, NY Stay at this 3-star beach aparthotel in Amagansett. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ... 8.6/10 Excellent! (296 reviews) "The non ocean view rooms are fabulous. I’m sure the ocean side ones are great." Reviewed on Sep 30, 2025 [](https://expedia.ca/Amagansett-Hotels-Windward-Shores-Ocean-Resort.h4207136.Hotel-Information) [See all properties in Southold](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=183719&sort=VACATION_RENTAL) 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. ## Check Southold hotel availability [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183719&startDate=2025-10-07&endDate=2025-10-08) [Tonight](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183719&startDate=2025-10-07&endDate=2025-10-08) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183719&startDate=2025-10-07&endDate=2025-10-08) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183719&startDate=2025-10-07&endDate=2025-10-08)[Oct 7 - Oct 8](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183719&startDate=2025-10-07&endDate=2025-10-08) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183719&startDate=2025-10-08&endDate=2025-10-09) [Tomorrow night](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183719&startDate=2025-10-08&endDate=2025-10-09) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183719&startDate=2025-10-08&endDate=2025-10-09) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183719&startDate=2025-10-08&endDate=2025-10-09)[Oct 8 - Oct 9](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183719&startDate=2025-10-08&endDate=2025-10-09) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183719&startDate=10%2F10%2F2025&endDate=12%2F10%2F2025) [This weekend](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183719&startDate=10%2F10%2F2025&endDate=12%2F10%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183719&startDate=10%2F10%2F2025&endDate=12%2F10%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183719&startDate=10%2F10%2F2025&endDate=12%2F10%2F2025)[Oct 10 - Oct 12](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183719&startDate=10%2F10%2F2025&endDate=12%2F10%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183719&startDate=17%2F10%2F2025&endDate=19%2F10%2F2025) [Next weekend](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183719&startDate=17%2F10%2F2025&endDate=19%2F10%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183719&startDate=17%2F10%2F2025&endDate=19%2F10%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183719&startDate=17%2F10%2F2025&endDate=19%2F10%2F2025)[Oct 17 - Oct 19](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=183719&startDate=17%2F10%2F2025&endDate=19%2F10%2F2025) ### Popular places to visit ![Sparkling Pointe](https://mediaim.expedia.com/destination/2/3f9e84132c7cf86c180b2490717bed52.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Sparkling Pointe You can enjoy a tasting or tour at Sparkling Pointe during your travels to Southold. Discover the sunsets and wineries in this family-friendly area. [](https://expedia.ca/Sparkling-Pointe-Southold.d6327589.Vacation-Attraction) #### Sannino's Bella Vita Vineyard You can enjoy a tasting or tour at Sannino's Bella Vita Vineyard during your travels to Southold. Wander the beaches or discover the sunsets in this family-friendly area. [](https://expedia.ca/Sanninos-Bella-Vita-Vineyard-Southold.d6327435.Vacation-Attraction) #### Croteaux Vineyards You can enjoy a tasting or tour at Croteaux Vineyards during your travels to Southold. Wander the beautiful beaches in this family-friendly area. [](https://expedia.ca/Croteaux-Vineyards-Southold.d6326852.Vacation-Attraction) #### Osprey's Dominion You can enjoy a tasting or tour at Osprey's Dominion during your travels to Southold. Wander the beautiful beaches in this family-friendly area. [](https://expedia.ca/Ospreys-Dominion-Southold.d6326243.Vacation-Attraction) #### Corey Creek Winery You can enjoy a tasting or tour at Corey Creek Winery during your travels to Southold. Wander the beautiful beaches in this family-friendly area. [](https://expedia.ca/Corey-Creek-Winery-Southold.d6326844.Vacation-Attraction) #### Horton Point Park Explore the great outdoors at Horton Point Park, a lovely green space in Southold. Wander the beaches or discover the sunsets in this family-friendly area. [](https://expedia.ca/Horton-Point-Park-Southold.d6064489.Vacation-Attraction) ### Things to do ![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 CA $203 per adult [](https://expedia.ca/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 CA $192 per adult [](https://expedia.ca/things-to-do/from-mattituck-north-fork-area-bike-tour-with-food-tasting.a48343602.activity-details) [See all activities in Southold](https://expedia.ca/Things-To-Do-In-Southold.d183719.Travel-Guide-Activities) ## Cities near Southold ![Photo by tom owens](https://mediaim.expedia.com/destination/2/57db4dbbb841fe5852df8ed4b2f64ec5.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Shelter Island [](https://expedia.ca/Shelter-Island.dx157359) ![Photo by Nina Dinoff](https://mediaim.expedia.com/destination/2/9a9f855657c0f02d64549df7b59e54eb.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Greenport West [](https://expedia.ca/Greenport-West.dx553248635975876381) - Cities near Southold - Places of interest [Shelter Island](https://expedia.ca/Shelter-Island.dx157359)[Greenport West](https://expedia.ca/Greenport-West.dx553248635975876381) - [Cooper's Beach](https://expedia.ca/Coopers-Beach-Southampton.d6326842.Vacation-Attraction) - [East Hampton Main Beach](https://expedia.ca/East-Hampton-Main-Beach-East-Hampton.d6326946.Vacation-Attraction) - [Essex Steam Train](https://expedia.ca/Essex-Steam-Train-Essex.d6171206.Vacation-Attraction) - [Wolffer Estates Vineyard](https://expedia.ca/Wolffer-Estates-Vineyard-Sagaponack.d6064497.Vacation-Attraction) - [Hither Hills State Park](https://expedia.ca/Hither-Hills-State-Park-Montauk.d553248621532665771.Vacation-Attraction) - [Tanger Outlet Center](https://expedia.ca/Tanger-Outlet-Center-Riverhead.d6224628.Vacation-Attraction) - [Kontokosta Winery](https://expedia.ca/Kontokosta-Winery-Greenport.d6326928.Vacation-Attraction) - [Pindar Vineyards](https://expedia.ca/Pindar-Vineyards-Peconic.d6326965.Vacation-Attraction) ![](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 ![QR code to download the app](data:image/png;base64,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)