Title: 20 Best B&B in Winter Park, FL - Bed and Breakfast from $667 | Expedia.com [Winter Park Travel Guide](https://expedia.com/Winter-Park.dx7902)[Hotels in Winter Park](https://expedia.com/Winter-Park-Hotels.d7902.Travel-Guide-Hotels)[Vacation Rentals in Winter Park](https://expedia.com/Winter-Park-Vacation-Rentals.d7902.Travel-Guide-VacationRentals)[Flights to Winter Park](https://expedia.com/Cheap-Flights-To-Winter-Park.d7902.Travel-Guide-Flights)[Things to do in Winter Park](https://expedia.com/Things-To-Do-In-Winter-Park.d7902.Travel-Guide-Activities)[Car Rentals in Winter Park](https://expedia.com/Car-Rentals-In-Winter-Park.d7902.Car-Rental-Guide)[Winter Park Vacation Packages](https://expedia.com/Winter-Park.d7902.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/553248621532654339/aef9d03a-cd86-4dcc-8e9d-049aef598da5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/553248621532654339/aef9d03a-cd86-4dcc-8e9d-049aef598da5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates Next weekend [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-04-10&endDate=2026-04-12&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-04-17&endDate=2026-04-19&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-05-01&endDate=2026-05-03&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-05-29&endDate=2026-05-31&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winter Park bed & breakfast ![Design Room | Living area | 40-inch Smart TV with digital channels, TV](https://images.trvl-media.com/lodging/91000000/90220000/90211700/90211686/747b8634.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Highchair](https://images.trvl-media.com/lodging/91000000/90220000/90211700/90211686/218ee3ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Design Room | Living area | 40-inch Smart TV with digital channels, TV](https://images.trvl-media.com/lodging/91000000/90220000/90211700/90211686/12771d68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90220000/90211700/90211686/8addfbd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Tiny Cottage in The Springs [](https://www.expedia.com/Orlando-Hotels-The-Tiny-Cottage-In-The-Springs.h90211686.Hotel-Information) Altamonte Springs 9.8/10 Exceptional (26 reviews) "I really like this place, this is the second time I have booked here. I do consider it whenever I travel to the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anastasia $649 nightly $667 total Apr 6 - Apr 7 Total with taxes and fees [](https://www.expedia.com/Orlando-Hotels-The-Tiny-Cottage-In-The-Springs.h90211686.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113040000/113039700/113039630/03f5acec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/114000000/113040000/113039700/113039630/635d6269.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/114000000/113040000/113039700/113039630/93dfb53c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113040000/113039700/113039630/a9e3153a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oakland Manor House [](https://www.expedia.com/Winter-Garden-Hotels-Oakland-Manor-House.h113039630.Hotel-Information) Oakland $885 nightly $995 total Apr 1 - Apr 2 Total with taxes and fees [](https://www.expedia.com/Winter-Garden-Hotels-Oakland-Manor-House.h113039630.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.com/Hotel-Search?startDate=2026-04-14&endDate=2026-04-15®ionId=7902&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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinter-Park-Bed-And-Breakfast.d7902-aaBedAndBreakfast.