Title: Southold Guest Houses | 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) ![](https://mediaim.expedia.com/destination/1/2af9844708ff5148df98a90729e7edaf.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Guest Houses in Southold ![](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 prices for these dates Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Southold Guest Houses ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/5a24caee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/f1ad96fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/a79f88d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/7abafcfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New and Modern Bridgehampton Accommodations Bridgehampton 9.6/10 Exceptional (15) "Had a great stay here with a small group. Host was very accommodating and responsive. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alyssa M. CA $284 CA $654 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Bridgehampton-Hotels-New-And-Modern-Bridgehampton-Accommodations.h105953388.Hotel-Information) ![Apartment, 2 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/4e100a77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's activities](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/949a0d23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/6142ad8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/a37c2d73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton's Vacation Inn Hampton Bays 9.0/10 Wonderful (318) "A great Hampton location that's less than a thirty minutes drive from Coopers Beach and South Hampton main street." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maggie CA $177 CA $202 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Hampton-Bays-Hotels-Bowens-By-The-Bays.h10211593.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/51be5ca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/fdb9f048.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/d7311f73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/8cc5044d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### House on Chase Creek The Heights 9.4/10 Exceptional (77) " This was my husband and my first time visiting Shelter Island and I feel lucky that my stay was at the House of ChaseCreek. Bill was excellent in helping us navigate our stay on the Island which made for an enjoyable experience. The house was charming , very clean , and had easy access to the town restaurant s, and Ferry. Highly recommend ! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maureen CA $259 CA $296 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Shelter-Island-Heights-Hotels-House-On-Chase-Creek.h12610909.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-02&endDate=2025-11-03®ionId=183719&adults=2&lodging=GUEST_HOUSE&sort=RECOMMENDED&openPlayBack=true) ![](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%2FSouthold-Guest-Houses.d183719-aaGuestHouses.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouthold-Guest-Houses.d183719-aaGuestHouses.Travel-Guide-Accommodation) ## Top Southold Hotel Reviews ## Find out more about Southold ## Southold Guest Houses information | Number of reviews | | | --- | --- | | Accommodation | Guest Houses | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [3 Star Hotels in Greenport](https://www.expedia.ca/3Star-Greenport-Hotels.s30-0-d110728.Travel-Guide-Filter-Hotels) - 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