Title: Southold B&B: Find the Best Bed and Breakfast from CA $321 | 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 a Bed and Breakfast in Southold from CA $321 ![](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 [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Southold B&B ![IPod dock, MP3 dock](https://images.trvl-media.com/lodging/2000000/1480000/1480000/1479959/497076d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/2000000/1480000/1480000/1479959/5ebf0e7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1480000/1480000/1479959/ab015163.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Bedroom, Private Bathroom](https://images.trvl-media.com/lodging/2000000/1480000/1480000/1479959/bce7c7c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Captain Stannard Westbrook Center 9.6/10 Exceptional (253) "Clean, friendly and delicious continental breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Miriam [](https://www.expedia.ca/Westbrook-Hotels-Captain-Stannard-BB-Country-Inn.h1479959.Hotel-Information) ![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) ![Property grounds](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/f6e6bd4f.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 | Terrace/patio](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/1f2aee03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mill House Inn North Main Street Historic District 9.0/10 Wonderful (70) "Delightful property and even more delightful staff. love staying here! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brittany CA $420 CA $527 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/East-Hampton-Hotels-Mill-House-Inn.h2861838.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/d64f35e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/d13a2c2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/ce84672e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Suite](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/3be2d342.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Sagaponack Wainscott 8.8/10 Excellent (196) "The room was spotless and had everything that you would need. Would stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marjorie CA $232 CA $321 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Wainscott-Hotels-The-Wainscott-Inn.h81143153.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/46915263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/22d95002.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/f2c9a8ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Clinton Room](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/6c9c9c01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Westbrook Inn B&B Westbrook Center 9.8/10 Exceptional (173) "Beautiful place and wonderful staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebecca CA $301 CA $335 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Old-Saybrook-Hotels-Westbrook-Inn-Bed-And-Breakfast.h35596310.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) ![Front of property](https://images.trvl-media.com/lodging/25000000/24400000/24391700/24391657/58d33334.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Carole's Place B & B East Quogue 9.8/10 Exceptional (60) "Very clean and quiet, super comfortable bed, good central location to get around on Long Island, and an great host." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael [](https://www.expedia.ca/East-Quogue-Hotels-Caroles-Place-B-B.h24391657.Hotel-Information) ![Miss Anna James Room](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/w848h631x48y3-ad11e9c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/e61ec435.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/f09f38b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/98031383.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### James Pharmacy Bed & Breakfast Old Saybrook Center 9.2/10 Wonderful (20) "Beautiful property in a great location, convenient to everything.Our room was clean and comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ray CA $421 CA $468 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Old-Saybrook-Hotels-James-Pharmacy-Bed-Breakfast.h78191036.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/4db6535f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/6809b461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/d9c11af0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Master Guest Room](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/90421aa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### East Hampton Art House Bed & Breakfast Clearwater Beach 9.6/10 Exceptional (65) "The hosts were really nice and the breakfast is excellent!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) IVAN CA $530 CA $605 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/East-Hampton-Hotels-East-Hampton-Art-House-Bed-Breakfast.h31007589.Hotel-Information) ![Room, 1 King Bed, Patio, Ground Floor (7)](https://images.trvl-media.com/lodging/32000000/31960000/31958900/31958886/c76f25a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/32000000/31960000/31958900/31958886/f87cac33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![36-inch Smart TV with cable channels, TV, Netflix](https://images.trvl-media.com/lodging/32000000/31960000/31958900/31958886/6b4787fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Traditional House | Living area](https://images.trvl-media.com/lodging/32000000/31960000/31958900/31958886/e8c6bce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Homestead Madison Center 10/10 Exceptional (87) "This is our 2nd year staying at the Homestead B & B. We absolutely love it here! Great food, amenities galore, and just an awesome getaway!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cynthia CA $375 CA $417 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Old-Saybrook-Hotels-The-Homestead.h31958886.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/98e9a1b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/398ec458.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/553f589d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free continental breakfast on weekends](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/062f5fd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Huntting Inn Egypt Lane Historic District 9.0/10 Wonderful (104) "Staff and management was very welcoming!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sanailer CA $533 CA $623 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/East-Hampton-Hotels-The-Huntting-Inn.h35373712.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/113000000/112910000/112907700/112907611/ea3c7561.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112910000/112907700/112907611/84e7ebf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Traditional Cottage, 2 Bedrooms, Lake View](https://images.trvl-media.com/lodging/113000000/112910000/112907700/112907611/45454390.