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinter-Park-Bed-And-Breakfast.d7902-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Winter Park Hotel Reviews ![Universal's Cabana Bay Beach Resort](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/4c48bd3d_y.jpg) ### Universal's Cabana Bay Beach Resort 10/10 Excellent "Great" [](https://expedia.com/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information) ![Rosen Inn at Pointe Orlando](https://images.trvl-media.com/lodging/1000000/10000/8900/8892/8068a653_y.jpg) ### Rosen Inn at Pointe Orlando 10/10 Excellent "This was a amazing hotel and the view at the top is beautiful. My family had an absolute blast. Funspot was one of the places we went with the kids.. fun time. Looking forward to going back soon. " [](https://expedia.com/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.Hotel-Information) ![Westgate Lakes Resort & Spa Universal Studios Area](https://images.trvl-media.com/lodging/1000000/810000/805000/804984/ffaf091a_y.jpg) ### Westgate Lakes Resort & Spa Universal Studios Area 8/10 Good "clean rooms and lots of amenities" [](https://expedia.com/Orlando-Hotels-Westgate-Lakes-Resort-Spa-Universal-Studios-Area.h804984.Hotel-Information) ![Caribe Royale Orlando](https://images.trvl-media.com/lodging/1000000/50000/40900/40865/075cd42b_y.jpg) ### Caribe Royale Orlando 10/10 Excellent "Love this resort! My family has been coming for 10 years. Always enjoy the pool and music, took advantage of the bball court this time. Pool staff is always excellent, above and beyond. Thank you Rolando. " [](https://expedia.com/Orlando-Hotels-Caribe-Royale-Orlando.h40865.Hotel-Information) ![B&B Hotel Orlando International Drive Near Universal - Newly Renovated!](https://images.trvl-media.com/lodging/1000000/30000/26800/26703/ca31fce1_y.jpg) ### B&B Hotel Orlando International Drive Near Universal - Newly Renovated! 10/10 Excellent "Parking was great and secured " [](https://expedia.com/Orlando-Hotels-Floridian-Express-Extended-Stay-Hotel.h26703.Hotel-Information) ![Lake Buena Vista Resort Village & Spa](https://images.trvl-media.com/lodging/2000000/1360000/1350900/1350864/16b6b8e7_y.jpg) ### Lake Buena Vista Resort Village & Spa 6/10 Okay "Very old and outdated place to stay. Has good amenities but for the price I rather get something more up to date and upscale " [](https://expedia.com/Orlando-Hotels-Lake-Buena-Vista-Resort-Village-Spa.h1350864.Hotel-Information) ![Fairfield Inn & Suites Lake Buena Vista in Marriott Village](https://images.trvl-media.com/lodging/1000000/480000/470900/470892/w4000h2663x0y0-13fc5e39_y.jpg) ### Fairfield Inn & Suites Lake Buena Vista in Marriott Village 2/10 Terrible "I was “upgraded” to a different room than what I had booked because they were having computer problems. The “better” room was horrible. I am glad they didn’t charge me more for the so called upgrade but I would never book this hotel again. " [](https://expedia.com/Orlando-Hotels-Fairfield-Inn-Suites-Lake-Buena-Vista-In-Marriott-Village.h470892.Hotel-Information) ![Rosen Inn Lake Buena Vista](https://images.trvl-media.com/lodging/1000000/10000/1300/1264/2a9be677_y.jpg) ### Rosen Inn Lake Buena Vista 6/10 Okay "The carpet in the room was dirty - clean socks were dirty after a short while. Toe nail clippings on the bathroom floor and loose grout in the tiled floor. " [](https://expedia.com/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.Hotel-Information) ![Coco Key Hotel & Water Park Resort](https://images.trvl-media.com/lodging/1000000/10000/300/228/84c2249c_y.jpg) ### Coco Key Hotel & Water Park Resort 10/10 Excellent "The kids had plenty to do at the hotel. The pools were great and the staff was very friendly." [](https://expedia.com/Orlando-Hotels-CoCo-Key-Hotel-And-Water-Resort-Orlando.h228.Hotel-Information) ## Find out more about Winter Park ## Winter Park B&B information | Number of reviews | 26 | | ----------------- | ------ | | Accommodation | 18 