Title: Southold B&B: Find the Best Bed and Breakfast from CA $239 | 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 $239 ![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 prices for these dates Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [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 months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=183719&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Southold B&B ![Property grounds](https://images.trvl-media.com/lodging/25000000/24400000/24391700/24391657/4bc04364.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) ![Smart TV](https://images.trvl-media.com/lodging/25000000/24400000/24391700/24391657/fa5bb1dc.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) ### 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 8 - Oct 9 [](https://www.expedia.ca/East-Quogue-Hotels-Caroles-Place-B-B.h24391657.Hotel-Information) ![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) ![Porch](https://images.trvl-media.com/lodging/2000000/1480000/1480000/1479959/7506bfd3.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) ### The Captain Stannard Westbrook Center 9.6/10 Exceptional (249) "Everything was fantastic, will stay again!" CA $299 CA $332 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Westbrook-Hotels-Captain-Stannard-BB-Country-Inn.h1479959.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) ![Exterior detail](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/9a89f493.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) ![Property entrance](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/ce84672e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Sagaponack Wainscott 8.8/10 Excellent (188) "Great stay!" CA $223 CA $311 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Wainscott-Hotels-The-Wainscott-Inn.h81143153.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) ![Garden](https://images.trvl-media.com/lodging/32000000/31010000/31007600/31007589/9d3a1088.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) ### East Hampton Art House Bed & Breakfast Clearwater Beach 9.6/10 Exceptional (64) "Roz and Michael built a beautiful paradise that they enjoy sharing with you. Everything is amazing. " CA $530 CA $605 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/East-Hampton-Hotels-East-Hampton-Art-House-Bed-Breakfast.h31007589.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) ![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) ![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) ![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) ### Westbrook Inn B&B Westbrook Center 9.8/10 Exceptional (170) "Charming, beautiful inn; excellent food and service." CA $297 CA $330 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Old-Saybrook-Hotels-Westbrook-Inn-Bed-And-Breakfast.h35596310.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 | Terrace/patio](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/1f2aee03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Graybarn Cottage | Room amenity](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/1d639007.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mill House Inn North Main Street Historic District 9.0/10 Wonderful (70) "Great experience at a wonderful property!" CA $453 CA $570 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/East-Hampton-Hotels-Mill-House-Inn.h2861838.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) ![Garden](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/98031383.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) ### James Pharmacy Bed & Breakfast Old Saybrook Center 9.2/10 Wonderful (19) "My husband and I stayed here for a quick weekend getaway and loved our experience! The location was perfect - located near restaurants, shops, and the beach - and the room was clean and charming. We will definitely be back!" CA $421 CA $468 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Old-Saybrook-Hotels-James-Pharmacy-Bed-Breakfast.h78191036.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) ![Exterior detail](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/553f589d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/36000000/35380000/35373800/35373712/e5f6999f.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) ### The Huntting Inn East Hampton 9.0/10 Wonderful (103) "What a wonderful place to stay! The room was beautiful. The bed was comfortable and the staff were welcoming and helpful. We loved how close it was to town. We also enjoyed the breakfast every morning. The Palm restaurant downstairs was nice to have on property and the food was great. We will definitely stay again!" CA $533 CA $623 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/East-Hampton-Hotels-The-Huntting-Inn.h35373712.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/32000000/31960000/31958900/31958886/90437a31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/32000000/31960000/31958900/31958886/5ee4b9df.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!" CA $388 CA $431 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Old-Saybrook-Hotels-The-Homestead.h31958886.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) ![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) ![Interior detail](https://images.trvl-media.com/lodging/37000000/36880000/36879900/36879849/565c8d39.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) ### Harpoon House Southampton 8.4/10 Very good (143) "Very cute location- rooms are very spacious. We were able to walk into town. Would definitely stay again. " CA $445 CA $509 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Southampton-Hotels-Harpoon-House.h36879849.Hotel-Information) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/19000000/18640000/18632700/18632615/58da24df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/19000000/18640000/18632700/18632615/affe9b7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18640000/18632700/18632615/7af2d0a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18640000/18632700/18632615/42ef7c54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### West Neck Guesthouse Shelter Island Heights 8.0/10 Very good (37) "Great property! Close to beach and super clean. " CA $499 CA $570 total includes taxes & fees Oct 17 - Oct 18 [](https://www.expedia.ca/Shelter-Island-Heights-Hotels-West-Neck-Guesthouse.h18632615.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) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83270000/83267900/83267867/ddb44815.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83270000/83267900/83267867/bce72168.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 $1,121 total includes taxes & fees Oct 8 - Oct 9 [](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=2025-10-21&endDate=2025-10-22®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 "Great place, beautiful views! I’ll be back." [](https://expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) ![Greenview Inn Riverhead](//images.trvl-media.com/lodging/2000000/1380000/1374000/1373980/d1b868c8_y.jpg) ### Greenview Inn Riverhead 10/10 Excellent "I was really impressed with the modern, clean room. I loved the sliding barn door..clean, white bedding & refillable soap & shampoo & conditioner. No more little plastic bottles that never hold enough to even wash one person’s hair. I also lined the separate reading lights. The gentleman checking us in was pleasant and it took a very short time. I would definitely consider another visit next time I am visiting the North Fork of Long Island." [](https://expedia.ca/Riverhead-Hotels-Greenview-Inn-Riverhead.h1373980.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 "Clean room!!" [](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.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 "Relaxing wonderful staff!" [](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.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 "Great experience, loved the bartender and happy hour. Very friendly staff ." [](https://expedia.ca/Riverhead-Hotels-Hotel-Indigo-East-End.h3475618.Hotel-Information) ![Greenporter Hotel](//images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/3c3df51f_y.jpg) ### Greenporter Hotel 10/10 Excellent "Great stay! Lovely people! Great area!" [](https://expedia.ca/Greenport-Hotels-Greenporter-Hotel.h90308554.Hotel-Information) ![Sound View Greenport](//images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "Nice views on sunset" [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![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) ![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 "We were there 1 night, so i didnt notice shops. But there was a good restaurant across the road." [](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 | 1,178 | | --- | --- | | Accommodation | 38 B&B | | Lowest Price | CA $239 | | Highest Price | CA $1,121 | ## 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. [East Hampton Art House Bed & Breakfast](https://www.expedia.ca/East-Hampton-Hotels-East-Hampton-Art-House-Bed-Breakfast.h31007589.Hotel-Information): 2 rooms. Situated 13.9 mi (22.3 km) from the heart of Southold. Enjoy the free full breakfast and fitness center. [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. [James Pharmacy Bed & Breakfast](https://www.expedia.ca/Old-Saybrook-Hotels-James-Pharmacy-Bed-Breakfast.h78191036.Hotel-Information): 3 rooms. Located 15.5 mi (25 km) from the core of Southold. Enjoy the local cuisine breakfast and designer toiletries. ### 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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