Title: Top Southold Cabin Rentals | 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) # Find Cabins in Southold for Rent from CA $971 - ![](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 In two weeks [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Southold Cabin Rentals ![Exterior](https://images.trvl-media.com/lodging/106000000/105190000/105183900/105183859/7dda8a8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105190000/105183900/105183859/efa99c71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105190000/105183900/105183859/d7bdc93b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105190000/105183900/105183859/c6f6bbf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature Killingworth 10/10 Exceptional (51) "Amazing property, we loved everything about it, highly recommended, will stay again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rick CA $505 CA $971 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Killingworth-Hotels-Cozy-Cabin-In-The-Woods-Situated-On-6-Private-Acres-Surrounded-By-Nature.h105183859.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=2025-11-28&endDate=2025-11-29®ionId=183719&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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-Cabins.d183719-aaCabins.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouthold-Cabins.d183719-aaCabins.Travel-Guide-Accommodation) ## Top Southold Hotel Reviews ![Sag Harbor Inn](//images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/14a9b9bf_y.jpg) ### Sag Harbor Inn 10/10 Excellent "Great room, with a great view" [](https://expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.Hotel-Information) ![The Harbor Front Inn](//images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca_y.jpg) ### The Harbor Front Inn 10/10 Excellent "Awesome stay!!! Great Location " [](https://expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![The Bentley Hotel Southampton](//images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98_y.jpg) ### The Bentley Hotel Southampton 10/10 Excellent "From the front desk receptionist to checking out, everything was perfect. " [](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![The Shoals Suites and Slips](//images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/968755d8_y.jpg) ### The Shoals Suites and Slips 10/10 Excellent "This was a stunning place to stay in all respects. The large room was wonderrful. Thank you! " [](https://expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) ![The Sagaponack](//images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/d64f35e8_y.jpg) ### The Sagaponack 10/10 Excellent "Great place, wonderful attention to details. Friendly and helpful staff. Comfortable bed. Will be back!" [](https://expedia.ca/Wainscott-Hotels-The-Wainscott-Inn.h81143153.Hotel-Information) ![Saybrook Point Resort & Marina](//images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108_y.jpg) ### Saybrook Point Resort & Marina 10/10 Excellent "Hospitality at its finest! Bed here was beyond comfortable❤️" [](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information) ![Sound View Greenport](//images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "Staff was amazing , room clean view phenomenal " [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Madison Beach Hotel](//images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/18df186b_y.jpg) ### Madison Beach Hotel 10/10 Excellent "I can't say enough about our stay at the Madison Beach Hotel. From the moment we arrived we were treated very well. The view from our room was spectacular. It was so peacful sitting on the balconey listening to the waves and the entire property is beautiful. Spent some time in the shops and restaurants downtown. Dinner at the Wharf restaurant was very nice. Highly recommend breakfast at Christy's next door and we had a great lunch/drinks at Aqua in nearby Clinton. We will definitely be booking another stay at this hotel soon." [](https://expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.Hotel-Information) ![The Preston House & Hotel](//images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/1f765cec_y.jpg) ### The Preston House & Hotel 10/10 Excellent "Was greeted by Christian, it was a smooth, friendly and easy check in. Hotel is super clean, super modern and in a great location. Breakfast was good. Yogurt, really good croissants, coffee, pastries, cereal, very nice selection and also fresh fruit and juices. Bed was comfortable and i wish i stayed longer to check out the bar and restaurant. Easy breezy check out with another great staff member that i didnt catch her name. Looking forward to booking this place again. " [](https://expedia.ca/Riverhead-Hotels-The-Preston-House-Hotel.h21825843.Hotel-Information) ## Find out more about Southold ## Southold Cabin Rentals information | Number of reviews | 51 | | --- | --- | | Accommodation | 4 Cabin Rentals | | Lowest Price | CA $971 | | Highest Price | CA $971 | ## Frequently asked questions ### What are the best cabins near Southold? > Ranging from small and rustic to large and luxurious, you have 39 cabins to choose from in and around Southold. Top options include [Rustic Lakeside Cabin At White Gate Farm](https://www.expedia.ca/Mystic-New-London-Hotels-Rustic-Lakeside-Cabin-At-White-Gate-Farm.h54202033.Hotel-Information) and [Cabin - Treehouse - Countryside - Farm Animals](https://www.expedia.ca/Willington-Hotels-Treehouse-On-Animal-Farm-W-Bonfire-Gazebo.h61486755.Hotel-Information). ### Are there cheap cabins near Southold? > For a memorable vacation in nature, look no further than our cheap cabins near Southold. Wake every morning to the sounds