B&B | | Lowest Price | $667 | | Highest Price | $995 | ## Frequently asked questions ### What is the nightly rate for a Bed and Breakfast in Winter Park? ### When is the best time to book a Bed & Breakfast in Winter Park? > February, in particular, stands out as the most popular month, offering a festive atmosphere with numerous events and plenty of fresh powder. During this time, you can enjoy not only skiing but also snowshoeing and snowmobiling, all while surrounded by the stunning Rocky Mountain scenery. The lively après-ski scene adds to the experience, making it an excellent choice for those looking to unwind after an active day. > > > For travelers seeking a more budget-friendly option, consider visiting in early May. During this shoulder season, you can enjoy the beauty of the mountains as the snow begins to melt and flowers start to bloom. It's a quieter time, great for exploring local trails and soaking in the serene landscapes without the crowds. ### What is the difference between a Winter Park Bed and Breakfast and a hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - [Orlando Hotels ](https://www.expedia.com/Orlando-Hotels.d178294.Travel-Guide-Hotels) - [Resorts in Orlando ](https://www.expedia.com/Orlando-Resorts.d178294-aaResorts.Travel-Guide-Accommodation) - [Cheap Hotels in Orlando ](https://www.expedia.com/Orlando-Hotels-Cheap-Hotels.0-0-d178294-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Free Airport Shuttle in Orlando ](https://www.expedia.com/Orlando-Hotels-Hotels-With-Free-Airport-Shuttle.0-0-d178294-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels) - [Hotels near Albin Polasek Museum and Sculpture Gardens ](https://www.expedia.com/Albin-Polasek-Museum-And-Sculpture-Gardens-Hotels.0-l6154778-0.Travel-Guide-Filter-Hotels) - [Hotels near Universal Studios Florida ](https://www.expedia.com/Universal-Studios-Florida-Hotels.0-l6049239-0.Travel-Guide-Filter-Hotels) - [All-Inclusive Resorts in Orlando ](https://www.expedia.com/Orlando-Hotels-All-Inclusive-Hotel.0-0-d178294-tAllinclusiveHotel.Travel-Guide-Filter-Hotels) - [Hotels near Winter Park Country Club ](https://www.expedia.com/Winter-Park-Country-Club-Hotels.0-l6239878-0.Travel-Guide-Filter-Hotels) - [Hotels near Copland Tennis Stadium ](https://www.expedia.com/Copland-Tennis-Stadium-Hotels.0-l553248621563220224-0.Travel-Guide-Filter-Hotels) - [Hotels near Rollins College ](https://www.expedia.com/Rollins-College-Hotels.0-l6154361-0.Travel-Guide-Filter-Hotels) - [Hotels near Morse Museum of American Art ](https://www.expedia.com/Morse-Museum-Of-American-Art-Hotels.0-l6154772-0.Travel-Guide-Filter-Hotels) - [Hotels near Winter Park Corner Shopping Center ](https://www.expedia.com/Winter-Park-Corner-Shopping-Center-Hotels.0-l553248621532654341-0.Travel-Guide-Filter-Hotels) - [Hotels near Casa Feliz Historic Home Museum ](https://www.expedia.com/Casa-Feliz-Historic-Home-Museum-Hotels.0-l6154784-0.Travel-Guide-Filter-Hotels) - [Hotels near Winter Park Station ](https://www.expedia.com/Winter-Park-Station-Hotels.d6176530.Travel-Guide-Hotels) - [Hotels near Barker Stadium ](https://www.expedia.com/Barker-Stadium-Hotels.0-l553248621563220225-0.Travel-Guide-Filter-Hotels) - [Hotels near Kraft Azalea Gardens ](https://www.expedia.com/Kraft-Azalea-Gardens-Hotels.0-l553248621532654339-0.Travel-Guide-Filter-Hotels) - [Hotels near Virginia S. 