Title: Book the Best Southold Hotels with FREE PARKING in 2025 | 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 Hotels with Free Parking in Southold, NY from CA $115 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 Hotels with Free Parking Tonight [Oct 5 - Oct 6](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-10-05&endDate=2025-10-06&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 6 - Oct 7](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-10-06&endDate=2025-10-07&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Southold Hotels with Free Parking ![Property grounds](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/9ab5b9c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/7bb1af0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/f2520f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Double Beds](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/d45c604d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Clinton Motel Clinton 8.6/10 Excellent (279) "Great staff and clean rooms" CA $109 CA $125 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/afdef753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/72f65e39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/31bd2f7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pier Blue Inn Old Saybrook - Essex Saybrook Manor 8.0/10 Very good (1004) "Very friendly and helpful staff." CA $112 CA $129 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/08241fb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/bc78fd2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/735ceae9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/tub, hair dryer, towels, soap](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/afd83ae8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spark by Hilton Guilford Guilford 8.4/10 Very good (36) "Good clean property with great staff " CA $156 CA $179 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/4000000/3010000/3004600/3004551/8ac8989f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/4000000/3010000/3004600/3004551/374b57af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3010000/3004600/3004551/7e8d204d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3010000/3004600/3004551/ad4e87dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Liberty Inn Old Saybrook 7.4/10 Good (631) "Well located for getting to the places we wanted to be. This is an older property, but well taken care of and service was very good. I wouldn’t hesitate to stay here again. " CA $103 CA $119 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Old-Saybrook-Hotels-Liberty-Inn.h3004551.Hotel-Information) ![Indoor pool, open 9:00 AM to 9:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, Multiple Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/0b15e4f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/511d84f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/8ffa2c0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Old Saybrook - Westbrook Old Saybrook 7.6/10 Good (1003) "We have stayed there before so have been pleased with it." CA $130 CA $150 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/3c3df51f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/a7102e12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/c3d8e2ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/e78d099b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Greenporter Hotel Greenport 9.2/10 Wonderful (259) "Staff was amazing and this hotel is in the perfect location " CA $184 CA $211 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Greenport-Hotels-Greenporter-Hotel.h90308554.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/ae918eba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sport court](https://images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/20fb5209.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/fc8f49f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/7454864c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean Vista Resort Amagansett 9.0/10 Wonderful (195) "Lovely short stay! Right on the beautiful beach. Staff were so welcoming and even quickly sent me something I accidentally left behind in the room. Absolutely plan to be back!" CA $187 CA $214 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Amagansett-Hotels-Ocean-Vista-Resort.h9388116.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/db00678f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/39934cf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/b026cb5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/f4e648ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Econo Lodge Inn & Suites Old Saybrook Westbrook Old Saybrook 7.2/10 Good (456) "the so-called breakfast was absolute minimum only thing available was make your own waffle" CA $100 CA $115 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Old-Saybrook-Hotels-Econo-Lodge-Inn-Suites-Old-Saybrook-Westbrook.h1177328.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/d12dc016.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/47245b49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/613daeae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mini-fridge, microwave, coffee/tea maker, toaster oven](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/496822b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Niantic Inn Niantic 9.0/10 Wonderful (110) "Nice place and town " CA $189 CA $218 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Niantic-Hotels-The-Niantic-Inn.h15001889.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/25000000/24400000/24391700/24391657/4bc04364.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pillowtop beds, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/25000000/24400000/24391700/24391657/f0b6b7c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/25000000/24400000/24391700/24391657/a73c08b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/25000000/24400000/24391700/24391657/fa5bb1dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Carole's Place B & B East Quogue 9.8/10 Exceptional (59) "Small B&B with a charming old school vibe. Second time we’ve stayed there and we will return." CA $209 CA $239 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/East-Quogue-Hotels-Caroles-Place-B-B.h24391657.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=2025-10-19&endDate=2025-10-20®ionId=183719&adults=2&amenities=FREE_PARKING&sort=RECOMMENDED&openPlayBack=true) ## Top Southold Hotel Reviews ![Water's Edge Resort & Spa](//images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg) ### Water's Edge Resort & Spa 10/10 Excellent "Beautiful grounds, well maintained property. Our room was clean and comfortable. Definitely want to come back and extend our stay with family and friends. It’s a beautiful escape on the East Coast " [](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information) ![Spark by Hilton Guilford](//images.trvl-media.com/lodging/1000000/990000/983200/983128/08241fb2_y.jpg) ### Spark by Hilton Guilford 10/10 Excellent "Wow this has been an eye opener, what a fabulous hotel . It sparked my joy " [](https://expedia.ca/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.Hotel-Information) ![Pier Blue Inn Old Saybrook - Essex](//images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg) ### Pier Blue Inn Old Saybrook - Essex 10/10 Excellent "Only issue....the refrigerator makes an annoying sound which is amlpified wearing hearing aids" [](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![Greenview Inn Riverhead](//images.trvl-media.com/lodging/2000000/1380000/1374000/1373980/d1b868c8_y.jpg) ### Greenview Inn Riverhead 10/10 Excellent "All new decor . Very clean . Helpful staff" [](https://expedia.ca/Riverhead-Hotels-Greenview-Inn-Riverhead.h1373980.Hotel-Information) ![Quality Inn Old Saybrook - Westbrook](//images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg) ### Quality Inn Old Saybrook - Westbrook 10/10 Excellent "Liked having and using pool. didn't realize there would be a swimming lesson going on at same time. As this was a quick stop over on our way to Bar Harbor, it fit our needs. Since the room was on the street side it was a bit noisy even with fan running all the time. The room was clean and comfortable and we enjoyed the breakfast which was included. " [](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ![Zey Hotel](//images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978_y.jpg) ### Zey Hotel 10/10 Excellent "Clean and quiet right on a main street with plenty of shopping and dining. Very close to the vineyards. Great stay." [](https://expedia.ca/Greenport-Hotels-The-Gallery-Hotel.h15622089.Hotel-Information) ![Hotel Indigo East End by IHG](//images.trvl-media.com/lodging/4000000/3480000/3475700/3475618/75016698_y.jpg) ### Hotel Indigo East End by IHG 10/10 Excellent "Best place ever!!! Love it 💕 Food and Staff was amazing " [](https://expedia.ca/Riverhead-Hotels-Hotel-Indigo-East-End.h3475618.Hotel-Information) ![Ocean Vista Resort](//images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/ae918eba_y.jpg) ### Ocean Vista Resort 10/10 Excellent "Lovely short stay! Right on the beautiful beach. Staff were so welcoming and even quickly sent me something I accidentally left behind in the room. Absolutely plan to be back!" [](https://expedia.ca/Amagansett-Hotels-Ocean-Vista-Resort.h9388116.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 "Loved everything about this property. Location, Staff, Amenities. Decor and furniture beautiful. 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[Cheap Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Cheap-Hotels.0-0-d110728-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Greenport](https://www.expedia.ca/Greenport-Hotels-Couples-Resorts-Hotels.0-0-d110728-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Lake Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Lake-Hotels.0-0-d110728-tLakeHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Luxury-Hotel.0-0-d110728-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Oceanfront-Hotels.0-0-d110728-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Shopping Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Shopping-Hotel.0-0-d110728-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Spa-Hotel.0-0-d110728-tSpaHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Greenport](https://www.expedia.ca/Greenport-Hotels-Waterpark-Hotels.0-0-d110728-tWaterparkHotels.Travel-Guide-Filter-Hotels) - 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