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Traditional Cottage, 2 Bedrooms, Lake View | Living area](https://images.trvl-media.com/lodging/113000000/112910000/112907700/112907611/6833ca01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Head of Pond House Water Mill 10/10 Exceptional (2) "Beautiful place with a very kind host. Highly recommend this place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michèle CA $734 CA $839 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Water-Mill-Hotels-Head-Of-Pond-House.h112907611.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/37000000/36880000/36879900/36879849/27aa2ee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Room, 1 King Bed](https://images.trvl-media.com/lodging/37000000/36880000/36879900/36879849/07ed4b21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Minibar, in-room safe, individually decorated, individually furnished](https://images.trvl-media.com/lodging/37000000/36880000/36879900/36879849/354f7655.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/37000000/36880000/36879900/36879849/802040b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harpoon House Southampton 8.4/10 Very good (146) "Very cute location- rooms are very spacious. We were able to walk into town. Would definitely stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karissa CA $455 CA $520 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Southampton-Hotels-Harpoon-House.h36879849.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83270000/83267900/83267867/9b41c5a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/84000000/83270000/83267900/83267867/0d06a5f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83270000/83267900/83267867/4fd6cfcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83270000/83267900/83267867/ddb44815.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Large Room w use of pool/tennis in Spacious home Sag Harbor CA $797 CA $1,150 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Sag-Harbor-Hotels-Large-Room-W-Use-Of-Pooltennis-In-Spacious-Home.h83267867.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=2025-11-14&endDate=2025-11-15®ionId=183719&adults=2&lodging=BED_AND_BREAKFAST&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-Bed-And-Breakfast.d183719-aaBedAndBreakfast.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouthold-Bed-And-Breakfast.d183719-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Southold Hotel Reviews ![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 "Everything was Amazing! " [](https://expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.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 "The staff was beyond helpful and nice, the rooms are huge and clean. Would definitely recommend " [](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.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 "I need an overnight stay with decent accomodations - this fit well inside my price range and comfort." [](https://expedia.ca/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.Hotel-Information) ![The Atlantic Hotel](//images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg) ### The Atlantic Hotel 10/10 Excellent "Perfect " [](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information) ![Sound View Greenport](//images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "Beautiful Long Island Sound and sunset views." [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Greenview Inn Riverhead](//images.trvl-media.com/lodging/2000000/1380000/1374000/1373980/d1b868c8_y.jpg) ### Greenview Inn Riverhead 10/10 Excellent "The place is a little bit outdated nature a little bit of uplift but other than that it's still the best deal on Long Island and especially around Riverhead. Well worth the $97 that they are charging, but every other place is $200 and not worth it." [](https://expedia.ca/Riverhead-Hotels-Greenview-Inn-Riverhead.h1373980.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 "Beautiful view and room. Staff friendly and accommodating. Excellent location. " [](https://expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Madison Beach Hotel](//images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/18df186b_y.jpg) ### Madison Beach Hotel 10/10 Excellent "Beautiful hotel ! Great waterviews, staff and restaurant food !" [](https://expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.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 "Everything was good, had a quiet happy stay." [](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ## Find out more about Southold ## Southold B&B information | Number of reviews | 1,168 | | --- | --- | | Accommodation | 38 B&B | | Lowest Price | CA $321 | | Highest Price | CA $1,150 | ## Frequently asked questions ### Searching for B&Bs in Southold? > If you're looking for something a little different than your standard hotel experience, a stay at a bed and breakfast could be a great option for your trip. If you'd like to spend some time by the water during your time in Southold, McCabe's Beach and Horton Lane Beach are worth a stop. ### How do you know if a B&B is the right choice for your stay? > With attentive service, opportunities to interact with the owner, and breakfast served on site, B&Bs provide a unique setting. ### What are the top B&Bs in Southold? > Here are some well-liked B&Bs in the area: [Vine & Sand](https://www.expedia.ca/Southold-Hotels-Vine-Sand.h96718085.Hotel-Information): 4 rooms. 1.3 mi (2.1 km) from the heart of Southold. Enjoy the free buffet breakfast and designer toiletries. [The Sagaponack](https://www.expedia.ca/Wainscott-Hotels-The-Wainscott-Inn.h81143153.Hotel-Information): 12 mi (19.3 km) from the downtown core. [Mill House Inn](https://www.expedia.ca/East-Hampton-Hotels-Mill-House-Inn.h2861838.Hotel-Information): 10 rooms. Situated 14.3 mi (23.1 km) from the heart of Southold. Enjoy the free cooked breakfast and designer toiletries. [Harpoon House](https://www.expedia.ca/Southampton-Hotels-Harpoon-House.h36879849.Hotel-Information): 9 rooms. 12.4 mi (19.9 km) from the heart of downtown. Enjoy the bars and unique décor. [The Captain Stannard](https://www.expedia.ca/Westbrook-Hotels-Captain-Stannard-BB-Country-Inn.h1479959.Hotel-Information): 11 rooms. Located 15.2 mi (24.4 km) from the core of Southold. Enjoy the private yard and unique décor. ### How many Bed & Breakfasts will I be able to find in Southold? > Expedia has 5 B&Bs for your stay in Southold. ### When should I book my B&B in Southold? > When you're dreaming of a escape to Southold, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually August and July with an average temp of 70°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Southold is 57 inches. ### What is there to do in Southold? > If you're looking for some activities to entertain you on your trip, consider visiting Sparkling Pointe and Croteaux Vineyards. You might put Osprey's Dominion and Sannino's Bella Vita Vineyard on your list if you want to see more of the area. ### How can I get to and around Southold? > Planning your excursions in and around Southold is easier with these transportation options. Fly into East Hampton, NY (HTO), which is located 11.8 mi (18.9 km) away from the heart of the city. You can also search for flights into Westhampton, NY (FOK-Francis S. Gabreski), which is 19 mi (30.6 km) away. 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