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[Morse Museum of American Art ](https://www.expedia.com/Morse-Museum-Of-American-Art-Orlando.d6154772.Vacation-Attraction) - [Casa Feliz Historic Home Museum ](https://www.expedia.com/Casa-Feliz-Historic-Home-Museum-Orlando.d6154784.Vacation-Attraction) - [Winter Park Corner Shopping Center ](https://www.expedia.com/Winter-Park-Corner-Shopping-Center-Orlando.d553248621532654341.Vacation-Attraction) - [Rollins College ](https://www.expedia.com/Rollins-College-Orlando.d6154361.Vacation-Attraction) - [Barker Stadium ](https://www.expedia.com/Barker-Stadium-Orlando.d553248621563220225.Vacation-Attraction) - [Virginia S. Nelson Rose Garden ](https://www.expedia.com/Virginia-S-Nelson-Rose-Garden-Orlando.d6239868.Vacation-Attraction) - [Winter Park History Museum ](https://www.expedia.com/Winter-Park-History-Museum-Orlando.d553248621532654329.Vacation-Attraction) - [Cahall Sandspur Field ](https://www.expedia.com/Cahall-Sandspur-Field-Orlando.d6239859.Vacation-Attraction) - [Alfond Swimming Pool ](https://www.expedia.com/Alfond-Swimming-Pool-Orlando.d553248621558036313.Vacation-Attraction) - [All Fired Up ](https://www.expedia.com/All-Fired-Up-Orlando.d553248621532654330.Vacation-Attraction) - [Lake Virginia ](https://www.expedia.com/Lake-Virginia-Orlando.d553248621532654331.Vacation-Attraction) - [Crealde School of Art ](https://www.expedia.com/Crealde-School-Of-Art-Orlando.d6239848.Vacation-Attraction) - [Hannibal Square Heritage Center ](https://www.expedia.com/Hannibal-Square-Heritage-Center-Orlando.d553248621532654328.Vacation-Attraction) - [Winter Park Playhouse ](https://www.expedia.com/Winter-Park-Playhouse-Orlando.d553248621561885914.Vacation-Attraction) - [Winter Park Tennis Center ](https://www.expedia.com/Winter-Park-Tennis-Center-Orlando.d636723274468732928.Vacation-Attraction) - [Lake Rose ](https://www.expedia.com/Lake-Rose-Orlando.d6360988.Vacation-Attraction) - [Winter Park Village ](https://www.expedia.com/Winter-Park-Village-Orlando.d6239900.Vacation-Attraction) - [Howell Branch Preserve Pavilion ](https://www.expedia.com/Howell-Branch-Preserve-Pavilion-Orlando.d553248621532654340.Vacation-Attraction) - [Mead Garden ](https://www.expedia.com/Mead-Garden-Orlando.d6239861.Vacation-Attraction) - [Hollie Anna Shopping Center ](https://www.expedia.com/Hollie-Anna-Shopping-Center-Orlando.d553248621563220220.Vacation-Attraction) - [Lake Maitland Terrace Marina ](https://www.expedia.com/Lake-Maitland-Terrace-Marina-Orlando.d553248621563220228.Vacation-Attraction) - [Enzian Theater ](https://www.expedia.com/Enzian-Theater-Orlando.d6154880.Vacation-Attraction) - [Winter Pines Golf Club ](https://www.expedia.com/Winter-Pines-Golf-Club-Orlando.d6239892.Vacation-Attraction) - [Lee Road Shopping Center ](https://www.expedia.com/Lee-Road-Shopping-Center-Fairview-Shores.d553248621563220222.Vacation-Attraction) - [Visit Orwin Manor ](https://www.expedia.com/Orlando-Orwin-Manor.dx553248635976471367) - [Lake Lily Park ](https://www.expedia.com/Lake-Lily-Park-Orlando.d553248621532654336.Vacation-Attraction) - [Car rental Orlando Airport (MCO) ](https://www.expedia.com/Car-Rentals-In-Orlando-Intl.d5194573.Car-Rental-Guide) - [Car rentals near Orlando ](https://www.expedia.com/Car-Rentals-In-Orlando.d178294.Car-Rental-Guide) - [Car rentals near Albin Polasek Museum and Sculpture Gardens ](https://www.expedia.com/Car-Rentals-In-Albin-Polasek-Museum-And-Sculpture-Gardens.d6154778.Car-Rental-Guide) - [Car rentals near Winter Park Corner Shopping Center ](https://www.expedia.com/Car-Rentals-In-Winter-Park-Corner-Shopping-Center.d553248621532654341.Car-Rental-Guide) - [Car rentals near Rollins College ](https://www.expedia.com/Car-Rentals-In-Rollins-College.d6154361.Car-Rental-Guide) - [Compact Car Rentals near Rollins College ](https://www.expedia.com/Compact-Car-Rentals-In-Rollins-College.d6154361-tCompact.Car-Rental-Guide-Class) - [Car rentals near Aloma ](https://www.expedia.com/Car-Rentals-In-Aloma.d553248635975863638.Car-Rental-Guide) - [Things to do in Orlando ](https://www.expedia.com/Things-To-Do-In-Orlando.d178294.Travel-Guide-Activities)