Title: 20 Best B&B in Winter Park, FL - Bed and Breakfast from $699 | 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 $678 nightly $699 total Apr 5 - Apr 6 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) ![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) ![Dining](https://images.trvl-media.com/lodging/114000000/113040000/113039700/113039630/635d6269.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 $894 nightly $1,006 total Apr 19 - Apr 20 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=2026-04-18&endDate=2026-04-19®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 ![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 "The pool areas were nice but over crowded. The food was good not great Nice young man named christian stopped us on our way out, just super friendly and gave us a ride with our luggage. The nicest employee, I encountered there although most of the staff was friendly. " [](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 "Good Orlando hotel. Value hotel." [](https://expedia.com/Orlando-Hotels-Caribe-Royale-Orlando.h40865.Hotel-Information) ![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 "Excellent " [](https://expedia.com/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information) ![Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/91c45539_y.jpg) ### Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando 10/10 Excellent "Easy check in. Rooms are super clean stocked with towels etc. There is an added daily fee for parking. So much to do at this resort from the pools to the activities. Food is great too. Centrally located close to all the parks in Orlando. We would definitely come back. " [](https://expedia.com/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information) ![DoubleTree by Hilton at the Entrance to Universal Orlando](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/cae40483_y.jpg) ### DoubleTree by Hilton at the Entrance to Universal Orlando 10/10 Excellent "My room was always clean. The cookies were amazing. The hotel is a short walk to Universal City Walk and major attractions." [](https://expedia.com/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.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 6/10 Okay "Clean room - however very minimal amenities. Same breakfast every day. " [](https://expedia.com/Orlando-Hotels-Fairfield-Inn-Suites-Lake-Buena-Vista-In-Marriott-Village.h470892.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 6/10 Okay "Towels thin Bathtub tired" [](https://expedia.com/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.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 "Our room was visibly updated and very clean. Perfect for myself and 2 teenage boys. The shower was unique with 2 different shower heads and great pressure. Beds were comfortable. Thermostat worked great. The location was perfect for visiting parks, specifically Universal for us. We had walking access to local restaurants and stores but also public transportation to other places. Would definitely stay again." [](https://expedia.com/Orlando-Hotels-Floridian-Express-Extended-Stay-Hotel.h26703.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 6/10 Okay "A lot of electrical outlets didn’t work, elevator was out the whole week we were there" [](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 | $699 | | Highest Price | $1,006 | ## 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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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)