of wildlife and birds from one of our cozy cabin rentals priced from CA $971 to CA $971 per night.These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply. ### What are the best mountain cabins near Southold? > If you're yearning for crisp air and stunning views, escape the city and stay in a Southold mountain cabin. Unplug from it all at [Rustic Lakeside Cabin At White Gate Farm](https://www.expedia.ca/Mystic-New-London-Hotels-Rustic-Lakeside-Cabin-At-White-Gate-Farm.h54202033.Hotel-Information). This lofty stay has all the ingredients for an idyllic escape, including a microwave oven and a kitchen. Or, enjoy a taste of the mountain lifestyle at [Mohegan Cabin Estate](https://www.expedia.ca/Montville-Hotels-Mohegan-Cabin-Estate.h92899531.Hotel-Information). It comes with winery tours, a microwave oven and more. ### What are the best pet-friendly cabins near Southold? > You won't have to organize a pet sitter if you're on your way to Southold. Pooch-friendly properties like [Rustic Lakeside Cabin At White Gate Farm](https://www.expedia.ca/Mystic-New-London-Hotels-Rustic-Lakeside-Cabin-At-White-Gate-Farm.h54202033.Hotel-Information) will make you and your four-legged pal feel welcome and cared for. Children's activities and on-site watersports are among the conveniences here. [Remote Long Island Lakefront Cabin W](https://www.expedia.ca/Middle-Island-Hotels-Secluded-Long-Island-Lakefront-Cabin-Wdeckgrill.h42615443.Hotel-Information) is also a paw-fect option for pets and their owners. A deck and a queen bed are some of its amenities. ### What are the best cabins with pools near Southold? > Staying in a cabin rental with a pool adds another level of excitement to your vacation. If you're chasing one near Southold, [Cabin - Water Mill Wooded Escape](https://www.expedia.ca/Water-Mill-Hotels-Water-Mill-Wooded-Escape.h83758408.Hotel-Information) has useful amenities like a swimming pool and fitness facilities to make your poolside getaway even more memorable. [Spacious And New Deluxe Cabin In Family Campground In Northeastern Ct](https://www.expedia.ca/Ashford-Hotels-Spacious-And-New-Deluxe-Cabin-In-Family-Campground-In-Northeastern-CT.h83222046.Hotel-Information) is another top pick and features on-site watersports and a swimming pool. ### Can I find beach cabins near Southold? > Pack a few Hawaiian shirts and soak up the seaside vibes at [Rustic Lakeside Cabin At White Gate Farm](https://www.expedia.ca/Mystic-New-London-Hotels-Rustic-Lakeside-Cabin-At-White-Gate-Farm.h54202033.Hotel-Information). This Southold beach cabin has amenities including on-site watersports and beach sun loungers. [Lagoon Lodge: North Fork, Charming 3br](https://www.expedia.ca/East-Marion-Hotels-Lagoon-Lodge-North-Fork-Charming-3Br-Waterfront-W-Boat-Doc-Walk-On-Beach.h76596794.Hotel-Information) also promises a sun-soaked escape. Featuring clothes washing facilities and children's activities, it's where many beach vacation memories are made. ### What are the best weekend cabin rentals in Southold? > Nothing beats a weekend cabin getaway after a draining week at work. Swap your cramped office for two or three days in the great outdoors at [Rustic Lakeside Cabin At White Gate Farm](https://www.expedia.ca/Mystic-New-London-Hotels-Rustic-Lakeside-Cabin-At-White-Gate-Farm.h54202033.Hotel-Information). On-site watersports and a private beach are some handy amenities it offers. Alternatively, clear away some cobwebs at [Cabin - Treehouse - Countryside - Farm Animals](https://www.expedia.ca/Willington-Hotels-Treehouse-On-Animal-Farm-W-Bonfire-Gazebo.h61486755.Hotel-Information). Settle in here and enjoy access to a patio and a fireplace. ### What are the best cabin prices near Southold? > With prices starting from just CA $971 a night for a cabin rental near Southold, there's no reason to bother with that impossible-to-pitch tent. ### Can I find log cabins in Southold? > If you find yourself pining for a less hectic pace of life, you'll discover it at one of our log cabins in Southold. For example, [The Retreat Log Cabin](https://www.expedia.ca/Charlestown-Hotels-The-Retreat-Log-Cabin.h83249844.Hotel-Information). Spend your days here going boating and parasailing and then return home to its rustic charms. You can also hit the brakes at [Log Cabin, 5 Min To Casino With Pond](https://www.expedia.ca/Preston-Hotels-Log-Cabin.h87731734.Hotel-Information). When you're ready to explore beyond your cozy digs, snowboarding and canoeing opportunities are nearby. ### What are the highest-rated cabins in Southold? > There are some rentals that are just about perfect. [Remote Long Island Lakefront Cabin W](https://www.expedia.ca/Middle-Island-Hotels-Secluded-Long-Island-Lakefront-Cabin-Wdeckgrill.h42615443.Hotel-Information) is one of them. With an impressive rating, it comes with useful amenities such as a patio and a fireplace. Another terrific option is [Cabin - Treehouse - Countryside - Farm Animals](https://www.expedia.ca/Willington-Hotels-Treehouse-On-Animal-Farm-W-Bonfire-Gazebo.h61486755.Hotel-Information). A patio and a fireplace are a few of the conveniences here. ### Why should I book a cabin in Southold? > Affordability, comfort, rustic charm — there are lots of reasons to book a Southold cabin. Escape the loud and lively city and wake up to the sounds of birds and wildlife. There's ample adventure within striking distance too. 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[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) - [Kontokosta Winery](https://www.expedia.ca/Kontokosta-Winery-Greenport.d6326928.Vacation-Attraction) - [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) - 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